From 86fb3656b3e6b63b467b5e81b1821a2d034cef07 Mon Sep 17 00:00:00 2001
From: klopez4212 <klopez4212@gmail.com>
Date: Mon, 15 Jun 2026 12:17:15 +0100
Subject: [PATCH 1/6] Polish direct message and members modals

---
 .../channels/lib/dmParticipantDisplay.ts      |  34 +
 .../channels/ui/ChannelMemberInviteCard.tsx   | 109 +--
 .../src/features/channels/ui/ChannelPane.tsx  |  41 +-
 .../features/channels/ui/ChannelScreen.tsx    |   2 +
 .../channels/ui/ChannelScreenHeader.tsx       |  80 +-
 .../features/channels/ui/MembersSidebar.tsx   | 631 +++++++++++++---
 .../channels/ui/MembersSidebarMemberCard.tsx  | 105 +--
 .../channels/useActiveChannelHeader.ts        |  54 +-
 .../messages/lib/useRichTextEditor.ts         |   2 +-
 .../src/features/messages/ui/MessageRow.tsx   |   4 +-
 .../messages/ui/MessageThreadSummaryRow.tsx   |  15 +-
 .../features/messages/ui/MessageTimeline.tsx  |  71 +-
 .../messages/ui/TimelineMessageList.tsx       |   3 +
 .../src/features/sidebar/lib/channelLabels.ts |   7 +-
 .../src/features/sidebar/ui/AppSidebar.tsx    |  40 +-
 .../sidebar/ui/NewDirectMessageDialog.tsx     | 698 ++++++++++++++----
 .../features/sidebar/ui/SidebarSection.tsx    |  39 +-
 desktop/src/shared/styles/globals.css         |   2 +-
 desktop/src/shared/ui/dialog.tsx              |  26 +-
 desktop/src/shared/ui/sidebar.tsx             |   4 +-
 desktop/tests/e2e/channels.spec.ts            | 164 +++-
 desktop/tests/e2e/messaging.spec.ts           |  11 +
 22 files changed, 1638 insertions(+), 504 deletions(-)
 create mode 100644 desktop/src/features/channels/lib/dmParticipantDisplay.ts

diff --git a/desktop/src/features/channels/lib/dmParticipantDisplay.ts b/desktop/src/features/channels/lib/dmParticipantDisplay.ts
new file mode 100644
index 000000000..edbe7d582
--- /dev/null
+++ b/desktop/src/features/channels/lib/dmParticipantDisplay.ts
@@ -0,0 +1,34 @@
+export const DM_PARTICIPANT_PREVIEW_LIMIT = 3;
+
+export type DmParticipantDisplay = {
+  displayName: string;
+};
+
+export function getDmParticipantPreview<T>(participants: readonly T[]) {
+  const visibleParticipants = participants.slice(
+    0,
+    DM_PARTICIPANT_PREVIEW_LIMIT,
+  );
+
+  return {
+    hiddenCount: Math.max(
+      0,
+      participants.length - DM_PARTICIPANT_PREVIEW_LIMIT,
+    ),
+    visibleParticipants,
+  };
+}
+
+export function formatDmParticipantDisplayName(
+  participants: readonly DmParticipantDisplay[],
+) {
+  const { hiddenCount, visibleParticipants } =
+    getDmParticipantPreview(participants);
+  const names = visibleParticipants.map(
+    (participant) => participant.displayName,
+  );
+
+  return hiddenCount > 0
+    ? [...names, `+${hiddenCount} more`].join(", ")
+    : names.join(", ");
+}
diff --git a/desktop/src/features/channels/ui/ChannelMemberInviteCard.tsx b/desktop/src/features/channels/ui/ChannelMemberInviteCard.tsx
index 7f093294d..e31004a97 100644
--- a/desktop/src/features/channels/ui/ChannelMemberInviteCard.tsx
+++ b/desktop/src/features/channels/ui/ChannelMemberInviteCard.tsx
@@ -1,4 +1,4 @@
-import { ChevronDown, Search, UserPlus, X } from "lucide-react";
+import { Search, UserPlus, X } from "lucide-react";
 import * as React from "react";
 
 import { formatPubkey } from "@/features/channels/lib/memberUtils";
@@ -9,10 +9,8 @@ import type {
   ChannelMember,
   UserSearchResult,
 } from "@/shared/api/types";
-import { cn } from "@/shared/lib/cn";
 import { Button } from "@/shared/ui/button";
 import { Input } from "@/shared/ui/input";
-import { Textarea } from "@/shared/ui/textarea";
 import { UserAvatar } from "@/shared/ui/UserAvatar";
 
 function formatSearchUserName(user: UserSearchResult) {
@@ -23,17 +21,6 @@ function formatSearchUserName(user: UserSearchResult) {
   );
 }
 
-function formatSearchUserSecondary(user: UserSearchResult) {
-  const displayName = user.displayName?.trim();
-  const nip05Handle = user.nip05Handle?.trim();
-
-  if (displayName && nip05Handle) {
-    return nip05Handle;
-  }
-
-  return formatPubkey(user.pubkey);
-}
-
 export function ChannelMemberInviteCard({
   canAssignElevatedRoles,
   existingMembers,
@@ -52,10 +39,7 @@ export function ChannelMemberInviteCard({
   open: boolean;
   requestErrorMessage?: string | null;
 }) {
-  const [invitePubkeys, setInvitePubkeys] = React.useState("");
   const [inviteQuery, setInviteQuery] = React.useState("");
-  const [isDirectPubkeyEntryOpen, setIsDirectPubkeyEntryOpen] =
-    React.useState(false);
   const [selectedInvitees, setSelectedInvitees] = React.useState<
     UserSearchResult[]
   >([]);
@@ -122,36 +106,17 @@ export function ChannelMemberInviteCard({
 
   React.useEffect(() => {
     if (!open) {
-      setInvitePubkeys("");
       setInviteQuery("");
-      setIsDirectPubkeyEntryOpen(false);
       setSelectedInvitees([]);
       setSubmissionErrors([]);
     }
   }, [open]);
 
-  const parsedInvitePubkeys = React.useMemo(
-    () =>
-      invitePubkeys
-        .split(/[\s,]+/)
-        .map((value) => value.trim())
-        .filter((value) => value.length > 0),
-    [invitePubkeys],
-  );
-  const inviteTargets = [
-    ...new Set([
-      ...selectedInvitees.map((invitee) => invitee.pubkey),
-      ...parsedInvitePubkeys,
-    ]),
-  ];
-  const directEntryLabel =
-    parsedInvitePubkeys.length > 0 && !isDirectPubkeyEntryOpen
-      ? `Direct pubkey entry (${parsedInvitePubkeys.length} ready)`
-      : "Direct pubkey entry";
+  const inviteTargets = selectedInvitees.map((invitee) => invitee.pubkey);
 
   return (
     <form
-      className="space-y-2.5 rounded-xl border border-border/80 bg-muted/15 p-3"
+      className="space-y-2.5 rounded-xl border border-border/70 bg-background/70 p-3"
       onSubmit={(event) => {
         event.preventDefault();
         void onSubmit({
@@ -166,13 +131,6 @@ export function ChannelMemberInviteCard({
               (invitee) => !addedPubkeys.has(invitee.pubkey.toLowerCase()),
             ),
           );
-          const remainingPubkeys = parsedInvitePubkeys
-            .filter((pubkey) => !addedPubkeys.has(pubkey.toLowerCase()))
-            .join("\n");
-          setInvitePubkeys(remainingPubkeys);
-          if (remainingPubkeys.length > 0) {
-            setIsDirectPubkeyEntryOpen(true);
-          }
           setInviteQuery("");
           setSubmissionErrors(result.errors);
         });
@@ -202,7 +160,7 @@ export function ChannelMemberInviteCard({
               disabled={isPending}
               id="channel-management-search-users"
               onChange={(event) => setInviteQuery(event.target.value)}
-              placeholder="Search by name or NIP-05."
+              placeholder="Search people and agents"
               value={inviteQuery}
             />
           </div>
@@ -265,14 +223,14 @@ export function ChannelMemberInviteCard({
                           displayName={formatSearchUserName(result)}
                           size="xs"
                         />
-                        <div className="min-w-0">
-                          <p className="truncate text-sm font-medium leading-5">
-                            {formatSearchUserName(result)}
-                          </p>
-                          <p className="truncate text-xs text-muted-foreground">
-                            {formatSearchUserSecondary(result)}
-                          </p>
-                        </div>
+                        <p className="truncate text-sm font-medium leading-5">
+                          {formatSearchUserName(result)}
+                        </p>
+                        {result.isAgent ? (
+                          <span className="shrink-0 text-xs text-muted-foreground">
+                            agent
+                          </span>
+                        ) : null}
                       </div>
                       <span className="text-xs text-muted-foreground">Add</span>
                     </button>
@@ -292,49 +250,6 @@ export function ChannelMemberInviteCard({
           </p>
         ) : null}
       </div>
-      <div className="space-y-2">
-        <button
-          aria-controls="channel-management-direct-pubkeys-panel"
-          aria-expanded={isDirectPubkeyEntryOpen}
-          className="inline-flex items-center gap-1.5 text-xs font-medium text-muted-foreground transition-colors hover:text-foreground"
-          data-testid="channel-management-toggle-direct-pubkeys"
-          onClick={() => {
-            setIsDirectPubkeyEntryOpen((current) => !current);
-          }}
-          type="button"
-        >
-          <ChevronDown
-            className={cn(
-              "h-4 w-4 transition-transform",
-              isDirectPubkeyEntryOpen && "rotate-180",
-            )}
-          />
-          <span>{directEntryLabel}</span>
-        </button>
-
-        {isDirectPubkeyEntryOpen ? (
-          <div
-            className="space-y-1.5 rounded-lg border border-dashed border-border/80 bg-background/70 p-2.5"
-            id="channel-management-direct-pubkeys-panel"
-          >
-            <label className="sr-only" htmlFor="channel-management-add-pubkeys">
-              Paste pubkeys
-            </label>
-            <p className="text-xs text-muted-foreground">
-              For exact pubkeys when search is not the right fit.
-            </p>
-            <Textarea
-              className="min-h-24"
-              data-testid="channel-management-add-pubkeys"
-              disabled={isPending}
-              id="channel-management-add-pubkeys"
-              onChange={(event) => setInvitePubkeys(event.target.value)}
-              placeholder="Paste one or more pubkeys, separated by spaces, commas, or new lines."
-              value={invitePubkeys}
-            />
-          </div>
-        ) : null}
-      </div>
       <div className="flex flex-wrap items-center justify-between gap-2">
         <label className="sr-only" htmlFor="channel-member-role">
           Role
diff --git a/desktop/src/features/channels/ui/ChannelPane.tsx b/desktop/src/features/channels/ui/ChannelPane.tsx
index df53071ae..2196b4939 100644
--- a/desktop/src/features/channels/ui/ChannelPane.tsx
+++ b/desktop/src/features/channels/ui/ChannelPane.tsx
@@ -7,6 +7,7 @@ import { DropZoneOverlay } from "@/features/messages/ui/ComposerAttachments";
 import { MessageThreadPanel } from "@/features/messages/ui/MessageThreadPanel";
 import { MessageTimeline } from "@/features/messages/ui/MessageTimeline";
 import type { ImetaMedia } from "@/features/messages/lib/imetaMediaMarkdown";
+import { formatDmParticipantDisplayName } from "@/features/channels/lib/dmParticipantDisplay";
 import { useComposerHeightPadding } from "@/features/messages/ui/useComposerHeightPadding";
 import { TypingIndicatorRow } from "@/features/messages/ui/TypingIndicatorRow";
 import type { TypingIndicatorEntry } from "@/features/messages/useChannelTyping";
@@ -43,6 +44,7 @@ import type { Channel } from "@/shared/api/types";
 import { useIsThreadPanelOverlay } from "@/shared/hooks/use-mobile";
 import { channelChrome } from "@/shared/layout/chromeLayout";
 import { cn } from "@/shared/lib/cn";
+import { normalizePubkey } from "@/shared/lib/pubkey";
 
 type ChannelPaneProps = {
   activeChannel: Channel | null;
@@ -496,30 +498,40 @@ export const ChannelPane = React.memo(function ChannelPane({
         pubkey,
       }),
     );
-    const otherParticipants = currentPubkey
+    const normalizedCurrentPubkey = currentPubkey
+      ? normalizePubkey(currentPubkey)
+      : null;
+    const otherParticipants = normalizedCurrentPubkey
       ? participants.filter(
           (participant) =>
-            participant.pubkey.toLowerCase() !== currentPubkey.toLowerCase(),
+            normalizePubkey(participant.pubkey) !== normalizedCurrentPubkey,
         )
       : participants;
-    const [participant] =
+    const displayParticipants =
       otherParticipants.length > 0 ? otherParticipants : participants;
 
-    if (!participant) {
+    if (displayParticipants.length === 0) {
       return null;
     }
 
-    const profile = profiles?.[participant.pubkey.toLowerCase()] ?? null;
-    const displayName = resolveUserLabel({
-      currentPubkey,
-      fallbackName: participant.fallbackName,
-      profiles,
-      pubkey: participant.pubkey,
+    const introParticipants = displayParticipants.map((participant) => {
+      const profile = profiles?.[normalizePubkey(participant.pubkey)] ?? null;
+
+      return {
+        avatarUrl: profile?.avatarUrl ?? null,
+        displayName: resolveUserLabel({
+          currentPubkey,
+          fallbackName: participant.fallbackName,
+          profiles,
+          pubkey: participant.pubkey,
+        }),
+        pubkey: participant.pubkey,
+      };
     });
 
     return {
-      avatarUrl: profile?.avatarUrl ?? null,
-      displayName,
+      displayName: formatDmParticipantDisplayName(introParticipants),
+      participants: introParticipants,
     };
   }, [activeChannel, currentPubkey, profiles]);
 
@@ -746,7 +758,10 @@ export const ChannelPane = React.memo(function ChannelPane({
                       : activeChannel?.channelType === "forum"
                         ? "Forum posting is not wired in this pass."
                         : activeChannel
-                          ? `Message #${activeChannel.name}`
+                          ? activeChannel.channelType === "dm" &&
+                            directMessageIntro
+                            ? `Message ${directMessageIntro.displayName}`
+                            : `Message #${activeChannel.name}`
                           : "Select a channel"
                   }
                   showTopBorder={false}
diff --git a/desktop/src/features/channels/ui/ChannelScreen.tsx b/desktop/src/features/channels/ui/ChannelScreen.tsx
index 9e4737957..15f93e090 100644
--- a/desktop/src/features/channels/ui/ChannelScreen.tsx
+++ b/desktop/src/features/channels/ui/ChannelScreen.tsx
@@ -136,6 +136,7 @@ export function ChannelScreen({
   const {
     activeChannelTitle,
     activeDmAvatarUrl,
+    activeDmHeaderParticipants,
     activeDmPresenceStatus,
     activeChannelEphemeralDisplay,
   } = useActiveChannelHeader(activeChannel, currentPubkey);
@@ -528,6 +529,7 @@ export function ChannelScreen({
       activeChannelTitle={activeChannelTitle}
       actionsVariant={shouldCompactHeaderActions ? "compact" : "inline"}
       activeDmAvatarUrl={activeDmAvatarUrl}
+      activeDmHeaderParticipants={activeDmHeaderParticipants}
       activeDmPresenceStatus={activeDmPresenceStatus}
       chromeWrapperRef={channelHeaderChromeRef}
       currentPubkey={currentPubkey}
diff --git a/desktop/src/features/channels/ui/ChannelScreenHeader.tsx b/desktop/src/features/channels/ui/ChannelScreenHeader.tsx
index a873069f7..83d551259 100644
--- a/desktop/src/features/channels/ui/ChannelScreenHeader.tsx
+++ b/desktop/src/features/channels/ui/ChannelScreenHeader.tsx
@@ -3,12 +3,15 @@ import type * as React from "react";
 
 import { ChatHeader } from "@/features/chat/ui/ChatHeader";
 import type { EphemeralChannelDisplay } from "@/features/channels/lib/ephemeralChannel";
+import type { ActiveDmHeaderParticipant } from "@/features/channels/useActiveChannelHeader";
 import { getChannelDescription } from "@/features/channels/lib/channelDescription";
+import { getDmParticipantPreview } from "@/features/channels/lib/dmParticipantDisplay";
 import { ChannelHeaderStatusBadge } from "@/features/channels/ui/ChannelHeaderStatusBadge";
 import { ChannelMembersBar } from "@/features/channels/ui/ChannelMembersBar";
 import { ProfileAvatar } from "@/features/profile/ui/ProfileAvatar";
 import { Button } from "@/shared/ui/button";
 import type { Channel, PresenceStatus } from "@/shared/api/types";
+import { UserAvatar } from "@/shared/ui/UserAvatar";
 
 type ChannelScreenHeaderProps = {
   activeChannel: Channel | null;
@@ -16,6 +19,7 @@ type ChannelScreenHeaderProps = {
   activeChannelTitle: string;
   actionsVariant?: "inline" | "compact";
   activeDmAvatarUrl: string | null;
+  activeDmHeaderParticipants: ActiveDmHeaderParticipant[];
   activeDmPresenceStatus: PresenceStatus | null;
   chromeWrapperRef?: React.Ref<HTMLDivElement>;
   currentPubkey?: string;
@@ -34,6 +38,7 @@ export function ChannelScreenHeader({
   activeChannelTitle,
   actionsVariant = "inline",
   activeDmAvatarUrl,
+  activeDmHeaderParticipants,
   activeDmPresenceStatus,
   chromeWrapperRef,
   currentPubkey,
@@ -45,6 +50,9 @@ export function ChannelScreenHeader({
   onManageChannel,
   onToggleMembers,
 }: ChannelScreenHeaderProps) {
+  const isGroupDm =
+    activeChannel?.channelType === "dm" &&
+    activeDmHeaderParticipants.length > 1;
   const showJoinButton =
     activeChannel !== null &&
     !activeChannel.isMember &&
@@ -90,13 +98,19 @@ export function ChannelScreenHeader({
       description={getChannelDescription(activeChannel)}
       leadingContent={
         activeChannel?.channelType === "dm" ? (
-          <ProfileAvatar
-            avatarUrl={activeDmAvatarUrl}
-            className="h-6 w-6 rounded-full text-[10px]"
-            iconClassName="h-3.5 w-3.5"
-            label={activeChannelTitle}
-            testId="chat-header-dm-avatar"
-          />
+          isGroupDm ? (
+            <DmHeaderParticipantStack
+              participants={activeDmHeaderParticipants}
+            />
+          ) : (
+            <ProfileAvatar
+              avatarUrl={activeDmAvatarUrl}
+              className="h-6 w-6 rounded-full text-[10px]"
+              iconClassName="h-3.5 w-3.5"
+              label={activeChannelTitle}
+              testId="chat-header-dm-avatar"
+            />
+          )
         ) : undefined
       }
       statusBadge={
@@ -111,3 +125,55 @@ export function ChannelScreenHeader({
     />
   );
 }
+
+function DmHeaderParticipantStack({
+  participants,
+}: {
+  participants: ActiveDmHeaderParticipant[];
+}) {
+  const { hiddenCount, visibleParticipants } =
+    getDmParticipantPreview(participants);
+  const stackItemCount = visibleParticipants.length + (hiddenCount > 0 ? 1 : 0);
+
+  return (
+    <div
+      aria-hidden="true"
+      className="mr-1 flex shrink-0 items-center"
+      data-testid="chat-header-dm-avatar-stack"
+    >
+      {visibleParticipants.map((participant, index) => (
+        <div
+          className={index > 0 ? "-ml-2" : ""}
+          data-testid="chat-header-dm-avatar-stack-participant"
+          key={participant.pubkey}
+          style={{
+            zIndex: index + 1,
+            ...(index < stackItemCount - 1 && {
+              mask: "radial-gradient(circle 16px at calc(100% + 4px) 50%, transparent 99%, #fff 100%)",
+              WebkitMask:
+                "radial-gradient(circle 16px at calc(100% + 4px) 50%, transparent 99%, #fff 100%)",
+            }),
+          }}
+        >
+          <UserAvatar
+            avatarUrl={participant.avatarUrl}
+            className="h-7 w-7 text-[10px]"
+            displayName={participant.displayName}
+            size="sm"
+          />
+        </div>
+      ))}
+      {hiddenCount > 0 ? (
+        <div
+          className={visibleParticipants.length > 0 ? "-ml-2" : ""}
+          data-testid="chat-header-dm-avatar-stack-more"
+          style={{ zIndex: stackItemCount }}
+        >
+          <span className="flex h-7 w-7 items-center justify-center rounded-full bg-secondary font-semibold text-secondary-foreground shadow-xs">
+            <span className="text-[11px] leading-none">+{hiddenCount}</span>
+          </span>
+        </div>
+      ) : null}
+    </div>
+  );
+}
diff --git a/desktop/src/features/channels/ui/MembersSidebar.tsx b/desktop/src/features/channels/ui/MembersSidebar.tsx
index 834914321..c309b37fe 100644
--- a/desktop/src/features/channels/ui/MembersSidebar.tsx
+++ b/desktop/src/features/channels/ui/MembersSidebar.tsx
@@ -1,28 +1,36 @@
 import * as React from "react";
 import { useMutation, useQueryClient } from "@tanstack/react-query";
+import { Bot, UserRoundPlus, X } from "lucide-react";
 import {
   useAddChannelMembersMutation,
   useChannelMembersQuery,
 } from "@/features/channels/hooks";
 import { useUpdateManagedAgentMutation } from "@/features/agents/hooks";
 import { CreateAgentRespondToField } from "@/features/agents/ui/RespondToField";
+import { useIsArchivedPredicate } from "@/features/identity-archive/hooks";
 import { useClassifiedMembers } from "@/features/channels/lib/useClassifiedMembers";
 import {
   formatMemberName,
   formatPubkey,
 } from "@/features/channels/lib/memberUtils";
-import { useUsersBatchQuery } from "@/features/profile/hooks";
+import {
+  useUserSearchQuery,
+  useUsersBatchQuery,
+} from "@/features/profile/hooks";
 import { usePresenceQuery } from "@/features/presence/hooks";
 import { changeChannelMemberRole } from "@/shared/api/tauri";
 import type {
+  AddChannelMembersResult,
   Channel,
   ChannelMember,
   ManagedAgent,
   RespondToMode,
+  UserSearchResult,
 } from "@/shared/api/types";
 import { Button } from "@/shared/ui/button";
 import {
   Dialog,
+  DialogClose,
   DialogContent,
   DialogDescription,
   DialogHeader,
@@ -31,18 +39,74 @@ import {
 import { useProfilePanel } from "@/shared/context/ProfilePanelContext";
 import { useFeedbackToasts } from "@/shared/hooks/useToastEffect";
 import { normalizePubkey } from "@/shared/lib/pubkey";
-import {
-  Sheet,
-  SheetContent,
-  SheetDescription,
-  SheetHeader,
-  SheetTitle,
-} from "@/shared/ui/sheet";
+import { UserAvatar } from "@/shared/ui/UserAvatar";
 import { MembersSidebarAgentControls } from "./MembersSidebarAgentControls";
-import { ChannelMemberInviteCard } from "./ChannelMemberInviteCard";
 import { MembersSidebarMemberCard } from "./MembersSidebarMemberCard";
 import { useMembersSidebarActions } from "./useMembersSidebarActions";
 
+const MEMBERS_SEARCH_SHELL_CLASS =
+  "group/search mt-4 flex cursor-text items-center gap-3 rounded-xl border border-input bg-background px-3 py-2.5 transition-colors duration-150 ease-out hover:border-muted-foreground/40 hover:bg-muted/70 focus-within:border-muted-foreground/50 focus-within:bg-muted/70";
+const MEMBERS_SEARCH_INPUT_CLASS =
+  "block h-6 min-w-0 flex-1 border-0 bg-transparent p-0 text-sm leading-5 text-muted-foreground/55 shadow-none caret-foreground outline-none transition-colors duration-150 ease-out placeholder:text-muted-foreground/55 group-hover/search:text-muted-foreground group-hover/search:placeholder:text-muted-foreground group-focus-within/search:text-foreground group-focus-within/search:placeholder:text-foreground";
+const MEMBER_ADD_RESULT_LIMIT = 50;
+
+function formatAddCandidateName(user: UserSearchResult) {
+  return (
+    user.displayName?.trim() ||
+    user.nip05Handle?.trim() ||
+    formatPubkey(user.pubkey)
+  );
+}
+
+function scoreAddCandidate(user: UserSearchResult, query: string) {
+  if (query.length === 0) {
+    return null;
+  }
+
+  const labels = [
+    formatAddCandidateName(user),
+    user.nip05Handle?.trim() ?? "",
+    user.isAgent ? "agent" : "",
+  ];
+
+  for (const label of labels) {
+    const lower = label.toLowerCase();
+    if (lower.startsWith(query)) return 0;
+    if (lower.split(/[\s\-_]+/).some((word) => word.startsWith(query))) {
+      return 1;
+    }
+    if (lower.includes(query)) return 2;
+  }
+
+  const pubkey = normalizePubkey(user.pubkey);
+  if (pubkey.startsWith(query)) return 3;
+  if (pubkey.includes(query)) return 4;
+
+  return null;
+}
+
+function memberModalRoleRank(member: ChannelMember) {
+  if (member.role === "owner") return 0;
+  if (member.role === "admin") return 1;
+  return 2;
+}
+
+function compareMembersForModal(
+  currentPubkey: string | undefined,
+  left: ChannelMember,
+  right: ChannelMember,
+) {
+  const rankDelta = memberModalRoleRank(left) - memberModalRoleRank(right);
+  if (rankDelta !== 0) {
+    return rankDelta;
+  }
+
+  if (currentPubkey && left.pubkey === currentPubkey) return -1;
+  if (currentPubkey && right.pubkey === currentPubkey) return 1;
+
+  return formatMemberName(left).localeCompare(formatMemberName(right));
+}
+
 type MembersSidebarProps = {
   channel: Channel | null;
   currentPubkey?: string;
@@ -60,6 +124,11 @@ export function MembersSidebar({
 }: MembersSidebarProps) {
   const channelId = channel?.id ?? null;
   const queryClient = useQueryClient();
+  const searchInputRef = React.useRef<HTMLInputElement>(null);
+  const [searchQuery, setSearchQuery] = React.useState("");
+  const [inviteSubmissionErrors, setInviteSubmissionErrors] = React.useState<
+    AddChannelMembersResult["errors"]
+  >([]);
   const membersQuery = useChannelMembersQuery(channelId, open);
   const addMembersMutation = useAddChannelMembersMutation(channelId);
   const changeRoleMutation = useMutation({
@@ -79,8 +148,24 @@ export function MembersSidebar({
       : null;
 
   const rawMembers = membersQuery.data ?? [];
-  const { people, bots, archived, isBot, isMyBot, managedAgentsQuery } =
-    useClassifiedMembers(rawMembers, currentPubkey);
+  const selfMember =
+    rawMembers.find((member) => member.pubkey === currentPubkey) ?? null;
+  const {
+    people,
+    bots,
+    archived,
+    isBot,
+    isMyBot,
+    managedAgentsQuery,
+    relayAgentsQuery,
+  } = useClassifiedMembers(rawMembers, currentPubkey);
+  const activeMembers = React.useMemo(
+    () =>
+      [...people, ...bots].sort((left, right) =>
+        compareMembersForModal(currentPubkey, left, right),
+      ),
+    [bots, currentPubkey, people],
+  );
 
   const allMemberPubkeys = React.useMemo(
     () => rawMembers.map((member) => member.pubkey),
@@ -92,9 +177,193 @@ export function MembersSidebar({
   const memberProfilesQuery = useUsersBatchQuery(allMemberPubkeys, {
     enabled: open && rawMembers.length > 0,
   });
+  const normalizedSearchQuery = searchQuery.trim().toLowerCase();
+  const deferredSearchQuery = React.useDeferredValue(searchQuery.trim());
+  const normalizedDeferredSearchQuery = deferredSearchQuery.toLowerCase();
+  const filteredActiveMembers = React.useMemo(() => {
+    if (!normalizedSearchQuery) {
+      return activeMembers;
+    }
+
+    const profiles = memberProfilesQuery.data?.profiles ?? {};
+
+    return activeMembers.filter((member) => {
+      const normalizedPubkey = normalizePubkey(member.pubkey);
+      const profile = profiles[normalizedPubkey] ?? null;
+      const memberIsBot = isBot(member);
+      const labels = [
+        formatMemberName(member, currentPubkey),
+        member.displayName ?? "",
+        profile?.displayName ?? "",
+        memberIsBot ? "agent" : "",
+        member.role,
+        normalizedPubkey,
+      ];
+
+      return labels.some((label) =>
+        label.toLowerCase().includes(normalizedSearchQuery),
+      );
+    });
+  }, [
+    activeMembers,
+    currentPubkey,
+    isBot,
+    memberProfilesQuery.data?.profiles,
+    normalizedSearchQuery,
+  ]);
+  const memberPubkeys = React.useMemo(
+    () => new Set(rawMembers.map((member) => normalizePubkey(member.pubkey))),
+    [rawMembers],
+  );
+  const canAddMembers =
+    (selfMember !== null || channel?.visibility === "open") &&
+    channel?.channelType !== "dm";
+  const userSearchQuery = useUserSearchQuery(deferredSearchQuery, {
+    allowEmpty: false,
+    enabled: open && canAddMembers && deferredSearchQuery.length > 0,
+    limit: MEMBER_ADD_RESULT_LIMIT,
+  });
+  const isArchivedDiscovery = useIsArchivedPredicate();
+  const addSearchResults = React.useMemo(() => {
+    if (!canAddMembers || normalizedDeferredSearchQuery.length === 0) {
+      return [];
+    }
+
+    const candidatesByPubkey = new Map<string, UserSearchResult>();
+    const eligibleAgentPubkeys = new Set([
+      ...(managedAgentsQuery.data ?? []).map((agent) =>
+        normalizePubkey(agent.pubkey),
+      ),
+      ...(relayAgentsQuery.data ?? [])
+        .filter((agent) => agent.respondTo === "anyone")
+        .map((agent) => normalizePubkey(agent.pubkey)),
+    ]);
+
+    const addCandidate = (candidate: UserSearchResult) => {
+      const pubkey = normalizePubkey(candidate.pubkey);
+      if (
+        memberPubkeys.has(pubkey) ||
+        isArchivedDiscovery(pubkey) ||
+        (candidate.isAgent && !eligibleAgentPubkeys.has(pubkey))
+      ) {
+        return;
+      }
+
+      const current = candidatesByPubkey.get(pubkey);
+      if (!current) {
+        candidatesByPubkey.set(pubkey, { ...candidate, pubkey });
+        return;
+      }
+
+      const candidateName = candidate.displayName?.trim() || null;
+      const currentName = current.displayName?.trim() || null;
+
+      candidatesByPubkey.set(pubkey, {
+        pubkey,
+        avatarUrl: current.avatarUrl ?? candidate.avatarUrl ?? null,
+        displayName:
+          candidate.isAgent && candidateName
+            ? candidateName
+            : current.isAgent
+              ? currentName
+              : (currentName ?? candidateName),
+        nip05Handle: current.nip05Handle ?? candidate.nip05Handle ?? null,
+        isAgent: current.isAgent || candidate.isAgent,
+      });
+    };
+
+    for (const user of userSearchQuery.data ?? []) {
+      addCandidate(user);
+    }
+
+    for (const agent of relayAgentsQuery.data ?? []) {
+      if (agent.respondTo !== "anyone") {
+        continue;
+      }
+
+      addCandidate({
+        pubkey: agent.pubkey,
+        displayName: agent.name,
+        avatarUrl: null,
+        nip05Handle: null,
+        isAgent: true,
+      });
+    }
+
+    for (const agent of managedAgentsQuery.data ?? []) {
+      addCandidate({
+        pubkey: agent.pubkey,
+        displayName: agent.name,
+        avatarUrl: null,
+        nip05Handle: null,
+        isAgent: true,
+      });
+    }
+
+    return [...candidatesByPubkey.values()]
+      .map((candidate, order) => ({
+        candidate,
+        order,
+        score: scoreAddCandidate(candidate, normalizedDeferredSearchQuery),
+      }))
+      .filter(
+        (item): item is typeof item & { score: number } => item.score !== null,
+      )
+      .sort(
+        (left, right) =>
+          left.score - right.score ||
+          formatAddCandidateName(left.candidate).localeCompare(
+            formatAddCandidateName(right.candidate),
+          ) ||
+          left.order - right.order,
+      )
+      .slice(0, MEMBER_ADD_RESULT_LIMIT)
+      .map(({ candidate }) => candidate);
+  }, [
+    canAddMembers,
+    isArchivedDiscovery,
+    managedAgentsQuery.data,
+    memberPubkeys,
+    normalizedDeferredSearchQuery,
+    relayAgentsQuery.data,
+    userSearchQuery.data,
+  ]);
+  const isAddSearchLoading =
+    userSearchQuery.isLoading ||
+    managedAgentsQuery.isLoading ||
+    relayAgentsQuery.isLoading;
+  const filteredArchivedMembers = React.useMemo(() => {
+    if (!normalizedSearchQuery) {
+      return archived;
+    }
+
+    const profiles = memberProfilesQuery.data?.profiles ?? {};
+
+    return archived.filter((member) => {
+      const normalizedPubkey = normalizePubkey(member.pubkey);
+      const profile = profiles[normalizedPubkey] ?? null;
+      const memberIsBot = isBot(member);
+      const labels = [
+        formatMemberName(member, currentPubkey),
+        member.displayName ?? "",
+        profile?.displayName ?? "",
+        memberIsBot ? "agent" : "",
+        member.role,
+        normalizedPubkey,
+      ];
+
+      return labels.some((label) =>
+        label.toLowerCase().includes(normalizedSearchQuery),
+      );
+    });
+  }, [
+    archived,
+    currentPubkey,
+    isBot,
+    memberProfilesQuery.data?.profiles,
+    normalizedSearchQuery,
+  ]);
 
-  const selfMember =
-    rawMembers.find((member) => member.pubkey === currentPubkey) ?? null;
   const canManageMembers =
     selfMember?.role === "owner" || selfMember?.role === "admin";
   const isArchived =
@@ -180,10 +449,30 @@ export function MembersSidebar({
   const [editRespondToAgent, setEditRespondToAgent] =
     React.useState<ManagedAgent | null>(null);
 
+  React.useEffect(() => {
+    if (!open) {
+      setSearchQuery("");
+      setInviteSubmissionErrors([]);
+      return;
+    }
+
+    searchInputRef.current?.focus({ preventScroll: true });
+  }, [open]);
+
   if (!channel) {
     return null;
   }
 
+  async function handleAddSearchResult(user: UserSearchResult) {
+    setInviteSubmissionErrors([]);
+
+    const result = await addMembersMutation.mutateAsync({
+      pubkeys: [user.pubkey],
+      role: user.isAgent ? "bot" : "member",
+    });
+    setInviteSubmissionErrors(result.errors);
+  }
+
   function renderMemberCard(member: ChannelMember, memberIsBot: boolean) {
     return (
       <MembersSidebarMemberCard
@@ -231,95 +520,151 @@ export function MembersSidebar({
 
   return (
     <>
-      <Sheet onOpenChange={onOpenChange} open={open}>
-        <SheetContent
-          className="flex w-full flex-col gap-0 overflow-hidden border-l border-border/80 bg-background p-0 sm:max-w-md"
+      <Dialog onOpenChange={onOpenChange} open={open}>
+        <DialogContent
+          aria-describedby={undefined}
+          className="max-w-xl gap-0 overflow-hidden border-0 px-6 pb-0 pt-6"
           data-testid="members-sidebar"
-          side="right"
+          onOpenAutoFocus={(event) => {
+            event.preventDefault();
+            searchInputRef.current?.focus({ preventScroll: true });
+          }}
+          showCloseButton={false}
         >
-          <SheetHeader className="relative z-10 space-y-2 bg-background/25 px-6 py-6 text-left backdrop-blur-xl supports-[backdrop-filter]:bg-background/20">
-            <SheetTitle>Members</SheetTitle>
-            <SheetDescription>
-              People and bots in {channel.name}.
-            </SheetDescription>
-          </SheetHeader>
-
-          <div className="flex-1 space-y-6 overflow-y-auto px-6 py-6">
-            {(selfMember !== null || channel.visibility === "open") &&
-            channel.channelType !== "dm" ? (
-              <ChannelMemberInviteCard
-                canAssignElevatedRoles={canManageMembers}
-                existingMembers={rawMembers}
-                isPending={addMembersMutation.isPending}
-                onSubmit={(input) => addMembersMutation.mutateAsync(input)}
-                open={open}
-                requestErrorMessage={
-                  addMembersMutation.error instanceof Error
-                    ? addMembersMutation.error.message
-                    : null
+          <DialogHeader className="space-y-0 pb-5">
+            <div className="flex items-center justify-between gap-4">
+              <DialogTitle>Channel members</DialogTitle>
+              <DialogClose className="flex h-8 w-8 shrink-0 items-center justify-center rounded-md text-muted-foreground transition-colors duration-150 ease-out hover:bg-accent hover:text-accent-foreground focus:outline-hidden focus:ring-1 focus:ring-ring">
+                <X className="h-4 w-4" />
+                <span className="sr-only">Close</span>
+              </DialogClose>
+            </div>
+            <label
+              className={MEMBERS_SEARCH_SHELL_CLASS}
+              htmlFor="channel-management-search-users"
+            >
+              <UserRoundPlus className="h-4 w-4 shrink-0 text-muted-foreground/55 transition-colors duration-150 ease-out group-hover/search:text-muted-foreground group-focus-within/search:text-foreground" />
+              <input
+                autoCapitalize="none"
+                autoCorrect="off"
+                className={MEMBERS_SEARCH_INPUT_CLASS}
+                data-testid="channel-management-search-users"
+                disabled={addMembersMutation.isPending || isArchived}
+                id="channel-management-search-users"
+                onChange={(event) => {
+                  setSearchQuery(event.target.value);
+                }}
+                onKeyDown={(event) => {
+                  if (event.key !== "Enter" || addSearchResults.length === 0) {
+                    return;
+                  }
+
+                  event.preventDefault();
+                  void handleAddSearchResult(addSearchResults[0]);
+                }}
+                placeholder={
+                  canAddMembers
+                    ? "Add people and agents"
+                    : "Search people and agents"
                 }
+                ref={searchInputRef}
+                spellCheck={false}
+                type="text"
+                value={searchQuery}
               />
-            ) : null}
+            </label>
+          </DialogHeader>
 
-            <section className="space-y-2.5">
-              <div className="flex items-center justify-between gap-2">
-                <h2 className="text-sm font-semibold tracking-tight">People</h2>
-                <span className="rounded-full bg-muted px-2 py-0.5 text-[11px] font-medium text-muted-foreground">
-                  {people.length}
-                </span>
-              </div>
-              <div className="space-y-2" data-testid="members-sidebar-people">
-                {people.length > 0 ? (
-                  people.map((member) => renderMemberCard(member, false))
-                ) : (
-                  <p className="text-sm text-muted-foreground">
-                    {membersQuery.isLoading
-                      ? "Loading members..."
-                      : "No people found."}
-                  </p>
-                )}
-              </div>
-            </section>
-
-            <section className="space-y-2.5">
-              <div className="flex items-center gap-2">
-                <h2 className="text-sm font-semibold tracking-tight">Bots</h2>
-                <span className="rounded-full bg-muted px-2 py-0.5 text-[11px] font-medium text-muted-foreground">
-                  {bots.length}
-                </span>
-                {hasControllableManagedBots ? (
-                  <MembersSidebarAgentControls
-                    canBulkRemove={hasRemovableManagedBots}
-                    canBulkRespawn={hasControllableManagedBots}
-                    canBulkStop={hasStoppableManagedBots}
-                    disabled={isActionPending || isArchived}
-                    onRemoveAll={() => {
-                      void handleRemoveAll();
-                    }}
-                    onRespawnAll={() => {
-                      void handleRespawnAll();
-                    }}
-                    onStopAll={() => {
-                      void handleStopAll();
-                    }}
-                  />
-                ) : null}
-              </div>
-              <div className="space-y-2" data-testid="members-sidebar-bots">
-                {bots.length > 0 ? (
-                  bots.map((member) => renderMemberCard(member, true))
+          <div className="max-h-[calc(100vh-12rem)] overflow-y-auto pb-6">
+            <section>
+              <div
+                className="h-[min(50vh,24rem)] overflow-y-auto rounded-xl border border-border/70 bg-background/70"
+                data-testid="members-sidebar-people"
+              >
+                <SearchResultSectionTitle
+                  action={
+                    hasControllableManagedBots ? (
+                      <MembersSidebarAgentControls
+                        canBulkRemove={hasRemovableManagedBots}
+                        canBulkRespawn={hasControllableManagedBots}
+                        canBulkStop={hasStoppableManagedBots}
+                        disabled={isActionPending || isArchived}
+                        onRemoveAll={() => {
+                          void handleRemoveAll();
+                        }}
+                        onRespawnAll={() => {
+                          void handleRespawnAll();
+                        }}
+                        onStopAll={() => {
+                          void handleStopAll();
+                        }}
+                      />
+                    ) : null
+                  }
+                >
+                  {normalizedSearchQuery
+                    ? "Members"
+                    : `Members · ${activeMembers.length}`}
+                </SearchResultSectionTitle>
+                {normalizedSearchQuery ? (
+                  <div>
+                    {filteredActiveMembers.map((member) =>
+                      renderMemberCard(member, isBot(member)),
+                    )}
+                    {canAddMembers ? (
+                      <>
+                        {addSearchResults.length > 0 || isAddSearchLoading ? (
+                          <SearchResultSectionTitle>
+                            Not in this channel
+                          </SearchResultSectionTitle>
+                        ) : null}
+                        {addSearchResults.map((user) => (
+                          <AddMemberSearchResultRow
+                            disabled={
+                              addMembersMutation.isPending || isArchived
+                            }
+                            key={user.pubkey}
+                            onSelect={(selectedUser) => {
+                              void handleAddSearchResult(selectedUser);
+                            }}
+                            user={user}
+                          />
+                        ))}
+                        {isAddSearchLoading ? (
+                          <p className="px-4 py-3 text-sm text-muted-foreground">
+                            Searching...
+                          </p>
+                        ) : null}
+                      </>
+                    ) : null}
+                    {filteredActiveMembers.length === 0 &&
+                    addSearchResults.length === 0 &&
+                    !isAddSearchLoading ? (
+                      <p className="px-4 py-3 text-sm text-muted-foreground">
+                        No matching people or agents.
+                      </p>
+                    ) : null}
+                  </div>
+                ) : filteredActiveMembers.length > 0 ? (
+                  <div>
+                    {filteredActiveMembers.map((member) =>
+                      renderMemberCard(member, isBot(member)),
+                    )}
+                  </div>
                 ) : (
-                  <p className="text-sm text-muted-foreground">
+                  <p className="px-4 py-3 text-sm text-muted-foreground">
                     {membersQuery.isLoading
                       ? "Loading members..."
-                      : "No bots found."}
+                      : normalizedSearchQuery
+                        ? "No members match your search."
+                        : "No members found."}
                   </p>
                 )}
               </div>
             </section>
 
             {archived.length > 0 ? (
-              <section className="space-y-2.5">
+              <section className="mt-4">
                 <details
                   className="group/archived"
                   data-testid="members-sidebar-archived"
@@ -329,10 +674,10 @@ export function MembersSidebar({
                       Archived
                     </h2>
                     <span
-                      className="rounded-full bg-muted px-2 py-0.5 text-[11px] font-medium text-muted-foreground"
+                      className="text-muted-foreground"
                       data-testid="members-sidebar-archived-count"
                     >
-                      {archived.length}
+                      ({archived.length})
                     </span>
                     <span className="ml-auto text-xs text-muted-foreground transition-transform group-open/archived:rotate-90">
                       ▸
@@ -342,9 +687,14 @@ export function MembersSidebar({
                     className="mt-2 space-y-2"
                     data-testid="members-sidebar-archived-list"
                   >
-                    {archived.map((member) =>
+                    {filteredArchivedMembers.map((member) =>
                       renderMemberCard(member, isBot(member)),
                     )}
+                    {filteredArchivedMembers.length === 0 ? (
+                      <p className="text-sm text-muted-foreground">
+                        No archived members match your search.
+                      </p>
+                    ) : null}
                   </div>
                 </details>
               </section>
@@ -352,15 +702,31 @@ export function MembersSidebar({
 
             {changeRoleError ? (
               <p
-                className="text-sm text-destructive"
+                className="mt-4 text-sm text-destructive"
                 data-testid="members-sidebar-action-error"
               >
                 {changeRoleError}
               </p>
             ) : null}
+
+            {addMembersMutation.error instanceof Error ? (
+              <p className="mt-4 text-sm text-destructive">
+                {addMembersMutation.error.message}
+              </p>
+            ) : null}
+
+            {inviteSubmissionErrors.length > 0 ? (
+              <div className="mt-4 space-y-1 text-sm text-destructive">
+                {inviteSubmissionErrors.map((error) => (
+                  <p key={`${error.pubkey}-${error.error}`}>
+                    {formatPubkey(error.pubkey)}: {error.error}
+                  </p>
+                ))}
+              </div>
+            ) : null}
           </div>
-        </SheetContent>
-      </Sheet>
+        </DialogContent>
+      </Dialog>
       <EditRespondToDialog
         agent={editRespondToAgent}
         currentPubkey={currentPubkey}
@@ -373,6 +739,83 @@ export function MembersSidebar({
   );
 }
 
+function SearchResultSectionTitle({
+  action,
+  children,
+}: {
+  action?: React.ReactNode;
+  children: React.ReactNode;
+}) {
+  return (
+    <div className="sticky top-0 z-10 mr-3 flex min-h-9 items-center gap-2 bg-background/95 px-4 pb-1.5 pt-3 text-xs font-medium uppercase tracking-wide text-muted-foreground/75 backdrop-blur supports-[backdrop-filter]:bg-background/80">
+      <span>{children}</span>
+      {action ? (
+        <span className="normal-case tracking-normal">{action}</span>
+      ) : null}
+    </div>
+  );
+}
+
+function AddMemberSearchResultRow({
+  disabled,
+  onSelect,
+  user,
+}: {
+  disabled: boolean;
+  onSelect: (user: UserSearchResult) => void;
+  user: UserSearchResult;
+}) {
+  return (
+    <div
+      className="group/add-result relative isolate flex min-h-14 w-full items-center gap-3 px-4 py-3.5 text-left transition-colors duration-150 ease-out hover:bg-muted/40 focus-within:bg-muted/40"
+      data-testid={`channel-user-search-result-${user.pubkey}`}
+    >
+      <button
+        aria-label={`Select ${formatAddCandidateName(user)}`}
+        className="absolute inset-0 z-0 cursor-pointer focus-visible:outline-hidden focus-visible:ring-1 focus-visible:ring-ring"
+        disabled={disabled}
+        onClick={() => onSelect(user)}
+        type="button"
+      />
+      <UserAvatar
+        avatarUrl={user.avatarUrl}
+        className="pointer-events-none relative z-10 h-8 w-8 text-xs shadow-none"
+        displayName={formatAddCandidateName(user)}
+        size="sm"
+      />
+      <div className="pointer-events-none relative z-10 min-w-0 flex-1">
+        {user.isAgent ? (
+          <div className="flex min-w-0 items-center gap-2">
+            <span className="truncate text-sm font-medium tracking-tight">
+              {formatAddCandidateName(user)}
+            </span>
+            <span className="inline-flex shrink-0 items-center gap-1 text-xs text-muted-foreground">
+              <Bot aria-hidden="true" className="h-3 w-3" />
+              agent
+            </span>
+          </div>
+        ) : (
+          <span className="block truncate text-sm font-medium tracking-tight">
+            {formatAddCandidateName(user)}
+          </span>
+        )}
+      </div>
+      <Button
+        className="relative z-20 shrink-0"
+        disabled={disabled}
+        onClick={(event) => {
+          event.stopPropagation();
+          onSelect(user);
+        }}
+        size="sm"
+        type="button"
+      >
+        Add
+      </Button>
+    </div>
+  );
+}
+
 function EditRespondToDialog({
   agent,
   currentPubkey,
diff --git a/desktop/src/features/channels/ui/MembersSidebarMemberCard.tsx b/desktop/src/features/channels/ui/MembersSidebarMemberCard.tsx
index 69974cb30..3ba6310d1 100644
--- a/desktop/src/features/channels/ui/MembersSidebarMemberCard.tsx
+++ b/desktop/src/features/channels/ui/MembersSidebarMemberCard.tsx
@@ -1,5 +1,6 @@
 import {
   Activity,
+  Bot,
   Ellipsis,
   Pencil,
   Play,
@@ -31,7 +32,6 @@ import {
   DropdownMenuSubTrigger,
   DropdownMenuTrigger,
 } from "@/shared/ui/dropdown-menu";
-import { Badge } from "@/shared/ui/badge";
 
 type MembersSidebarMemberCardProps = {
   canChangeRole: boolean;
@@ -55,10 +55,14 @@ type MembersSidebarMemberCardProps = {
 
 function formatRoleLabel(member: ChannelMember, memberIsBot: boolean) {
   if (memberIsBot) {
-    return "Bot";
+    return "agent";
   }
 
-  return `${member.role[0]?.toUpperCase() ?? ""}${member.role.slice(1)}`;
+  if (member.role === "owner" || member.role === "admin") {
+    return member.role;
+  }
+
+  return null;
 }
 
 function formatRespondToLabel(agent: ManagedAgent) {
@@ -115,11 +119,11 @@ export function MembersSidebarMemberCard({
     : canRemoveMember || canChangeRole;
 
   const memberIdentity = (
-    <>
+    <div className="pointer-events-none relative z-10 flex min-w-0 flex-1 items-center gap-3">
       <div className="relative shrink-0">
         <ProfileAvatar
           avatarUrl={profileAvatarUrl ?? null}
-          className="h-9 w-9 text-[11px] shadow-none"
+          className="h-8 w-8 text-xs shadow-none"
           iconClassName="h-4 w-4"
           label={memberAvatarLabel}
         />
@@ -132,58 +136,73 @@ export function MembersSidebarMemberCard({
           </span>
         ) : null}
       </div>
-      <div className="min-w-0">
-        <div className="flex items-center gap-1.5">
-          <p className="truncate text-sm font-medium leading-5">
-            {memberLabel}
-          </p>
-          <Badge className="shrink-0" variant="secondary">
-            {roleLabel}
-          </Badge>
-          {managedAgent ? (
-            <>
-              <Badge
-                className="shrink-0"
-                data-testid={`sidebar-managed-agent-status-${member.pubkey}`}
-                variant="secondary"
-              >
-                {formatManagedAgentStatus(managedAgent)}
-              </Badge>
-              <Badge
-                className="shrink-0"
-                data-testid={`sidebar-managed-agent-respond-to-${member.pubkey}`}
-                variant="outline"
-              >
-                {formatRespondToLabel(managedAgent)}
-              </Badge>
-            </>
-          ) : null}
-        </div>
-        <p className="truncate font-mono text-[10px] text-muted-foreground/50">
-          {truncatePubkey(member.pubkey)}
-        </p>
+      <div className="min-w-0 flex-1">
+        {memberIsBot ? (
+          <div className="relative min-w-0">
+            <div className="flex min-w-0 items-center gap-2 transition-opacity duration-150 ease-out group-hover/member:opacity-0 group-focus-within/member:opacity-0">
+              <span className="truncate text-sm font-medium tracking-tight">
+                {memberLabel}
+              </span>
+              <span className="inline-flex shrink-0 items-center gap-1 text-xs text-muted-foreground">
+                <Bot aria-hidden="true" className="h-3 w-3" />
+                {roleLabel}
+              </span>
+            </div>
+            <span className="absolute inset-0 flex items-center opacity-0 transition-opacity duration-150 ease-out group-hover/member:opacity-100 group-focus-within/member:opacity-100">
+              <span className="truncate font-mono text-sm text-muted-foreground">
+                {truncatePubkey(member.pubkey)}
+              </span>
+            </span>
+          </div>
+        ) : (
+          <div className="flex min-w-0 items-center gap-2">
+            <span className="truncate text-sm font-medium tracking-tight">
+              {memberLabel}
+            </span>
+            {roleLabel ? (
+              <span className="inline-flex shrink-0 items-center text-xs text-muted-foreground">
+                {roleLabel}
+              </span>
+            ) : null}
+          </div>
+        )}
+        {managedAgent ? (
+          <span
+            className="sr-only"
+            data-testid={`sidebar-managed-agent-status-${member.pubkey}`}
+          >
+            {formatManagedAgentStatus(managedAgent)}
+          </span>
+        ) : null}
+        {managedAgent ? (
+          <span
+            className="sr-only"
+            data-testid={`sidebar-managed-agent-respond-to-${member.pubkey}`}
+          >
+            {formatRespondToLabel(managedAgent)}
+          </span>
+        ) : null}
       </div>
-    </>
+    </div>
   );
 
   return (
     <div
-      className="group flex items-center justify-between gap-3 rounded-lg px-3 py-2 transition-colors hover:bg-muted/40"
+      className="group/member relative isolate flex min-h-14 items-center gap-3 px-4 py-3.5 text-left transition-colors duration-150 ease-out hover:bg-muted/40 focus-within:bg-muted/40"
       data-testid={`sidebar-member-${member.pubkey}`}
     >
       {onOpenProfile ? (
         <button
           aria-label={`Open profile for ${memberLabel}`}
-          className="flex min-w-0 flex-1 items-center gap-3 text-left focus-visible:outline-none focus-visible:ring-2 focus-visible:ring-ring focus-visible:ring-offset-2 focus-visible:ring-offset-background rounded-md"
+          className="absolute inset-0 z-0 cursor-pointer focus-visible:outline-hidden focus-visible:ring-1 focus-visible:ring-ring"
           data-testid={`sidebar-member-open-profile-${member.pubkey}`}
           onClick={() => onOpenProfile(member.pubkey)}
           type="button"
-        >
-          {memberIdentity}
-        </button>
+        />
       ) : (
-        <div className="flex min-w-0 items-center gap-3">{memberIdentity}</div>
+        <span aria-hidden="true" className="absolute inset-0 z-0" />
       )}
+      {memberIdentity}
       {hasActions ? (
         <MemberActionsMenu
           canChangeRole={canChangeRole}
@@ -240,7 +259,7 @@ function MemberActionsMenu({
     <DropdownMenu modal={false}>
       <DropdownMenuTrigger asChild>
         <button
-          className="invisible flex h-7 w-7 shrink-0 items-center justify-center rounded-md text-muted-foreground group-hover:visible hover:bg-muted hover:text-foreground data-[state=open]:visible"
+          className="invisible relative z-20 flex h-7 w-7 shrink-0 items-center justify-center rounded-md text-muted-foreground group-hover/member:visible hover:bg-muted hover:text-foreground data-[state=open]:visible"
           data-testid={`sidebar-member-menu-${member.pubkey}`}
           type="button"
         >
diff --git a/desktop/src/features/channels/useActiveChannelHeader.ts b/desktop/src/features/channels/useActiveChannelHeader.ts
index 738f158c0..b7f2bc6da 100644
--- a/desktop/src/features/channels/useActiveChannelHeader.ts
+++ b/desktop/src/features/channels/useActiveChannelHeader.ts
@@ -3,22 +3,44 @@ import * as React from "react";
 import { useEphemeralChannelDisplay } from "@/features/channels/useEphemeralChannelDisplay";
 import { usePresenceQuery } from "@/features/presence/hooks";
 import { useUsersBatchQuery } from "@/features/profile/hooks";
+import { resolveUserLabel } from "@/features/profile/lib/identity";
 import { resolveChannelDisplayLabel } from "@/features/sidebar/lib/channelLabels";
 import type { Channel, PresenceStatus } from "@/shared/api/types";
+import { normalizePubkey } from "@/shared/lib/pubkey";
+
+export type ActiveDmHeaderParticipant = {
+  pubkey: string;
+  displayName: string;
+  avatarUrl: string | null;
+};
 
 export function useActiveChannelHeader(
   activeChannel: Channel | null,
   currentPubkey?: string,
 ) {
-  const activeDmParticipantPubkeys = React.useMemo(() => {
+  const activeDmParticipants = React.useMemo(() => {
     if (activeChannel?.channelType !== "dm") {
       return [];
     }
 
-    return activeChannel.participantPubkeys.filter(
-      (pubkey) => pubkey.toLowerCase() !== currentPubkey?.toLowerCase(),
-    );
+    const normalizedCurrentPubkey = currentPubkey
+      ? normalizePubkey(currentPubkey)
+      : null;
+
+    return activeChannel.participantPubkeys
+      .map((pubkey, index) => ({
+        fallbackName: activeChannel.participants[index] ?? null,
+        pubkey,
+      }))
+      .filter(
+        (participant) =>
+          normalizePubkey(participant.pubkey) !== normalizedCurrentPubkey,
+      );
   }, [activeChannel, currentPubkey]);
+  const activeDmParticipantPubkeys = React.useMemo(
+    () => activeDmParticipants.map((participant) => participant.pubkey),
+    [activeDmParticipants],
+  );
   const activeDmPresenceQuery = usePresenceQuery(activeDmParticipantPubkeys, {
     enabled: activeDmParticipantPubkeys.length > 0,
   });
@@ -36,9 +58,30 @@ export function useActiveChannelHeader(
   const activeDmAvatarUrl =
     activeDmParticipantPubkeys.length > 0
       ? (activeDmProfilesQuery.data?.profiles?.[
-          activeDmParticipantPubkeys[0]?.toLowerCase()
+          normalizePubkey(activeDmParticipantPubkeys[0] ?? "")
         ]?.avatarUrl ?? null)
       : null;
+  const activeDmHeaderParticipants = React.useMemo(
+    () =>
+      activeDmParticipants.map((participant) => {
+        const profile =
+          activeDmProfilesQuery.data?.profiles?.[
+            normalizePubkey(participant.pubkey)
+          ] ?? null;
+
+        return {
+          pubkey: participant.pubkey,
+          displayName: resolveUserLabel({
+            currentPubkey,
+            fallbackName: participant.fallbackName,
+            profiles: activeDmProfilesQuery.data?.profiles,
+            pubkey: participant.pubkey,
+          }),
+          avatarUrl: profile?.avatarUrl ?? null,
+        };
+      }),
+    [activeDmParticipants, activeDmProfilesQuery.data?.profiles, currentPubkey],
+  );
 
   return {
     activeChannelTitle: activeChannel
@@ -49,6 +92,7 @@ export function useActiveChannelHeader(
         )
       : "Channels",
     activeDmAvatarUrl,
+    activeDmHeaderParticipants,
     activeDmPresenceStatus,
     activeChannelEphemeralDisplay,
   };
diff --git a/desktop/src/features/messages/lib/useRichTextEditor.ts b/desktop/src/features/messages/lib/useRichTextEditor.ts
index e293aa9ab..ca8fc0aab 100644
--- a/desktop/src/features/messages/lib/useRichTextEditor.ts
+++ b/desktop/src/features/messages/lib/useRichTextEditor.ts
@@ -322,7 +322,7 @@ export function useRichTextEditor({
       editorProps: {
         attributes: {
           class:
-            "min-h-0 resize-none overflow-y-hidden border-0 bg-transparent px-0 py-0 text-sm leading-6 md:leading-6 shadow-none focus-visible:ring-0 caret-foreground outline-hidden prose-sm max-w-none",
+            "min-h-0 resize-none overflow-y-hidden border-0 bg-transparent px-0 py-0 text-sm leading-6 text-foreground md:leading-6 shadow-none focus-visible:ring-0 caret-foreground outline-hidden prose-sm max-w-none",
           "data-testid": "message-input",
         },
         // ArrowUp in an empty composer → edit your last message (Slack
diff --git a/desktop/src/features/messages/ui/MessageRow.tsx b/desktop/src/features/messages/ui/MessageRow.tsx
index d54b450dd..62effd2cc 100644
--- a/desktop/src/features/messages/ui/MessageRow.tsx
+++ b/desktop/src/features/messages/ui/MessageRow.tsx
@@ -46,6 +46,7 @@ export const MessageRow = React.memo(
     onUnfollowThread,
     profiles,
     searchQuery,
+    showDepthGuides = true,
     agentPubkeys,
     videoReviewContext,
   }: {
@@ -69,6 +70,7 @@ export const MessageRow = React.memo(
     onUnfollowThread?: (message: TimelineMessage) => void;
     profiles?: UserProfileLookup;
     searchQuery?: string;
+    showDepthGuides?: boolean;
     videoReviewContext?: VideoReviewContext;
   }) {
     const [expandedDiffId, setExpandedDiffId] = React.useState<string | null>(
@@ -345,7 +347,7 @@ export const MessageRow = React.memo(
         className="relative"
         style={indentPx > 0 ? { paddingLeft: `${indentPx}px` } : undefined}
       >
-        {depthGuideOffsets.length > 0 ? (
+        {showDepthGuides && depthGuideOffsets.length > 0 ? (
           <div
             aria-hidden
             className="pointer-events-none absolute left-0"
diff --git a/desktop/src/features/messages/ui/MessageThreadSummaryRow.tsx b/desktop/src/features/messages/ui/MessageThreadSummaryRow.tsx
index 6103bb403..3ab72ceeb 100644
--- a/desktop/src/features/messages/ui/MessageThreadSummaryRow.tsx
+++ b/desktop/src/features/messages/ui/MessageThreadSummaryRow.tsx
@@ -13,20 +13,22 @@ const NESTED_REPLY_OFFSET_PX = 28;
 function ParticipantAvatar({
   participant,
   index,
+  participantCount,
 }: {
   participant: TimelineThreadSummaryParticipant;
   index: number;
+  participantCount: number;
 }) {
   return (
     <div
       className={index > 0 ? "-ml-2" : ""}
       data-testid="message-thread-summary-participant"
       style={{
-        zIndex: 10 - index,
-        ...(index > 0 && {
-          mask: "radial-gradient(circle 16px at -4px 50%, transparent 99%, #fff 100%)",
+        zIndex: index + 1,
+        ...(index < participantCount - 1 && {
+          mask: "radial-gradient(circle 16px at calc(100% + 4px) 50%, transparent 99%, #fff 100%)",
           WebkitMask:
-            "radial-gradient(circle 16px at -4px 50%, transparent 99%, #fff 100%)",
+            "radial-gradient(circle 16px at calc(100% + 4px) 50%, transparent 99%, #fff 100%)",
         }),
       }}
     >
@@ -44,11 +46,13 @@ export function MessageThreadSummaryRow({
   depth = 0,
   message,
   onOpenThread,
+  showDepthGuides = true,
   summary,
 }: {
   depth?: number;
   message: TimelineMessage;
   onOpenThread: (message: TimelineMessage) => void;
+  showDepthGuides?: boolean;
   summary: TimelineThreadSummary;
 }) {
   const visibleDepth = Math.min(Math.max(depth, 0), 6);
@@ -74,7 +78,7 @@ export function MessageThreadSummaryRow({
 
   return (
     <div className="relative pb-1 pt-0.5">
-      {depthGuideOffsets.length > 0 ? (
+      {showDepthGuides && depthGuideOffsets.length > 0 ? (
         <div
           aria-hidden
           className="pointer-events-none absolute left-0"
@@ -108,6 +112,7 @@ export function MessageThreadSummaryRow({
               index={index}
               key={participant.id}
               participant={participant}
+              participantCount={summary.participants.length}
             />
           ))}
         </div>
diff --git a/desktop/src/features/messages/ui/MessageTimeline.tsx b/desktop/src/features/messages/ui/MessageTimeline.tsx
index 1fa347a20..b20073754 100644
--- a/desktop/src/features/messages/ui/MessageTimeline.tsx
+++ b/desktop/src/features/messages/ui/MessageTimeline.tsx
@@ -1,15 +1,16 @@
 import * as React from "react";
 import { ArrowDown, Hash } from "lucide-react";
 
+import { getDmParticipantPreview } from "@/features/channels/lib/dmParticipantDisplay";
 import type { TimelineMessage } from "@/features/messages/types";
 import type { UserProfileLookup } from "@/features/profile/lib/identity";
 import type { ChannelType } from "@/shared/api/types";
-import { ProfileAvatar } from "@/features/profile/ui/ProfileAvatar";
 import { cn } from "@/shared/lib/cn";
 import { channelChrome } from "@/shared/layout/chromeLayout";
 import { Button } from "@/shared/ui/button";
 import { Spinner } from "@/shared/ui/spinner";
 import { TooltipProvider } from "@/shared/ui/tooltip";
+import { UserAvatar } from "@/shared/ui/UserAvatar";
 import { TimelineSkeleton } from "./TimelineSkeleton";
 import { TimelineMessageList } from "./TimelineMessageList";
 import { useLoadOlderOnScroll } from "./useLoadOlderOnScroll";
@@ -23,8 +24,8 @@ type MessageTimelineProps = {
   channelType?: ChannelType | null;
   messages: TimelineMessage[];
   directMessageIntro?: {
-    avatarUrl: string | null;
     displayName: string;
+    participants: DirectMessageIntroParticipant[];
   } | null;
   isLoading?: boolean;
   emptyTitle?: string;
@@ -88,6 +89,12 @@ type ChannelIntro = {
   icon?: React.ReactNode;
 };
 
+type DirectMessageIntroParticipant = {
+  avatarUrl: string | null;
+  displayName: string;
+  pubkey: string;
+};
+
 export const MessageTimeline = React.memo(function MessageTimeline({
   agentPubkeys,
   channelId,
@@ -229,12 +236,8 @@ export const MessageTimeline = React.memo(function MessageTimeline({
                 className="mb-0.5 mt-auto flex w-full flex-col items-start px-3 py-2 text-left"
                 data-testid="message-dm-intro"
               >
-                <ProfileAvatar
-                  avatarUrl={directMessageIntro.avatarUrl}
-                  className="h-[60px] w-[60px] text-base"
-                  iconClassName="h-6 w-6"
-                  label={directMessageIntro.displayName}
-                  testId="message-dm-intro-avatar"
+                <DirectMessageIntroAvatarStack
+                  participants={directMessageIntro.participants}
                 />
                 <p className="mt-4 max-w-full truncate text-xl font-semibold leading-7 tracking-tight text-foreground">
                   {directMessageIntro.displayName}
@@ -420,3 +423,55 @@ export const MessageTimeline = React.memo(function MessageTimeline({
     </TooltipProvider>
   );
 });
+
+function DirectMessageIntroAvatarStack({
+  participants,
+}: {
+  participants: DirectMessageIntroParticipant[];
+}) {
+  const { hiddenCount, visibleParticipants } =
+    getDmParticipantPreview(participants);
+  const stackItemCount = visibleParticipants.length + (hiddenCount > 0 ? 1 : 0);
+
+  return (
+    <div
+      aria-hidden="true"
+      className="flex shrink-0 items-center"
+      data-testid="message-dm-intro-avatar-stack"
+    >
+      {visibleParticipants.map((participant, index) => (
+        <div
+          className={index > 0 ? "-ml-5" : ""}
+          data-testid="message-dm-intro-avatar-stack-participant"
+          key={participant.pubkey}
+          style={{
+            zIndex: index + 1,
+            ...(index < stackItemCount - 1 && {
+              mask: "radial-gradient(circle 34px at calc(100% + 10px) 50%, transparent 99%, #fff 100%)",
+              WebkitMask:
+                "radial-gradient(circle 34px at calc(100% + 10px) 50%, transparent 99%, #fff 100%)",
+            }),
+          }}
+        >
+          <UserAvatar
+            avatarUrl={participant.avatarUrl}
+            className="h-[60px] w-[60px] text-base"
+            displayName={participant.displayName}
+            size="md"
+          />
+        </div>
+      ))}
+      {hiddenCount > 0 ? (
+        <div
+          className={visibleParticipants.length > 0 ? "-ml-5" : ""}
+          data-testid="message-dm-intro-avatar-stack-more"
+          style={{ zIndex: stackItemCount }}
+        >
+          <span className="flex h-[60px] w-[60px] items-center justify-center rounded-full bg-secondary font-semibold text-secondary-foreground shadow-xs">
+            <span className="text-lg leading-none">+{hiddenCount}</span>
+          </span>
+        </div>
+      ) : null}
+    </div>
+  );
+}
diff --git a/desktop/src/features/messages/ui/TimelineMessageList.tsx b/desktop/src/features/messages/ui/TimelineMessageList.tsx
index a649fa357..a298d7e33 100644
--- a/desktop/src/features/messages/ui/TimelineMessageList.tsx
+++ b/desktop/src/features/messages/ui/TimelineMessageList.tsx
@@ -265,12 +265,14 @@ export const TimelineMessageList = React.memo(function TimelineMessageList({
                 : undefined
             }
             profiles={profiles}
+            showDepthGuides={false}
             videoReviewContext={videoReviewContextById.get(message.id)}
           />
           <MessageThreadSummaryRow
             depth={message.depth}
             message={message}
             onOpenThread={onReply}
+            showDepthGuides={false}
             summary={summary}
           />
           {footer}
@@ -303,6 +305,7 @@ export const TimelineMessageList = React.memo(function TimelineMessageList({
             onReply={onReply}
             profiles={profiles}
             searchQuery={isSearchMatch ? searchQuery : undefined}
+            showDepthGuides={false}
             videoReviewContext={videoReviewContextById.get(message.id)}
           />
           {footer}
diff --git a/desktop/src/features/sidebar/lib/channelLabels.ts b/desktop/src/features/sidebar/lib/channelLabels.ts
index 893e4f318..8408c34d8 100644
--- a/desktop/src/features/sidebar/lib/channelLabels.ts
+++ b/desktop/src/features/sidebar/lib/channelLabels.ts
@@ -2,6 +2,7 @@ import {
   resolveUserLabel,
   type UserProfileLookup,
 } from "@/features/profile/lib/identity";
+import { formatDmParticipantDisplayName } from "@/features/channels/lib/dmParticipantDisplay";
 import type { Channel } from "@/shared/api/types";
 
 function isGenericDmChannelName(name: string) {
@@ -46,5 +47,9 @@ export function resolveChannelDisplayLabel(
   );
   const uniqueLabels = [...new Set(resolvedLabels)];
 
-  return uniqueLabels.length > 0 ? uniqueLabels.join(", ") : channel.name;
+  return uniqueLabels.length > 0
+    ? formatDmParticipantDisplayName(
+        uniqueLabels.map((displayName) => ({ displayName })),
+      )
+    : channel.name;
 }
diff --git a/desktop/src/features/sidebar/ui/AppSidebar.tsx b/desktop/src/features/sidebar/ui/AppSidebar.tsx
index 00e8af524..458d36836 100644
--- a/desktop/src/features/sidebar/ui/AppSidebar.tsx
+++ b/desktop/src/features/sidebar/ui/AppSidebar.tsx
@@ -6,7 +6,7 @@ import {
   Bot,
   FolderGit2,
   Home,
-  PenSquare,
+  MessageCirclePlus,
   Zap,
 } from "lucide-react";
 import { useReconnectRelay } from "@/shared/api/useReconnectRelay";
@@ -43,7 +43,7 @@ import {
 import { CreateChannelDialog } from "@/features/sidebar/ui/CreateChannelDialog";
 import { NewDirectMessageDialog } from "@/features/sidebar/ui/NewDirectMessageDialog";
 import { SidebarProfileCard } from "@/features/sidebar/ui/SidebarProfileCard";
-import { SECTION_ACTION_VISIBILITY_CLASS } from "@/features/sidebar/ui/sidebarSectionStyles";
+import { SECTION_ICON_BUTTON_CLASS } from "@/features/sidebar/ui/sidebarSectionStyles";
 import type {
   Channel,
   ChannelVisibility,
@@ -51,13 +51,11 @@ import type {
   Profile,
   UserStatus,
 } from "@/shared/api/types";
-import { cn } from "@/shared/lib/cn";
 import {
   Sidebar,
   SidebarContent,
   SidebarFooter,
   SidebarGroup,
-  SidebarGroupAction,
   SidebarGroupContent,
   SidebarGroupLabel,
   SidebarHeader,
@@ -492,10 +490,10 @@ export function AppSidebar({
             </SidebarMenuButton>
             {shouldShowAgentCount ? (
               <SidebarMenuBadge
-                className="right-2 rounded-full bg-sidebar-accent/70 px-1.5 text-[11px] text-sidebar-foreground/75 peer-data-[active=true]/menu-button:bg-sidebar-active-foreground/20 peer-data-[active=true]/menu-button:text-sidebar-active-foreground"
+                className="right-2 rounded-full bg-sidebar-accent/70 px-1.5 text-[11px] leading-none text-sidebar-foreground/75 peer-data-[active=true]/menu-button:bg-sidebar-active-foreground/20 peer-data-[active=true]/menu-button:text-sidebar-active-foreground"
                 data-testid="sidebar-agents-count"
               >
-                {totalAgentCount}
+                <span className="leading-none">{totalAgentCount}</span>
               </SidebarMenuBadge>
             ) : null}
           </SidebarMenuItem>
@@ -688,21 +686,21 @@ export function AppSidebar({
               </FeatureGate>
               <SidebarSection
                 action={
-                  <SidebarGroupAction
-                    aria-expanded={isNewDmOpen}
-                    aria-label="Start a direct message"
-                    className={cn(
-                      "top-1/2 -translate-y-1/2 text-sidebar-foreground/50 hover:bg-sidebar-border/35 hover:text-sidebar-foreground",
-                      SECTION_ACTION_VISIBILITY_CLASS,
-                    )}
-                    data-testid="new-dm-trigger"
-                    onClick={() => {
-                      setIsNewDmOpen(true);
-                    }}
-                    type="button"
-                  >
-                    <PenSquare className="transition-transform" />
-                  </SidebarGroupAction>
+                  <div className="absolute right-1 top-1/2 z-10 flex -translate-y-1/2 items-center gap-0.5">
+                    <button
+                      aria-expanded={isNewDmOpen}
+                      aria-label="Compose new message"
+                      className={SECTION_ICON_BUTTON_CLASS}
+                      data-testid="new-dm-trigger"
+                      onClick={() => {
+                        setIsNewDmOpen(true);
+                      }}
+                      title="Compose new message"
+                      type="button"
+                    >
+                      <MessageCirclePlus className="h-4 w-4" />
+                    </button>
+                  </div>
                 }
                 dmParticipantsByChannelId={dmParticipantsByChannelId}
                 isCollapsed={collapsedGroups.directMessages}
diff --git a/desktop/src/features/sidebar/ui/NewDirectMessageDialog.tsx b/desktop/src/features/sidebar/ui/NewDirectMessageDialog.tsx
index 70b34d6a3..2a90dc51d 100644
--- a/desktop/src/features/sidebar/ui/NewDirectMessageDialog.tsx
+++ b/desktop/src/features/sidebar/ui/NewDirectMessageDialog.tsx
@@ -1,20 +1,38 @@
-import { Search, X } from "lucide-react";
+import { Bot, Search, X } from "lucide-react";
 import * as React from "react";
 
+import {
+  useManagedAgentsQuery,
+  useRelayAgentsQuery,
+} from "@/features/agents/hooks";
 import { useIsArchivedPredicate } from "@/features/identity-archive/hooks";
 import { useUserSearchQuery } from "@/features/profile/hooks";
 import { truncatePubkey } from "@/features/profile/lib/identity";
 import { ProfileAvatar } from "@/features/profile/ui/ProfileAvatar";
 import type { UserSearchResult } from "@/shared/api/types";
+import { normalizePubkey } from "@/shared/lib/pubkey";
 import { Button } from "@/shared/ui/button";
 import {
   Dialog,
+  DialogClose,
   DialogContent,
-  DialogDescription,
   DialogHeader,
   DialogTitle,
 } from "@/shared/ui/dialog";
-import { Input } from "@/shared/ui/input";
+
+const NEW_DM_SEARCH_SHELL_CLASS =
+  "group/search mt-4 flex cursor-text items-center gap-3 rounded-xl border border-input bg-background px-3 py-2.5 transition-colors duration-150 ease-out hover:border-muted-foreground/40 hover:bg-muted/70 focus-within:border-muted-foreground/50 focus-within:bg-muted/70";
+const NEW_DM_SEARCH_INPUT_CLASS =
+  "block h-6 min-w-0 flex-1 border-0 bg-transparent p-0 text-sm leading-5 text-muted-foreground/55 shadow-none caret-foreground outline-none transition-colors duration-150 ease-out placeholder:text-muted-foreground/55 group-hover/search:text-muted-foreground group-hover/search:placeholder:text-muted-foreground group-focus-within/search:text-foreground group-focus-within/search:placeholder:text-foreground";
+const DIRECT_MESSAGE_RECIPIENT_LIMIT = 50;
+const BUTTON_LABEL_MORPH_DURATION_MS = 220;
+const BUTTON_LABEL_MORPH_EASE = "cubic-bezier(0.23, 1, 0.32, 1)";
+const BUTTON_LABEL_FADE_MS = Math.min(
+  BUTTON_LABEL_MORPH_DURATION_MS * 0.5,
+  150,
+);
+const BUTTON_LABEL_EXIT_ATTR = "data-button-label-exiting";
+const BUTTON_LABEL_CURRENT_ATTR = "data-button-label-current";
 
 function formatUserName(user: UserSearchResult) {
   return (
@@ -24,15 +42,213 @@ function formatUserName(user: UserSearchResult) {
   );
 }
 
-function formatUserSecondary(user: UserSearchResult) {
-  const displayName = user.displayName?.trim();
-  const nip05Handle = user.nip05Handle?.trim();
+function scoreRecipientMatch(user: UserSearchResult, query: string) {
+  if (query.length === 0) {
+    return 0;
+  }
+
+  const labels = [
+    formatUserName(user),
+    user.nip05Handle?.trim() ?? "",
+    user.isAgent ? "agent" : "",
+  ];
 
-  if (displayName && nip05Handle) {
-    return nip05Handle;
+  for (const label of labels) {
+    const lower = label.toLowerCase();
+    if (lower.startsWith(query)) return 0;
+    if (lower.split(/[\s\-_]+/).some((word) => word.startsWith(query))) {
+      return 1;
+    }
+    if (lower.includes(query)) return 2;
   }
 
-  return truncatePubkey(user.pubkey);
+  const pubkey = normalizePubkey(user.pubkey);
+  if (pubkey.startsWith(query)) return 3;
+  if (pubkey.includes(query)) return 4;
+
+  return null;
+}
+
+function prefersReducedMotion() {
+  return (
+    typeof window !== "undefined" &&
+    window.matchMedia("(prefers-reduced-motion: reduce)").matches
+  );
+}
+
+function createButtonLabelSpan(text: string) {
+  const span = document.createElement("span");
+  span.setAttribute(BUTTON_LABEL_CURRENT_ATTR, "");
+  span.textContent = text;
+  span.style.display = "inline-block";
+  span.style.willChange = "opacity, transform";
+  return span;
+}
+
+function clearButtonLabelRoot(root: HTMLElement, text: string) {
+  root.replaceChildren(createButtonLabelSpan(text));
+  root.style.width = "auto";
+  root.style.height = "auto";
+}
+
+function MorphingButtonLabel({ text }: { text: string }) {
+  const rootRef = React.useRef<HTMLSpanElement>(null);
+  const currentTextRef = React.useRef("");
+  const cleanupSizeTransitionRef = React.useRef<(() => void) | null>(null);
+
+  React.useLayoutEffect(() => {
+    const root = rootRef.current;
+    if (!root || text === currentTextRef.current) {
+      return;
+    }
+    const morphRoot = root;
+
+    cleanupSizeTransitionRef.current?.();
+    cleanupSizeTransitionRef.current = null;
+
+    if (!currentTextRef.current || prefersReducedMotion()) {
+      clearButtonLabelRoot(root, text);
+      currentTextRef.current = text;
+      return;
+    }
+
+    root.querySelectorAll(`[${BUTTON_LABEL_EXIT_ATTR}]`).forEach((element) => {
+      element.remove();
+    });
+
+    const oldRect = root.getBoundingClientRect();
+    const oldWidth = oldRect.width;
+    const oldHeight = oldRect.height;
+    const rootRect = root.getBoundingClientRect();
+    const currentChild = root.querySelector<HTMLElement>(
+      `[${BUTTON_LABEL_CURRENT_ATTR}]`,
+    );
+
+    if (!currentChild || oldWidth === 0 || oldHeight === 0) {
+      clearButtonLabelRoot(root, text);
+      currentTextRef.current = text;
+      return;
+    }
+
+    const currentChildRect = currentChild.getBoundingClientRect();
+    const currentChildOpacity =
+      Number(getComputedStyle(currentChild).opacity) || 1;
+    currentChild.getAnimations().forEach((animation) => {
+      animation.cancel();
+    });
+    currentChild.removeAttribute(BUTTON_LABEL_CURRENT_ATTR);
+    currentChild.setAttribute(BUTTON_LABEL_EXIT_ATTR, "");
+    currentChild.style.position = "absolute";
+    currentChild.style.pointerEvents = "none";
+    currentChild.style.left = `${currentChildRect.left - rootRect.left}px`;
+    currentChild.style.top = `${currentChildRect.top - rootRect.top}px`;
+    currentChild.style.width = `${currentChildRect.width}px`;
+    currentChild.style.height = `${currentChildRect.height}px`;
+    currentChild.style.opacity = String(currentChildOpacity);
+
+    const nextChild = createButtonLabelSpan(text);
+    root.appendChild(nextChild);
+
+    root.style.width = "auto";
+    root.style.height = "auto";
+    void root.offsetWidth;
+
+    const nextRect = root.getBoundingClientRect();
+
+    root.style.width = `${oldWidth}px`;
+    root.style.height = `${oldHeight}px`;
+    void root.offsetWidth;
+
+    root.style.width = `${nextRect.width}px`;
+    root.style.height = `${nextRect.height}px`;
+
+    function cleanupSizeTransition() {
+      morphRoot.removeEventListener("transitionend", handleTransitionEnd);
+      window.clearTimeout(fallbackTimer);
+      cleanupSizeTransitionRef.current = null;
+      if (currentTextRef.current === text) {
+        morphRoot.style.width = "auto";
+        morphRoot.style.height = "auto";
+      }
+    }
+
+    function handleTransitionEnd(event: TransitionEvent) {
+      if (event.target !== morphRoot) {
+        return;
+      }
+      if (event.propertyName !== "width" && event.propertyName !== "height") {
+        return;
+      }
+      cleanupSizeTransition();
+    }
+
+    root.addEventListener("transitionend", handleTransitionEnd);
+    const fallbackTimer = window.setTimeout(
+      cleanupSizeTransition,
+      BUTTON_LABEL_MORPH_DURATION_MS + 50,
+    );
+    cleanupSizeTransitionRef.current = () => {
+      root.removeEventListener("transitionend", handleTransitionEnd);
+      window.clearTimeout(fallbackTimer);
+    };
+
+    currentChild.animate(
+      [{ transform: "none" }, { transform: "scale(0.95)" }],
+      {
+        duration: BUTTON_LABEL_MORPH_DURATION_MS,
+        easing: BUTTON_LABEL_MORPH_EASE,
+        fill: "both",
+      },
+    );
+    const exitFade = currentChild.animate(
+      [{ opacity: currentChildOpacity }, { opacity: 0 }],
+      {
+        duration: Math.min(BUTTON_LABEL_MORPH_DURATION_MS * 0.25, 150),
+        easing: "linear",
+        fill: "both",
+      },
+    );
+    exitFade.onfinish = () => currentChild.remove();
+
+    nextChild.animate([{ transform: "scale(0.95)" }, { transform: "none" }], {
+      duration: BUTTON_LABEL_MORPH_DURATION_MS,
+      easing: BUTTON_LABEL_MORPH_EASE,
+      fill: "both",
+    });
+    nextChild.animate([{ opacity: 0 }, { opacity: 1 }], {
+      delay: Math.min(BUTTON_LABEL_MORPH_DURATION_MS * 0.25, 150),
+      duration: BUTTON_LABEL_FADE_MS,
+      easing: "linear",
+      fill: "both",
+    });
+
+    currentTextRef.current = text;
+  }, [text]);
+
+  React.useEffect(() => {
+    return () => {
+      cleanupSizeTransitionRef.current?.();
+      rootRef.current?.getAnimations({ subtree: true }).forEach((animation) => {
+        animation.cancel();
+      });
+    };
+  }, []);
+
+  return (
+    <>
+      <span
+        aria-hidden="true"
+        className="relative inline-block whitespace-nowrap text-left align-middle leading-none will-change-[width,height]"
+        ref={rootRef}
+        style={{
+          transitionDuration: `${BUTTON_LABEL_MORPH_DURATION_MS}ms`,
+          transitionProperty: "width, height",
+          transitionTimingFunction: BUTTON_LABEL_MORPH_EASE,
+        }}
+      />
+      <span className="sr-only">{text}</span>
+    </>
+  );
 }
 
 export function NewDirectMessageDialog({
@@ -56,49 +272,181 @@ export function NewDirectMessageDialog({
     string | null
   >(null);
   const searchInputRef = React.useRef<HTMLInputElement>(null);
+  const selectedRecipientsRef = React.useRef<HTMLDivElement>(null);
+  const [selectedRecipientsHeight, setSelectedRecipientsHeight] =
+    React.useState(0);
   const deferredSearchQuery = React.useDeferredValue(searchQuery.trim());
+  const normalizedDeferredSearchQuery = deferredSearchQuery.toLowerCase();
   const hasReachedRecipientLimit = selectedUsers.length >= 8;
   const selectedPubkeys = React.useMemo(
-    () => new Set(selectedUsers.map((user) => user.pubkey.toLowerCase())),
+    () => new Set(selectedUsers.map((user) => normalizePubkey(user.pubkey))),
     [selectedUsers],
   );
+  const managedAgentsQuery = useManagedAgentsQuery({ enabled: open });
+  const relayAgentsQuery = useRelayAgentsQuery({ enabled: open });
   const userSearchQuery = useUserSearchQuery(deferredSearchQuery, {
-    enabled:
-      open && deferredSearchQuery.length > 0 && !hasReachedRecipientLimit,
-    limit: 8,
+    allowEmpty: true,
+    enabled: open && !hasReachedRecipientLimit,
+    limit: DIRECT_MESSAGE_RECIPIENT_LIMIT,
   });
   const isArchivedDiscovery = useIsArchivedPredicate();
-  const searchResults = React.useMemo(
-    () =>
-      (userSearchQuery.data ?? []).filter((user) => {
-        const normalizedPubkey = user.pubkey.toLowerCase();
-        return (
-          normalizedPubkey !== currentPubkey?.toLowerCase() &&
-          !selectedPubkeys.has(normalizedPubkey) &&
-          !isArchivedDiscovery(user.pubkey)
-        );
-      }),
-    [currentPubkey, isArchivedDiscovery, selectedPubkeys, userSearchQuery.data],
-  );
+  const searchResults = React.useMemo(() => {
+    const candidatesByPubkey = new Map<string, UserSearchResult>();
+    const currentPubkeyNormalized = currentPubkey
+      ? normalizePubkey(currentPubkey)
+      : null;
+    const eligibleAgentPubkeys = new Set([
+      ...(managedAgentsQuery.data ?? []).map((agent) =>
+        normalizePubkey(agent.pubkey),
+      ),
+      ...(relayAgentsQuery.data ?? [])
+        .filter((agent) => agent.respondTo === "anyone")
+        .map((agent) => normalizePubkey(agent.pubkey)),
+    ]);
+
+    const addCandidate = (candidate: UserSearchResult) => {
+      const pubkey = normalizePubkey(candidate.pubkey);
+
+      if (
+        pubkey === currentPubkeyNormalized ||
+        selectedPubkeys.has(pubkey) ||
+        isArchivedDiscovery(pubkey) ||
+        (candidate.isAgent && !eligibleAgentPubkeys.has(pubkey))
+      ) {
+        return;
+      }
+
+      const current = candidatesByPubkey.get(pubkey);
+      if (!current) {
+        candidatesByPubkey.set(pubkey, { ...candidate, pubkey });
+        return;
+      }
+
+      const candidateName = candidate.displayName?.trim() || null;
+      const currentName = current.displayName?.trim() || null;
+
+      candidatesByPubkey.set(pubkey, {
+        pubkey,
+        avatarUrl: current.avatarUrl ?? candidate.avatarUrl ?? null,
+        displayName:
+          candidate.isAgent && candidateName
+            ? candidateName
+            : current.isAgent
+              ? currentName
+              : (currentName ?? candidateName),
+        nip05Handle: current.nip05Handle ?? candidate.nip05Handle ?? null,
+        isAgent: current.isAgent || candidate.isAgent,
+      });
+    };
+
+    for (const user of userSearchQuery.data ?? []) {
+      addCandidate(user);
+    }
+
+    for (const agent of relayAgentsQuery.data ?? []) {
+      if (agent.respondTo !== "anyone") {
+        continue;
+      }
+
+      addCandidate({
+        pubkey: agent.pubkey,
+        displayName: agent.name,
+        avatarUrl: null,
+        nip05Handle: null,
+        isAgent: true,
+      });
+    }
+
+    for (const agent of managedAgentsQuery.data ?? []) {
+      addCandidate({
+        pubkey: agent.pubkey,
+        displayName: agent.name,
+        avatarUrl: null,
+        nip05Handle: null,
+        isAgent: true,
+      });
+    }
+
+    return [...candidatesByPubkey.values()]
+      .map((candidate, order) => ({
+        candidate,
+        order,
+        score: scoreRecipientMatch(candidate, normalizedDeferredSearchQuery),
+      }))
+      .filter(
+        (item): item is typeof item & { score: number } => item.score !== null,
+      )
+      .sort(
+        (left, right) =>
+          left.score - right.score ||
+          formatUserName(left.candidate).localeCompare(
+            formatUserName(right.candidate),
+          ) ||
+          left.order - right.order,
+      )
+      .slice(0, DIRECT_MESSAGE_RECIPIENT_LIMIT)
+      .map(({ candidate }) => candidate);
+  }, [
+    currentPubkey,
+    isArchivedDiscovery,
+    managedAgentsQuery.data,
+    normalizedDeferredSearchQuery,
+    relayAgentsQuery.data,
+    selectedPubkeys,
+    userSearchQuery.data,
+  ]);
+  const isDirectoryLoading =
+    userSearchQuery.isLoading ||
+    managedAgentsQuery.isLoading ||
+    relayAgentsQuery.isLoading;
 
   React.useEffect(() => {
     if (!open) {
       setSearchQuery("");
       setSelectedUsers([]);
       setSubmitErrorMessage(null);
+      setSelectedRecipientsHeight(0);
       return;
     }
 
     searchInputRef.current?.focus();
   }, [open]);
 
+  React.useEffect(() => {
+    const node = selectedRecipientsRef.current;
+    if (!node) {
+      setSelectedRecipientsHeight(0);
+      return;
+    }
+
+    const updateHeight = () => {
+      setSelectedRecipientsHeight(
+        selectedUsers.length > 0 ? node.scrollHeight : 0,
+      );
+    };
+
+    const animationFrame = window.requestAnimationFrame(updateHeight);
+    const resizeObserver = new ResizeObserver(updateHeight);
+    resizeObserver.observe(node);
+
+    return () => {
+      window.cancelAnimationFrame(animationFrame);
+      resizeObserver.disconnect();
+    };
+  }, [selectedUsers.length]);
+
   function handleSelectUser(user: UserSearchResult) {
     if (hasReachedRecipientLimit) {
       return;
     }
 
     setSelectedUsers((current) => {
-      if (current.some((candidate) => candidate.pubkey === user.pubkey)) {
+      const pubkey = normalizePubkey(user.pubkey);
+      if (
+        current.some(
+          (candidate) => normalizePubkey(candidate.pubkey) === pubkey,
+        )
+      ) {
         return current;
       }
 
@@ -110,17 +458,56 @@ export function NewDirectMessageDialog({
 
   return (
     <Dialog onOpenChange={onOpenChange} open={open}>
-      <DialogContent className="max-w-xl" data-testid="new-dm-dialog">
-        <DialogHeader>
-          <DialogTitle>New direct message</DialogTitle>
-          <DialogDescription>
-            Pick 1 to 8 people. If the conversation already exists, Buzz will
-            reopen it.
-          </DialogDescription>
+      <DialogContent
+        aria-describedby={undefined}
+        className="max-w-xl gap-0 overflow-hidden border-0 px-6 pb-0 pt-6"
+        data-testid="new-dm-dialog"
+        onOpenAutoFocus={(event) => {
+          event.preventDefault();
+          searchInputRef.current?.focus({ preventScroll: true });
+        }}
+        showCloseButton={false}
+      >
+        <DialogHeader className="space-y-0 pb-5">
+          <div className="flex items-center justify-between gap-4">
+            <DialogTitle>New direct message</DialogTitle>
+            <DialogClose className="flex h-8 w-8 shrink-0 items-center justify-center rounded-md text-muted-foreground transition-colors duration-150 ease-out hover:bg-accent hover:text-accent-foreground focus:outline-hidden focus:ring-1 focus:ring-ring">
+              <X className="h-4 w-4" />
+              <span className="sr-only">Close</span>
+            </DialogClose>
+          </div>
+          <label className={NEW_DM_SEARCH_SHELL_CLASS} htmlFor="new-dm-search">
+            <Search className="h-4 w-4 shrink-0 text-muted-foreground/55 transition-colors duration-150 ease-out group-hover/search:text-muted-foreground group-focus-within/search:text-foreground" />
+            <input
+              autoCapitalize="none"
+              autoCorrect="off"
+              className={NEW_DM_SEARCH_INPUT_CLASS}
+              data-testid="new-dm-search"
+              disabled={isPending}
+              id="new-dm-search"
+              onChange={(event) => {
+                setSearchQuery(event.target.value);
+                setSubmitErrorMessage(null);
+              }}
+              onKeyDown={(event) => {
+                if (event.key !== "Enter" || searchResults.length === 0) {
+                  return;
+                }
+
+                event.preventDefault();
+                handleSelectUser(searchResults[0]);
+              }}
+              placeholder="Search people and agents"
+              ref={searchInputRef}
+              spellCheck={false}
+              type="text"
+              value={searchQuery}
+            />
+          </label>
         </DialogHeader>
 
         <form
-          className="space-y-4"
+          className="flex flex-col"
           onSubmit={(event) => {
             event.preventDefault();
 
@@ -145,50 +532,23 @@ export function NewDirectMessageDialog({
               });
           }}
         >
-          <div className="overflow-hidden rounded-2xl border border-border/80 bg-muted/20">
-            <div className="flex items-center gap-2 px-3 py-2">
-              <Search className="h-4 w-4 text-muted-foreground" />
-              <Input
-                className="h-auto border-0 bg-transparent px-0 py-0 shadow-none focus-visible:ring-0"
-                data-testid="new-dm-search"
-                disabled={isPending}
-                onChange={(event) => {
-                  setSearchQuery(event.target.value);
-                  setSubmitErrorMessage(null);
-                }}
-                onKeyDown={(event) => {
-                  if (event.key !== "Enter" || searchResults.length === 0) {
-                    return;
-                  }
-
-                  event.preventDefault();
-                  handleSelectUser(searchResults[0]);
-                }}
-                placeholder="Search by name, NIP-05, or pubkey."
-                ref={searchInputRef}
-                value={searchQuery}
-              />
-            </div>
-
-            {selectedUsers.length > 0 ? (
-              <div className="flex flex-wrap gap-2 border-t border-border/70 px-3 py-2">
-                {selectedUsers.map((user) => (
-                  <div
-                    className="inline-flex items-center gap-2 rounded-full border border-border/80 bg-background/80 px-2.5 py-1 text-xs"
-                    data-testid={`new-dm-selected-${user.pubkey}`}
-                    key={user.pubkey}
-                  >
-                    <ProfileAvatar
-                      avatarUrl={user.avatarUrl}
-                      className="h-5 w-5 text-[10px] shadow-none"
-                      iconClassName="h-3 w-3"
-                      label={formatUserName(user)}
-                    />
-                    <span className="font-medium">{formatUserName(user)}</span>
+          <div
+            className="overflow-hidden transition-[height,opacity] duration-200 ease-[cubic-bezier(0.23,1,0.32,1)] motion-reduce:transition-none"
+            style={{
+              height: selectedRecipientsHeight,
+              opacity: selectedUsers.length > 0 ? 1 : 0,
+            }}
+          >
+            <div className="pb-4" ref={selectedRecipientsRef}>
+              {selectedUsers.length > 0 ? (
+                <div className="flex flex-wrap gap-2">
+                  {selectedUsers.map((user) => (
                     <button
                       aria-label={`Remove ${formatUserName(user)}`}
-                      className="text-muted-foreground transition-colors hover:text-foreground"
+                      className="group/selected-recipient inline-flex items-center gap-2 rounded-full border border-border/80 bg-background/80 py-1 pl-1 pr-3 text-xs transition-colors duration-150 ease-out hover:bg-muted/50 focus-visible:outline-hidden focus-visible:ring-1 focus-visible:ring-ring disabled:cursor-not-allowed disabled:opacity-60"
+                      data-testid={`new-dm-selected-${user.pubkey}`}
                       disabled={isPending}
+                      key={user.pubkey}
                       onClick={() => {
                         setSelectedUsers((current) =>
                           current.filter(
@@ -198,89 +558,151 @@ export function NewDirectMessageDialog({
                       }}
                       type="button"
                     >
-                      <X className="h-3.5 w-3.5" />
+                      <span className="relative h-8 w-8 shrink-0">
+                        <ProfileAvatar
+                          avatarUrl={user.avatarUrl}
+                          className="h-8 w-8 text-xs shadow-none transition-opacity duration-150 ease-out group-hover/selected-recipient:opacity-0 group-focus-visible/selected-recipient:opacity-0"
+                          iconClassName="h-4 w-4"
+                          label={formatUserName(user)}
+                        />
+                        <span className="absolute inset-0 flex items-center justify-center rounded-full bg-primary text-primary-foreground opacity-0 shadow transition-colors duration-150 ease-out group-hover/selected-recipient:bg-primary/90 group-hover/selected-recipient:opacity-100 group-focus-visible/selected-recipient:bg-primary/90 group-focus-visible/selected-recipient:opacity-100">
+                          <X aria-hidden="true" className="h-4 w-4" />
+                        </span>
+                      </span>
+                      <span className="font-medium">
+                        {formatUserName(user)}
+                      </span>
+                      {user.isAgent ? (
+                        <Bot
+                          aria-label="agent"
+                          className="h-3.5 w-3.5 text-muted-foreground"
+                        />
+                      ) : null}
                     </button>
-                  </div>
-                ))}
-              </div>
-            ) : null}
+                  ))}
+                </div>
+              ) : null}
+            </div>
+          </div>
 
-            <div className="border-t border-border/70 px-2 py-2">
-              {hasReachedRecipientLimit ? (
-                <p
-                  className="px-2 py-1 text-sm text-muted-foreground"
-                  data-testid="new-dm-limit"
-                >
-                  Direct messages support up to 9 people including you.
-                </p>
-              ) : deferredSearchQuery.length === 0 ? (
-                <p
-                  className="px-2 py-1 text-sm text-muted-foreground"
-                  data-testid="new-dm-empty"
-                >
-                  Search for someone to start a conversation.
-                </p>
-              ) : userSearchQuery.isLoading ? (
-                <p className="px-2 py-1 text-sm text-muted-foreground">
-                  Searching…
-                </p>
-              ) : searchResults.length > 0 ? (
-                <div className="space-y-1">
+          <div
+            className="overflow-hidden transition-[max-height,opacity] duration-200 ease-[cubic-bezier(0.23,1,0.32,1)] motion-reduce:transition-none"
+            style={{
+              maxHeight: hasReachedRecipientLimit ? 0 : "min(50vh, 24rem)",
+              opacity: hasReachedRecipientLimit ? 0 : 1,
+            }}
+          >
+            <div className="h-[min(50vh,24rem)] overflow-y-auto rounded-xl border border-border/70 bg-background/70">
+              {searchResults.length > 0 ? (
+                <div>
                   {searchResults.map((user) => (
-                    <button
-                      className="flex w-full items-center gap-3 rounded-xl px-3 py-2 text-left transition-colors hover:bg-accent hover:text-accent-foreground"
-                      data-testid={`new-dm-result-${user.pubkey}`}
+                    <div
+                      className="group/dm-result relative flex min-h-14 w-full items-center gap-3 px-4 py-3.5 text-left transition-colors duration-150 ease-out hover:bg-muted/40 focus-within:bg-muted/40"
                       key={user.pubkey}
-                      onClick={() => {
-                        handleSelectUser(user);
-                      }}
-                      type="button"
                     >
+                      <button
+                        aria-label={`Add ${formatUserName(user)}`}
+                        className="absolute inset-0 z-0 cursor-pointer focus-visible:outline-hidden focus-visible:ring-1 focus-visible:ring-ring"
+                        data-testid={`new-dm-result-${user.pubkey}`}
+                        disabled={isPending || hasReachedRecipientLimit}
+                        onClick={() => {
+                          handleSelectUser(user);
+                        }}
+                        type="button"
+                      />
                       <ProfileAvatar
                         avatarUrl={user.avatarUrl}
-                        className="h-9 w-9 text-xs shadow-none"
+                        className="pointer-events-none relative z-10 h-8 w-8 text-xs shadow-none"
                         iconClassName="h-4 w-4"
                         label={formatUserName(user)}
                       />
-                      <div className="min-w-0 flex-1">
-                        <p className="truncate text-sm font-medium">
-                          {formatUserName(user)}
-                        </p>
-                        <p className="truncate text-xs text-muted-foreground">
-                          {formatUserSecondary(user)}
-                        </p>
+                      <div className="pointer-events-none relative z-10 min-w-0 flex-1">
+                        {user.isAgent ? (
+                          <div className="relative min-w-0">
+                            <div className="flex min-w-0 items-center gap-2 transition-opacity duration-150 ease-out group-hover/dm-result:opacity-0 group-focus-within/dm-result:opacity-0">
+                              <span className="truncate text-sm font-medium tracking-tight">
+                                {formatUserName(user)}
+                              </span>
+                              <span className="inline-flex shrink-0 items-center gap-1 text-xs text-muted-foreground">
+                                <Bot
+                                  aria-hidden="true"
+                                  className="h-3 w-3"
+                                  data-testid="new-dm-agent-icon"
+                                />
+                                agent
+                              </span>
+                            </div>
+                            <span className="absolute inset-0 flex items-center opacity-0 transition-opacity duration-150 ease-out group-hover/dm-result:opacity-100 group-focus-within/dm-result:opacity-100">
+                              <span className="truncate font-mono text-sm text-muted-foreground">
+                                {truncatePubkey(user.pubkey)}
+                              </span>
+                            </span>
+                          </div>
+                        ) : (
+                          <span className="block truncate text-sm font-medium tracking-tight">
+                            {formatUserName(user)}
+                          </span>
+                        )}
                       </div>
-                      <span className="text-xs text-muted-foreground">Add</span>
-                    </button>
+                      <Button
+                        aria-label={`Add ${formatUserName(user)}`}
+                        className="relative z-20 shrink-0 opacity-0 transition-opacity duration-150 ease-out group-hover/dm-result:opacity-100 group-focus-within/dm-result:opacity-100"
+                        data-testid={`new-dm-add-${user.pubkey}`}
+                        disabled={isPending || hasReachedRecipientLimit}
+                        onClick={(event) => {
+                          event.stopPropagation();
+                          handleSelectUser(user);
+                        }}
+                        size="sm"
+                        type="button"
+                      >
+                        Add
+                      </Button>
+                    </div>
                   ))}
                 </div>
+              ) : isDirectoryLoading ? (
+                <p className="px-4 py-3 text-sm text-muted-foreground">
+                  {deferredSearchQuery.length === 0
+                    ? "Loading people and agents…"
+                    : "Searching…"}
+                </p>
               ) : (
-                <p className="px-2 py-1 text-sm text-muted-foreground">
-                  No matching users.
+                <p
+                  className="px-4 py-3 text-sm text-muted-foreground"
+                  data-testid="new-dm-empty"
+                >
+                  {deferredSearchQuery.length === 0
+                    ? "No people or agents available to message."
+                    : "No matching users."}
                 </p>
               )}
             </div>
           </div>
 
+          {hasReachedRecipientLimit ? (
+            <p
+              className="mt-4 text-sm text-destructive"
+              data-testid="new-dm-limit"
+            >
+              DMs support up to nine people, including you.
+            </p>
+          ) : null}
+
           {userSearchQuery.error instanceof Error ? (
-            <p className="text-sm text-destructive">
+            <p className="mt-4 text-sm text-destructive">
               {userSearchQuery.error.message}
             </p>
           ) : null}
 
           {submitErrorMessage ? (
-            <p className="text-sm text-destructive">{submitErrorMessage}</p>
+            <p className="mt-4 text-sm text-destructive">
+              {submitErrorMessage}
+            </p>
           ) : null}
 
-          <div className="flex items-center justify-between gap-3">
-            <p className="text-sm text-muted-foreground">
-              {selectedUsers.length === 0
-                ? "No recipients selected yet."
-                : `${selectedUsers.length} recipient${
-                    selectedUsers.length === 1 ? "" : "s"
-                  } selected.`}
-            </p>
-            <div className="flex items-center gap-2">
+          <div className="flex items-center gap-3 py-4">
+            <div className="ml-auto flex items-center gap-2">
               <Button
                 disabled={isPending}
                 onClick={() => onOpenChange(false)}
@@ -294,11 +716,15 @@ export function NewDirectMessageDialog({
                 disabled={isPending || selectedUsers.length === 0}
                 type="submit"
               >
-                {isPending
-                  ? "Opening..."
-                  : selectedUsers.length > 1
-                    ? "Start group DM"
-                    : "Message"}
+                <MorphingButtonLabel
+                  text={
+                    isPending
+                      ? "Opening..."
+                      : selectedUsers.length > 1
+                        ? "Start group DM"
+                        : "Message"
+                  }
+                />
               </Button>
             </div>
           </div>
diff --git a/desktop/src/features/sidebar/ui/SidebarSection.tsx b/desktop/src/features/sidebar/ui/SidebarSection.tsx
index 6d9210622..7e0ceb052 100644
--- a/desktop/src/features/sidebar/ui/SidebarSection.tsx
+++ b/desktop/src/features/sidebar/ui/SidebarSection.tsx
@@ -59,13 +59,26 @@ function DmChannelIcon({
   presenceStatus?: PresenceStatus;
 }) {
   const primaryParticipant = participants?.[0];
-  const secondaryParticipant = participants?.[1];
 
   if (!primaryParticipant) {
     return <CircleDot className="h-4 w-4" />;
   }
 
-  if (isPair || !secondaryParticipant) {
+  if (!isPair && participants && participants.length > 1) {
+    return (
+      <span
+        aria-hidden="true"
+        className="flex h-5 w-5 shrink-0 items-center justify-center rounded-full border border-sidebar-border/80 bg-sidebar-accent/80 text-[10px] font-semibold leading-none text-sidebar-foreground shadow-none"
+        data-testid={`channel-dm-count-${channelName}`}
+      >
+        <span className="translate-x-px leading-none">
+          {participants.length}
+        </span>
+      </span>
+    );
+  }
+
+  if (isPair || !participants || participants.length <= 1) {
     return (
       <span className="relative flex h-5 w-5 shrink-0 items-center justify-center">
         <ProfileAvatar
@@ -87,27 +100,7 @@ function DmChannelIcon({
     );
   }
 
-  return (
-    <span className="relative flex h-5 w-7 shrink-0 items-center">
-      <ProfileAvatar
-        avatarUrl={primaryParticipant.avatarUrl}
-        className="absolute left-0 top-0 h-[18px] w-[18px] rounded-full border-2 border-sidebar bg-sidebar-accent/80 text-[8px] text-sidebar-foreground shadow-none"
-        iconClassName="h-2.5 w-2.5"
-        label={primaryParticipant.label}
-      />
-      <ProfileAvatar
-        avatarUrl={secondaryParticipant.avatarUrl}
-        className="absolute bottom-0 right-0 h-[18px] w-[18px] rounded-full border-2 border-sidebar bg-sidebar-accent/80 text-[8px] text-sidebar-foreground shadow-none"
-        iconClassName="h-2.5 w-2.5"
-        label={secondaryParticipant.label}
-      />
-      {participants && participants.length > 2 ? (
-        <span className="absolute -bottom-1 -right-1 flex h-3.5 min-w-3.5 items-center justify-center rounded-full bg-sidebar-primary px-1 text-[8px] font-semibold text-sidebar-primary-foreground">
-          {participants.length}
-        </span>
-      ) : null}
-    </span>
-  );
+  return <CircleDot className="h-4 w-4" />;
 }
 
 function SidebarChannelIcon({
diff --git a/desktop/src/shared/styles/globals.css b/desktop/src/shared/styles/globals.css
index bb3fdb249..b9c785540 100644
--- a/desktop/src/shared/styles/globals.css
+++ b/desktop/src/shared/styles/globals.css
@@ -514,7 +514,7 @@
 .rich-text-composer .tiptap p.is-editor-empty:first-child::before {
   content: attr(data-placeholder);
   float: left;
-  color: hsl(var(--muted-foreground));
+  color: hsl(var(--muted-foreground) / 0.65);
   pointer-events: none;
   height: 0;
 }
diff --git a/desktop/src/shared/ui/dialog.tsx b/desktop/src/shared/ui/dialog.tsx
index a189d4af8..db304fffb 100644
--- a/desktop/src/shared/ui/dialog.tsx
+++ b/desktop/src/shared/ui/dialog.tsx
@@ -21,7 +21,7 @@ const DialogOverlay = React.forwardRef<
   return (
     <DialogPrimitive.Overlay
       className={cn(
-        "fixed inset-0 z-50 data-[state=open]:animate-in data-[state=closed]:animate-out data-[state=closed]:fade-out-0 data-[state=open]:fade-in-0",
+        "fixed inset-0 z-50 transition-none duration-200 ease-out data-[state=closed]:duration-150 data-[state=open]:animate-in data-[state=closed]:animate-out data-[state=closed]:fade-out-0 data-[state=open]:fade-in-0 motion-reduce:animate-none",
         isDark ? "bg-black/60" : "bg-black/10",
         className,
       )}
@@ -32,26 +32,34 @@ const DialogOverlay = React.forwardRef<
 });
 DialogOverlay.displayName = DialogPrimitive.Overlay.displayName;
 
+type DialogContentProps = React.ComponentPropsWithoutRef<
+  typeof DialogPrimitive.Content
+> & {
+  showCloseButton?: boolean;
+};
+
 const DialogContent = React.forwardRef<
   React.ElementRef<typeof DialogPrimitive.Content>,
-  React.ComponentPropsWithoutRef<typeof DialogPrimitive.Content>
->(({ className, children, ...props }, ref) => (
+  DialogContentProps
+>(({ className, children, showCloseButton = true, ...props }, ref) => (
   <DialogPortal>
     <DialogOverlay />
     <div className="fixed inset-0 z-50 grid place-items-center overflow-y-auto p-4 pointer-events-none">
       <DialogPrimitive.Content
         className={cn(
-          "pointer-events-auto relative grid w-[calc(100vw-2rem)] max-w-2xl gap-4 rounded-3xl border border-border bg-background p-6 shadow-2xl duration-200 data-[state=open]:animate-in data-[state=closed]:animate-out data-[state=closed]:fade-out-0 data-[state=open]:fade-in-0 data-[state=closed]:zoom-out-95 data-[state=open]:zoom-in-95",
+          "pointer-events-auto relative grid w-[calc(100vw-2rem)] max-w-2xl gap-4 rounded-3xl border border-border bg-background p-6 shadow-2xl transition-none duration-200 ease-out data-[state=closed]:duration-150 data-[state=open]:animate-in data-[state=closed]:animate-out data-[state=closed]:fade-out-0 data-[state=open]:fade-in-0 data-[state=closed]:zoom-out-95 data-[state=open]:zoom-in-95 motion-reduce:animate-none",
           className,
         )}
         ref={ref}
         {...props}
       >
         {children}
-        <DialogPrimitive.Close className="absolute right-4 top-4 rounded-md p-1 text-muted-foreground transition-colors hover:bg-accent hover:text-accent-foreground focus:outline-hidden focus:ring-1 focus:ring-ring">
-          <X className="h-4 w-4" />
-          <span className="sr-only">Close</span>
-        </DialogPrimitive.Close>
+        {showCloseButton ? (
+          <DialogPrimitive.Close className="absolute right-4 top-4 flex h-8 w-8 items-center justify-center rounded-md text-muted-foreground transition-colors duration-150 ease-out hover:bg-accent hover:text-accent-foreground focus:outline-hidden focus:ring-1 focus:ring-ring">
+            <X className="h-4 w-4" />
+            <span className="sr-only">Close</span>
+          </DialogPrimitive.Close>
+        ) : null}
       </DialogPrimitive.Content>
     </div>
   </DialogPortal>
@@ -74,7 +82,7 @@ const DialogTitle = React.forwardRef<
   React.ComponentPropsWithoutRef<typeof DialogPrimitive.Title>
 >(({ className, ...props }, ref) => (
   <DialogPrimitive.Title
-    className={cn("text-lg font-semibold tracking-tight", className)}
+    className={cn("text-xl font-semibold tracking-tight", className)}
     ref={ref}
     {...props}
   />
diff --git a/desktop/src/shared/ui/sidebar.tsx b/desktop/src/shared/ui/sidebar.tsx
index 00b465553..1b4e333cf 100644
--- a/desktop/src/shared/ui/sidebar.tsx
+++ b/desktop/src/shared/ui/sidebar.tsx
@@ -380,7 +380,7 @@ const Sidebar = React.forwardRef<
         >
           <div
             data-sidebar="sidebar"
-            className="flex h-full w-full flex-col bg-sidebar group-data-[variant=sidebar]:border-r group-data-[variant=sidebar]:border-sidebar-border group-data-[variant=sidebar]:pr-px group-data-[variant=floating]:rounded-lg group-data-[variant=floating]:border group-data-[variant=floating]:border-sidebar-border group-data-[variant=floating]:shadow"
+            className="flex h-full w-full flex-col bg-sidebar group-data-[variant=sidebar]:pr-px group-data-[variant=floating]:rounded-lg group-data-[variant=floating]:border group-data-[variant=floating]:border-sidebar-border group-data-[variant=floating]:shadow"
           >
             {children}
           </div>
@@ -577,7 +577,7 @@ const SidebarRail = React.forwardRef<
         className={cn(
           "absolute inset-y-0 z-20 hidden w-4 -translate-x-1/2 transition-all ease-linear group-data-[side=left]:-right-4 group-data-[side=right]:left-0 sm:flex",
           "cursor-col-resize",
-          "after:absolute after:inset-y-0 after:left-1/2 after:z-10 after:w-px after:-translate-x-1/2 after:bg-sidebar-border after:opacity-0 after:transition-opacity after:content-[''] hover:after:opacity-100 focus-visible:after:opacity-100 group-data-[resizing=true]:after:opacity-100",
+          "after:absolute after:inset-y-0 after:left-1/2 after:z-10 after:w-px after:-translate-x-1/2 after:bg-border/50 after:transition-colors after:content-[''] hover:after:bg-sidebar-border focus-visible:after:bg-sidebar-border group-data-[resizing=true]:after:bg-sidebar-border",
           "[[data-state=collapsed]_&]:cursor-pointer",
           "group-data-[collapsible=offcanvas]:translate-x-0 group-data-[collapsible=offcanvas]:hover:bg-sidebar",
           "[[data-side=left][data-collapsible=offcanvas]_&]:-right-2",
diff --git a/desktop/tests/e2e/channels.spec.ts b/desktop/tests/e2e/channels.spec.ts
index 654986b5f..96bb6b8ac 100644
--- a/desktop/tests/e2e/channels.spec.ts
+++ b/desktop/tests/e2e/channels.spec.ts
@@ -361,6 +361,18 @@ test("start a new direct message from the sidebar", async ({ page }) => {
   await expect(
     page.getByTestId(`new-dm-selected-${TEST_IDENTITIES.charlie.pubkey}`),
   ).toBeVisible();
+  await page
+    .getByTestId(`new-dm-selected-${TEST_IDENTITIES.charlie.pubkey}`)
+    .click();
+  await expect(
+    page.getByTestId(`new-dm-selected-${TEST_IDENTITIES.charlie.pubkey}`),
+  ).not.toBeVisible();
+  await page
+    .getByTestId(`new-dm-result-${TEST_IDENTITIES.charlie.pubkey}`)
+    .click();
+  await expect(
+    page.getByTestId(`new-dm-selected-${TEST_IDENTITIES.charlie.pubkey}`),
+  ).toBeVisible();
 
   await page.getByTestId("new-dm-submit").click();
 
@@ -368,6 +380,90 @@ test("start a new direct message from the sidebar", async ({ page }) => {
   await expect(page.getByTestId("chat-title")).toHaveText("charlie");
 });
 
+test("shows capped participant stack in group direct message header", async ({
+  page,
+}) => {
+  await page.goto("/");
+
+  await page.getByTestId("new-dm-trigger").click();
+  await expect(page.getByTestId("new-dm-dialog")).toBeVisible();
+
+  for (const identity of [
+    TEST_IDENTITIES.alice,
+    TEST_IDENTITIES.bob,
+    TEST_IDENTITIES.charlie,
+    TEST_IDENTITIES.outsider,
+  ]) {
+    await page.getByTestId("new-dm-search").fill(identity.username);
+    await page.getByTestId(`new-dm-result-${identity.pubkey}`).click();
+  }
+
+  await page.getByTestId("new-dm-submit").click();
+
+  await expect(page.getByTestId("channel-dm-count-Group DM (5)")).toHaveText(
+    "4",
+  );
+  await expect(page.getByTestId("chat-title")).toContainText("alice");
+  await expect(page.getByTestId("chat-title")).toContainText("bob");
+  await expect(page.getByTestId("chat-title")).toContainText("charlie");
+  await expect(page.getByTestId("chat-title")).toContainText("+1 more");
+  await expect(page.getByTestId("chat-title")).not.toContainText("outsider");
+  const chatTitle = await page.getByTestId("chat-title").innerText();
+  await expect(
+    page.getByTestId("message-input").locator("[data-placeholder]").first(),
+  ).toHaveAttribute("data-placeholder", `Message ${chatTitle}`);
+  const composerColors = await page
+    .getByTestId("message-input")
+    .evaluate((element) => {
+      const placeholderElement =
+        element.querySelector<HTMLElement>("[data-placeholder]");
+      if (!placeholderElement) {
+        return null;
+      }
+
+      return {
+        placeholderColor: window.getComputedStyle(
+          placeholderElement,
+          "::before",
+        ).color,
+        textColor: window.getComputedStyle(element).color,
+      };
+    });
+  expect(composerColors).not.toBeNull();
+  expect(composerColors?.placeholderColor).not.toBe(composerColors?.textColor);
+  await expect(page.getByTestId("chat-header-dm-avatar")).toHaveCount(0);
+  await expect(page.getByTestId("chat-header-dm-avatar-stack")).toBeVisible();
+  await expect(
+    page.getByTestId("chat-header-dm-avatar-stack-participant"),
+  ).toHaveCount(3);
+  await expect(page.getByTestId("chat-header-dm-avatar-stack-more")).toHaveText(
+    "+1",
+  );
+  const headerStackBox = await page
+    .getByTestId("chat-header-dm-avatar-stack")
+    .boundingBox();
+  const headerTitleBox = await page.getByTestId("chat-title").boundingBox();
+  expect(headerStackBox).not.toBeNull();
+  expect(headerTitleBox).not.toBeNull();
+  expect((headerStackBox?.x ?? 0) + (headerStackBox?.width ?? 0)).toBeLessThan(
+    headerTitleBox?.x ?? 0,
+  );
+  await expect(page.getByTestId("message-dm-intro")).toContainText("alice");
+  await expect(page.getByTestId("message-dm-intro")).toContainText("bob");
+  await expect(page.getByTestId("message-dm-intro")).toContainText("charlie");
+  await expect(page.getByTestId("message-dm-intro")).toContainText("+1 more");
+  await expect(page.getByTestId("message-dm-intro")).not.toContainText(
+    "outsider",
+  );
+  await expect(page.getByTestId("message-dm-intro-avatar-stack")).toBeVisible();
+  await expect(
+    page.getByTestId("message-dm-intro-avatar-stack-participant"),
+  ).toHaveCount(3);
+  await expect(
+    page.getByTestId("message-dm-intro-avatar-stack-more"),
+  ).toHaveText("+1");
+});
+
 test("create stream with name and description", async ({ page }) => {
   const channelName = `my-new-stream-${Date.now()}`;
 
@@ -1061,6 +1157,14 @@ test("members sidebar can invite and remove members", async ({ page }) => {
     0,
   );
 
+  await expect(page.getByText(/Members · \d+/)).toBeVisible();
+  await page.getByTestId("channel-management-search-users").fill("a");
+  await expect(page.getByText("Members", { exact: true })).toBeVisible();
+  await expect(page.getByText(/Members · \d+/)).toHaveCount(0);
+  await expect(
+    page.getByText("Not in this channel", { exact: true }),
+  ).toBeVisible();
+
   await page.getByTestId("channel-management-search-users").fill("char");
   await expect(
     page.getByTestId(
@@ -1071,21 +1175,17 @@ test("members sidebar can invite and remove members", async ({ page }) => {
     .getByTestId(`channel-user-search-result-${TEST_IDENTITIES.charlie.pubkey}`)
     .click();
   await expect(
-    page.getByTestId(`selected-invitee-${TEST_IDENTITIES.charlie.pubkey}`),
+    page.getByTestId(`sidebar-member-${TEST_IDENTITIES.charlie.pubkey}`),
   ).toContainText("charlie");
-
-  await page.getByTestId("channel-management-add-role").selectOption("admin");
-  await page.getByTestId("channel-management-add-members").click();
-
   await expect(
     page.getByTestId(`selected-invitee-${TEST_IDENTITIES.charlie.pubkey}`),
   ).toHaveCount(0);
+  await expect(page.getByTestId("channel-management-add-members")).toHaveCount(
+    0,
+  );
   await expect(page.getByTestId("channel-management-search-users")).toHaveValue(
-    "",
+    "char",
   );
-  await expect(
-    page.getByTestId(`sidebar-member-${TEST_IDENTITIES.charlie.pubkey}`),
-  ).toContainText("charlie");
   await expectMembersTriggerCount(page, initialMemberCount + 1);
 
   await openMemberMenu(page, TEST_IDENTITIES.charlie.pubkey);
@@ -1099,31 +1199,19 @@ test("members sidebar can invite and remove members", async ({ page }) => {
   await expectMembersTriggerCount(page, initialMemberCount);
 });
 
-test("members sidebar keeps direct pubkey entry behind a toggle", async ({
-  page,
-}) => {
+test("members modal does not show direct pubkey entry", async ({ page }) => {
   await page.goto("/");
   await openMembersSidebar(page, "general");
-  const initialMemberCount = await readMembersTriggerCount(page);
 
   await expect(page.getByTestId("channel-management-add-pubkeys")).toHaveCount(
     0,
   );
-
-  await page.getByTestId("channel-management-toggle-direct-pubkeys").click();
   await expect(
-    page.getByTestId("channel-management-add-pubkeys"),
-  ).toBeVisible();
-
-  await page
-    .getByTestId("channel-management-add-pubkeys")
-    .fill(TEST_IDENTITIES.outsider.pubkey);
-  await page.getByTestId("channel-management-add-members").click();
-
+    page.getByTestId("channel-management-toggle-direct-pubkeys"),
+  ).toHaveCount(0);
   await expect(
-    page.getByTestId(`sidebar-member-${TEST_IDENTITIES.outsider.pubkey}`),
-  ).toContainText("outsider");
-  await expectMembersTriggerCount(page, initialMemberCount + 1);
+    page.getByTestId("channel-management-search-users"),
+  ).toHaveAttribute("placeholder", "Add people and agents");
 });
 
 test("open-channel members can add agents from the header", async ({
@@ -1172,19 +1260,21 @@ test("private-channel members can add members and bots without admin", async ({
   await expect(
     page.getByTestId("channel-management-search-users"),
   ).toBeVisible();
+  await page.getByTestId("channel-management-search-users").fill("char");
+  await page
+    .getByTestId(`channel-user-search-result-${TEST_IDENTITIES.charlie.pubkey}`)
+    .click();
   await expect(
-    page.getByTestId("channel-management-add-members"),
-  ).toBeVisible();
+    page.getByTestId(`sidebar-member-${TEST_IDENTITIES.charlie.pubkey}`),
+  ).toContainText("charlie");
 
-  // The role dropdown hides the elevated "admin" option for non-admins — the
-  // relay rejects it anyway — while keeping the non-elevated roles a member
-  // may grant (member, guest, bot).
-  const roleSelect = page.getByTestId("channel-management-add-role");
-  await expect(roleSelect.locator("option")).toHaveText([
-    "member",
-    "guest",
-    "bot",
-  ]);
+  // The modal no longer exposes member/guest/bot role choices or a staged
+  // submit button; selected people are added immediately as members and
+  // selected agents are added as bots.
+  await expect(page.getByTestId("channel-management-add-role")).toHaveCount(0);
+  await expect(page.getByTestId("channel-management-add-members")).toHaveCount(
+    0,
+  );
 });
 
 test("removing a channel-scoped agent preserves the managed agent record", async ({
diff --git a/desktop/tests/e2e/messaging.spec.ts b/desktop/tests/e2e/messaging.spec.ts
index 610f174e0..0a3ecf847 100644
--- a/desktop/tests/e2e/messaging.spec.ts
+++ b/desktop/tests/e2e/messaging.spec.ts
@@ -626,6 +626,17 @@ test("opens a single-level thread panel with inline expansion", async ({
   await expect(
     rootSummaryRow.getByTestId("message-thread-summary-participant"),
   ).toHaveCount(2);
+  await expect
+    .poll(() =>
+      rootSummaryRow
+        .getByTestId("message-thread-summary-participant")
+        .evaluateAll((participants) =>
+          participants
+            .map((participant) => getComputedStyle(participant).zIndex)
+            .join(","),
+        ),
+    )
+    .toBe("1,2");
 
   await expect
     .poll(async () => {

From 7ddfba22c2ebff8368064c975162144ff7a5cc2f Mon Sep 17 00:00:00 2001
From: klopez4212 <klopez4212@gmail.com>
Date: Mon, 15 Jun 2026 14:40:46 +0100
Subject: [PATCH 2/6] Trigger CI


From 258844fb4ce69f41a3395d7f765d2b9c06549055 Mon Sep 17 00:00:00 2001
From: klopez4212 <klopez4212@gmail.com>
Date: Mon, 15 Jun 2026 15:07:56 +0100
Subject: [PATCH 3/6] Fix desktop modal CI failures

---
 .../channels/ui/ChannelScreenHeader.tsx         |  2 +-
 desktop/tests/e2e/agents.spec.ts                |  5 ++++-
 desktop/tests/e2e/channels.spec.ts              |  1 +
 desktop/tests/e2e/identity-archive-hide.spec.ts | 16 +++++++---------
 desktop/tests/e2e/mesh-compute.spec.ts          | 17 ++++++++++++-----
 desktop/tests/e2e/persona-env-vars.spec.ts      |  5 ++++-
 desktop/tests/e2e/smoke.spec.ts                 |  5 ++++-
 7 files changed, 33 insertions(+), 18 deletions(-)

diff --git a/desktop/src/features/channels/ui/ChannelScreenHeader.tsx b/desktop/src/features/channels/ui/ChannelScreenHeader.tsx
index 83d551259..81dc77206 100644
--- a/desktop/src/features/channels/ui/ChannelScreenHeader.tsx
+++ b/desktop/src/features/channels/ui/ChannelScreenHeader.tsx
@@ -117,7 +117,7 @@ export function ChannelScreenHeader({
         <ChannelHeaderStatusBadge
           channelType={activeChannel?.channelType}
           ephemeralDisplay={activeChannelEphemeralDisplay}
-          presenceStatus={activeDmPresenceStatus}
+          presenceStatus={isGroupDm ? null : activeDmPresenceStatus}
         />
       }
       title={activeChannelTitle}
diff --git a/desktop/tests/e2e/agents.spec.ts b/desktop/tests/e2e/agents.spec.ts
index 047d40bc8..2ba44e96f 100644
--- a/desktop/tests/e2e/agents.spec.ts
+++ b/desktop/tests/e2e/agents.spec.ts
@@ -30,7 +30,10 @@ async function gotoApp(page: import("@playwright/test").Page) {
 }
 
 async function openPersonaCatalog(page: import("@playwright/test").Page) {
-  await page.getByRole("button", { name: "New" }).click();
+  await page
+    .getByTestId("agents-library-personas")
+    .getByRole("button", { name: "New", exact: true })
+    .click();
   await page.getByText("Choose from Catalog...").click();
 }
 
diff --git a/desktop/tests/e2e/channels.spec.ts b/desktop/tests/e2e/channels.spec.ts
index 96bb6b8ac..e4d541771 100644
--- a/desktop/tests/e2e/channels.spec.ts
+++ b/desktop/tests/e2e/channels.spec.ts
@@ -433,6 +433,7 @@ test("shows capped participant stack in group direct message header", async ({
   expect(composerColors?.placeholderColor).not.toBe(composerColors?.textColor);
   await expect(page.getByTestId("chat-header-dm-avatar")).toHaveCount(0);
   await expect(page.getByTestId("chat-header-dm-avatar-stack")).toBeVisible();
+  await expect(page.getByTestId("chat-presence-badge")).toHaveCount(0);
   await expect(
     page.getByTestId("chat-header-dm-avatar-stack-participant"),
   ).toHaveCount(3);
diff --git a/desktop/tests/e2e/identity-archive-hide.spec.ts b/desktop/tests/e2e/identity-archive-hide.spec.ts
index 4cfd3341c..d80c684b4 100644
--- a/desktop/tests/e2e/identity-archive-hide.spec.ts
+++ b/desktop/tests/e2e/identity-archive-hide.spec.ts
@@ -37,7 +37,7 @@ test.describe("NIP-IA hide archived from discovery", () => {
     // Folded Archived section is visible with count = 1.
     await expect(page.getByTestId("members-sidebar-archived")).toBeVisible();
     await expect(page.getByTestId("members-sidebar-archived-count")).toHaveText(
-      "1",
+      "(1)",
     );
 
     // Expanding it reveals Alice.
@@ -133,14 +133,12 @@ test.describe("NIP-IA hide archived from discovery", () => {
     await page.getByTestId("channel-members-trigger").click();
     await expect(page.getByTestId("members-sidebar")).toBeVisible();
 
-    // Self appears in active People list — NOT folded into Archived. The
-    // members sidebar renders the current user as "You" + a pubkey-prefix.
-    await expect(page.getByTestId("members-sidebar-people")).toContainText(
-      "You",
-    );
-    await expect(page.getByTestId("members-sidebar-people")).toContainText(
-      "deadbeef",
-    );
+    // Self appears in active People list — NOT folded into Archived.
+    const peopleList = page.getByTestId("members-sidebar-people");
+    await expect(peopleList).toContainText("You");
+    await expect(
+      peopleList.getByTestId(`sidebar-member-${SELF_PUBKEY}`),
+    ).toBeVisible();
     // No Archived section at all when self is the only archived pubkey in
     // the channel (self-exemption makes archived.length === 0).
     await expect(page.getByTestId("members-sidebar-archived")).toHaveCount(0);
diff --git a/desktop/tests/e2e/mesh-compute.spec.ts b/desktop/tests/e2e/mesh-compute.spec.ts
index e80c4b84a..6d3f8ad96 100644
--- a/desktop/tests/e2e/mesh-compute.spec.ts
+++ b/desktop/tests/e2e/mesh-compute.spec.ts
@@ -75,6 +75,13 @@ async function openManagedAgentActions(
   await expect(trigger).toHaveAttribute("data-state", "open");
 }
 
+async function openNewAgentMenu(page: import("@playwright/test").Page) {
+  await page
+    .getByTestId("agents-library-personas")
+    .getByRole("button", { name: "New", exact: true })
+    .click();
+}
+
 test.beforeEach(async ({ page }) => {
   await installMockBridge(page);
 });
@@ -140,7 +147,7 @@ test("Run-on-relay-mesh ensures the client node BEFORE spawning the agent", asyn
 }) => {
   await gotoApp(page);
   await page.getByTestId("open-agents-view").click();
-  await page.getByRole("button", { name: "New" }).click();
+  await openNewAgentMenu(page);
   await page.getByText("Custom Agent").click();
 
   // Member is admitted -> the relay-mesh toggle becomes enabled (availability
@@ -184,7 +191,7 @@ test("Run-on-relay-mesh skips connect signaling for own serve target", async ({
 }) => {
   await gotoApp(page);
   await page.getByTestId("open-agents-view").click();
-  await page.getByRole("button", { name: "New" }).click();
+  await openNewAgentMenu(page);
   await page.getByText("Custom Agent").click();
   await page.getByTestId("agent-name-input").fill("Own Mesh Agent");
 
@@ -224,7 +231,7 @@ test("Run-on-relay-mesh canonicalizes the mesh connect #p target", async ({
   });
   await gotoApp(page);
   await page.getByTestId("open-agents-view").click();
-  await page.getByRole("button", { name: "New" }).click();
+  await openNewAgentMenu(page);
   await page.getByText("Custom Agent").click();
   await page.getByTestId("agent-name-input").fill("Mesh Agent");
 
@@ -262,7 +269,7 @@ test("a non-member cannot enable relay-mesh — membership is the gate", async (
   await setMesh(page, { admitted: false, denyReason: "not a relay member" });
 
   await page.getByTestId("open-agents-view").click();
-  await page.getByRole("button", { name: "New" }).click();
+  await openNewAgentMenu(page);
   await page.getByText("Custom Agent").click();
 
   // The relay-mesh toggle stays disabled — a non-member cannot even opt into
@@ -281,7 +288,7 @@ test("saved relay-mesh agents restart via the backend serve-target preflight", a
 }) => {
   await gotoApp(page);
   await page.getByTestId("open-agents-view").click();
-  await page.getByRole("button", { name: "New" }).click();
+  await openNewAgentMenu(page);
   await page.getByText("Custom Agent").click();
   await page.getByTestId("agent-name-input").fill("Saved relay mesh agent");
 
diff --git a/desktop/tests/e2e/persona-env-vars.spec.ts b/desktop/tests/e2e/persona-env-vars.spec.ts
index eb9382e8a..842cc56c5 100644
--- a/desktop/tests/e2e/persona-env-vars.spec.ts
+++ b/desktop/tests/e2e/persona-env-vars.spec.ts
@@ -226,7 +226,10 @@ test("env vars editor renders in PersonaDialog new-persona form", async ({
 
   // Open the Agents view, click New > Persona to open the persona dialog.
   await page.getByTestId("open-agents-view").click();
-  await page.getByRole("button", { name: "New" }).click();
+  await page
+    .getByTestId("agents-library-personas")
+    .getByRole("button", { name: "New", exact: true })
+    .click();
   await page.getByRole("menuitem", { name: /^Persona$/ }).click();
 
   // The env vars editor should be present.
diff --git a/desktop/tests/e2e/smoke.spec.ts b/desktop/tests/e2e/smoke.spec.ts
index 85d2ccc6b..0e39569e7 100644
--- a/desktop/tests/e2e/smoke.spec.ts
+++ b/desktop/tests/e2e/smoke.spec.ts
@@ -116,7 +116,10 @@ test("create agent supports parallelism and system prompt overrides", async ({
 
   await page.goto("/");
   await page.getByTestId("open-agents-view").click();
-  await page.getByRole("button", { name: "New" }).click();
+  await page
+    .getByTestId("agents-library-personas")
+    .getByRole("button", { name: "New", exact: true })
+    .click();
   await page.getByText("Custom Agent").click();
 
   await page.getByTestId("agent-name-input").fill(agentName);

From addf73e34e59b30995ec461557e6562f21d34cf0 Mon Sep 17 00:00:00 2001
From: klopez4212 <klopez4212@gmail.com>
Date: Mon, 15 Jun 2026 21:44:39 +0100
Subject: [PATCH 4/6] Tolerate canceled screenshot animations

---
 desktop/tests/e2e/relay-connectivity-screenshots.spec.ts | 2 +-
 1 file changed, 1 insertion(+), 1 deletion(-)

diff --git a/desktop/tests/e2e/relay-connectivity-screenshots.spec.ts b/desktop/tests/e2e/relay-connectivity-screenshots.spec.ts
index 1525f92b7..b46cddef0 100644
--- a/desktop/tests/e2e/relay-connectivity-screenshots.spec.ts
+++ b/desktop/tests/e2e/relay-connectivity-screenshots.spec.ts
@@ -16,7 +16,7 @@ const SELF_PROFILE_CACHE_KEY = `buzz-self-profile.v1:${MOCK_RELAY_URL}:${MOCK_PU
 
 async function settle(page: import("@playwright/test").Page) {
   await page.evaluate(() =>
-    Promise.all(document.getAnimations().map((a) => a.finished)),
+    Promise.allSettled(document.getAnimations().map((a) => a.finished)),
   );
 }
 

From df2ee58e5de6e9ddcabd5774e75980b2f76ce635 Mon Sep 17 00:00:00 2001
From: klopez4212 <klopez4212@gmail.com>
Date: Mon, 15 Jun 2026 21:47:42 +0100
Subject: [PATCH 5/6] Address modal search review feedback

---
 .../features/channels/ui/MembersSidebar.tsx   |  65 ++-------
 .../profile/lib/userCandidateSearch.test.mjs  |  98 ++++++++++++++
 .../profile/lib/userCandidateSearch.ts        |  89 +++++++++++++
 .../sidebar/ui/NewDirectMessageDialog.tsx     | 125 +++++++-----------
 desktop/src/shared/ui/modalSearchStyles.ts    |   5 +
 desktop/tests/e2e/channels.spec.ts            |  19 ++-
 6 files changed, 267 insertions(+), 134 deletions(-)
 create mode 100644 desktop/src/features/profile/lib/userCandidateSearch.test.mjs
 create mode 100644 desktop/src/features/profile/lib/userCandidateSearch.ts
 create mode 100644 desktop/src/shared/ui/modalSearchStyles.ts

diff --git a/desktop/src/features/channels/ui/MembersSidebar.tsx b/desktop/src/features/channels/ui/MembersSidebar.tsx
index c309b37fe..9da4347b8 100644
--- a/desktop/src/features/channels/ui/MembersSidebar.tsx
+++ b/desktop/src/features/channels/ui/MembersSidebar.tsx
@@ -17,6 +17,7 @@ import {
   useUserSearchQuery,
   useUsersBatchQuery,
 } from "@/features/profile/hooks";
+import { rankUserCandidatesBySearch } from "@/features/profile/lib/userCandidateSearch";
 import { usePresenceQuery } from "@/features/presence/hooks";
 import { changeChannelMemberRole } from "@/shared/api/tauri";
 import type {
@@ -40,14 +41,14 @@ import { useProfilePanel } from "@/shared/context/ProfilePanelContext";
 import { useFeedbackToasts } from "@/shared/hooks/useToastEffect";
 import { normalizePubkey } from "@/shared/lib/pubkey";
 import { UserAvatar } from "@/shared/ui/UserAvatar";
+import {
+  MODAL_SEARCH_INPUT_CLASS,
+  MODAL_SEARCH_SHELL_CLASS,
+} from "@/shared/ui/modalSearchStyles";
 import { MembersSidebarAgentControls } from "./MembersSidebarAgentControls";
 import { MembersSidebarMemberCard } from "./MembersSidebarMemberCard";
 import { useMembersSidebarActions } from "./useMembersSidebarActions";
 
-const MEMBERS_SEARCH_SHELL_CLASS =
-  "group/search mt-4 flex cursor-text items-center gap-3 rounded-xl border border-input bg-background px-3 py-2.5 transition-colors duration-150 ease-out hover:border-muted-foreground/40 hover:bg-muted/70 focus-within:border-muted-foreground/50 focus-within:bg-muted/70";
-const MEMBERS_SEARCH_INPUT_CLASS =
-  "block h-6 min-w-0 flex-1 border-0 bg-transparent p-0 text-sm leading-5 text-muted-foreground/55 shadow-none caret-foreground outline-none transition-colors duration-150 ease-out placeholder:text-muted-foreground/55 group-hover/search:text-muted-foreground group-hover/search:placeholder:text-muted-foreground group-focus-within/search:text-foreground group-focus-within/search:placeholder:text-foreground";
 const MEMBER_ADD_RESULT_LIMIT = 50;
 
 function formatAddCandidateName(user: UserSearchResult) {
@@ -58,33 +59,6 @@ function formatAddCandidateName(user: UserSearchResult) {
   );
 }
 
-function scoreAddCandidate(user: UserSearchResult, query: string) {
-  if (query.length === 0) {
-    return null;
-  }
-
-  const labels = [
-    formatAddCandidateName(user),
-    user.nip05Handle?.trim() ?? "",
-    user.isAgent ? "agent" : "",
-  ];
-
-  for (const label of labels) {
-    const lower = label.toLowerCase();
-    if (lower.startsWith(query)) return 0;
-    if (lower.split(/[\s\-_]+/).some((word) => word.startsWith(query))) {
-      return 1;
-    }
-    if (lower.includes(query)) return 2;
-  }
-
-  const pubkey = normalizePubkey(user.pubkey);
-  if (pubkey.startsWith(query)) return 3;
-  if (pubkey.includes(query)) return 4;
-
-  return null;
-}
-
 function memberModalRoleRank(member: ChannelMember) {
   if (member.role === "owner") return 0;
   if (member.role === "admin") return 1;
@@ -300,25 +274,12 @@ export function MembersSidebar({
       });
     }
 
-    return [...candidatesByPubkey.values()]
-      .map((candidate, order) => ({
-        candidate,
-        order,
-        score: scoreAddCandidate(candidate, normalizedDeferredSearchQuery),
-      }))
-      .filter(
-        (item): item is typeof item & { score: number } => item.score !== null,
-      )
-      .sort(
-        (left, right) =>
-          left.score - right.score ||
-          formatAddCandidateName(left.candidate).localeCompare(
-            formatAddCandidateName(right.candidate),
-          ) ||
-          left.order - right.order,
-      )
-      .slice(0, MEMBER_ADD_RESULT_LIMIT)
-      .map(({ candidate }) => candidate);
+    return rankUserCandidatesBySearch({
+      candidates: [...candidatesByPubkey.values()],
+      getLabel: formatAddCandidateName,
+      limit: MEMBER_ADD_RESULT_LIMIT,
+      query: normalizedDeferredSearchQuery,
+    });
   }, [
     canAddMembers,
     isArchivedDiscovery,
@@ -540,14 +501,14 @@ export function MembersSidebar({
               </DialogClose>
             </div>
             <label
-              className={MEMBERS_SEARCH_SHELL_CLASS}
+              className={MODAL_SEARCH_SHELL_CLASS}
               htmlFor="channel-management-search-users"
             >
               <UserRoundPlus className="h-4 w-4 shrink-0 text-muted-foreground/55 transition-colors duration-150 ease-out group-hover/search:text-muted-foreground group-focus-within/search:text-foreground" />
               <input
                 autoCapitalize="none"
                 autoCorrect="off"
-                className={MEMBERS_SEARCH_INPUT_CLASS}
+                className={MODAL_SEARCH_INPUT_CLASS}
                 data-testid="channel-management-search-users"
                 disabled={addMembersMutation.isPending || isArchived}
                 id="channel-management-search-users"
diff --git a/desktop/src/features/profile/lib/userCandidateSearch.test.mjs b/desktop/src/features/profile/lib/userCandidateSearch.test.mjs
new file mode 100644
index 000000000..c7e1a508d
--- /dev/null
+++ b/desktop/src/features/profile/lib/userCandidateSearch.test.mjs
@@ -0,0 +1,98 @@
+import assert from "node:assert/strict";
+import test from "node:test";
+
+import {
+  rankUserCandidatesBySearch,
+  scoreUserCandidate,
+} from "./userCandidateSearch.ts";
+
+function makeUser(overrides = {}) {
+  return {
+    avatarUrl: null,
+    displayName: null,
+    isAgent: false,
+    nip05Handle: null,
+    pubkey: "abcdef1234567890",
+    ...overrides,
+  };
+}
+
+test("scoreUserCandidate ranks display labels before pubkeys", () => {
+  const user = makeUser({
+    displayName: "Alice Johnson",
+    nip05Handle: "alice@example.com",
+  });
+
+  assert.equal(
+    scoreUserCandidate({ label: "Alice Johnson", query: "ali", user }),
+    0,
+  );
+  assert.equal(
+    scoreUserCandidate({ label: "Alice Johnson", query: "joh", user }),
+    1,
+  );
+  assert.equal(
+    scoreUserCandidate({ label: "Alice Johnson", query: "ice", user }),
+    2,
+  );
+  assert.equal(
+    scoreUserCandidate({ label: "Alice Johnson", query: "abcd", user }),
+    3,
+  );
+  assert.equal(
+    scoreUserCandidate({ label: "Alice Johnson", query: "3456", user }),
+    4,
+  );
+});
+
+test("scoreUserCandidate supports agent labels and empty-query defaults", () => {
+  const agent = makeUser({ isAgent: true });
+
+  assert.equal(
+    scoreUserCandidate({ label: "Build Buddy", query: "agent", user: agent }),
+    0,
+  );
+  assert.equal(
+    scoreUserCandidate({ label: "Build Buddy", query: "", user: agent }),
+    null,
+  );
+  assert.equal(
+    scoreUserCandidate({
+      allowEmptyQuery: true,
+      label: "Build Buddy",
+      query: "",
+      user: agent,
+    }),
+    0,
+  );
+});
+
+test("rankUserCandidatesBySearch applies score, label, and stable order sorting", () => {
+  const candidates = [
+    makeUser({ displayName: "Charlie", pubkey: "3000" }),
+    makeUser({ displayName: "Alice", pubkey: "1000" }),
+    makeUser({ displayName: "Beta Team", pubkey: "2000" }),
+    makeUser({ displayName: "Beta Build", pubkey: "2001" }),
+  ];
+
+  assert.deepEqual(
+    rankUserCandidatesBySearch({
+      candidates,
+      getLabel: (user) => user.displayName ?? user.pubkey,
+      limit: 3,
+      query: "be",
+    }).map((user) => user.displayName),
+    ["Beta Build", "Beta Team"],
+  );
+
+  assert.deepEqual(
+    rankUserCandidatesBySearch({
+      allowEmptyQuery: true,
+      candidates,
+      getLabel: (user) => user.displayName ?? user.pubkey,
+      limit: 2,
+      query: "",
+    }).map((user) => user.displayName),
+    ["Alice", "Beta Build"],
+  );
+});
diff --git a/desktop/src/features/profile/lib/userCandidateSearch.ts b/desktop/src/features/profile/lib/userCandidateSearch.ts
new file mode 100644
index 000000000..b3d81b7a4
--- /dev/null
+++ b/desktop/src/features/profile/lib/userCandidateSearch.ts
@@ -0,0 +1,89 @@
+import type { UserSearchResult } from "@/shared/api/types";
+import { normalizePubkey } from "@/shared/lib/pubkey";
+
+type ScoreUserCandidateInput = {
+  allowEmptyQuery?: boolean;
+  label: string;
+  query: string;
+  user: UserSearchResult;
+};
+
+type RankUserCandidatesInput = {
+  allowEmptyQuery?: boolean;
+  candidates: UserSearchResult[];
+  getLabel: (user: UserSearchResult) => string;
+  limit: number;
+  query: string;
+};
+
+export function scoreUserCandidate({
+  allowEmptyQuery = false,
+  label,
+  query,
+  user,
+}: ScoreUserCandidateInput) {
+  const normalizedQuery = query.trim().toLowerCase();
+
+  if (normalizedQuery.length === 0) {
+    return allowEmptyQuery ? 0 : null;
+  }
+
+  const labels = [
+    label,
+    user.nip05Handle?.trim() ?? "",
+    user.isAgent ? "agent" : "",
+  ];
+
+  for (const candidateLabel of labels) {
+    const lower = candidateLabel.toLowerCase();
+    if (lower.startsWith(normalizedQuery)) return 0;
+    if (
+      lower.split(/[\s\-_]+/).some((word) => word.startsWith(normalizedQuery))
+    ) {
+      return 1;
+    }
+    if (lower.includes(normalizedQuery)) return 2;
+  }
+
+  const pubkey = normalizePubkey(user.pubkey);
+  if (pubkey.startsWith(normalizedQuery)) return 3;
+  if (pubkey.includes(normalizedQuery)) return 4;
+
+  return null;
+}
+
+export function rankUserCandidatesBySearch({
+  allowEmptyQuery = false,
+  candidates,
+  getLabel,
+  limit,
+  query,
+}: RankUserCandidatesInput) {
+  return candidates
+    .map((candidate, order) => {
+      const label = getLabel(candidate);
+
+      return {
+        candidate,
+        label,
+        order,
+        score: scoreUserCandidate({
+          allowEmptyQuery,
+          label,
+          query,
+          user: candidate,
+        }),
+      };
+    })
+    .filter(
+      (item): item is typeof item & { score: number } => item.score !== null,
+    )
+    .sort(
+      (left, right) =>
+        left.score - right.score ||
+        left.label.localeCompare(right.label) ||
+        left.order - right.order,
+    )
+    .slice(0, limit)
+    .map(({ candidate }) => candidate);
+}
diff --git a/desktop/src/features/sidebar/ui/NewDirectMessageDialog.tsx b/desktop/src/features/sidebar/ui/NewDirectMessageDialog.tsx
index 2a90dc51d..5b1b37394 100644
--- a/desktop/src/features/sidebar/ui/NewDirectMessageDialog.tsx
+++ b/desktop/src/features/sidebar/ui/NewDirectMessageDialog.tsx
@@ -8,6 +8,7 @@ import {
 import { useIsArchivedPredicate } from "@/features/identity-archive/hooks";
 import { useUserSearchQuery } from "@/features/profile/hooks";
 import { truncatePubkey } from "@/features/profile/lib/identity";
+import { rankUserCandidatesBySearch } from "@/features/profile/lib/userCandidateSearch";
 import { ProfileAvatar } from "@/features/profile/ui/ProfileAvatar";
 import type { UserSearchResult } from "@/shared/api/types";
 import { normalizePubkey } from "@/shared/lib/pubkey";
@@ -19,11 +20,11 @@ import {
   DialogHeader,
   DialogTitle,
 } from "@/shared/ui/dialog";
+import {
+  MODAL_SEARCH_INPUT_CLASS,
+  MODAL_SEARCH_SHELL_CLASS,
+} from "@/shared/ui/modalSearchStyles";
 
-const NEW_DM_SEARCH_SHELL_CLASS =
-  "group/search mt-4 flex cursor-text items-center gap-3 rounded-xl border border-input bg-background px-3 py-2.5 transition-colors duration-150 ease-out hover:border-muted-foreground/40 hover:bg-muted/70 focus-within:border-muted-foreground/50 focus-within:bg-muted/70";
-const NEW_DM_SEARCH_INPUT_CLASS =
-  "block h-6 min-w-0 flex-1 border-0 bg-transparent p-0 text-sm leading-5 text-muted-foreground/55 shadow-none caret-foreground outline-none transition-colors duration-150 ease-out placeholder:text-muted-foreground/55 group-hover/search:text-muted-foreground group-hover/search:placeholder:text-muted-foreground group-focus-within/search:text-foreground group-focus-within/search:placeholder:text-foreground";
 const DIRECT_MESSAGE_RECIPIENT_LIMIT = 50;
 const BUTTON_LABEL_MORPH_DURATION_MS = 220;
 const BUTTON_LABEL_MORPH_EASE = "cubic-bezier(0.23, 1, 0.32, 1)";
@@ -42,33 +43,6 @@ function formatUserName(user: UserSearchResult) {
   );
 }
 
-function scoreRecipientMatch(user: UserSearchResult, query: string) {
-  if (query.length === 0) {
-    return 0;
-  }
-
-  const labels = [
-    formatUserName(user),
-    user.nip05Handle?.trim() ?? "",
-    user.isAgent ? "agent" : "",
-  ];
-
-  for (const label of labels) {
-    const lower = label.toLowerCase();
-    if (lower.startsWith(query)) return 0;
-    if (lower.split(/[\s\-_]+/).some((word) => word.startsWith(query))) {
-      return 1;
-    }
-    if (lower.includes(query)) return 2;
-  }
-
-  const pubkey = normalizePubkey(user.pubkey);
-  if (pubkey.startsWith(query)) return 3;
-  if (pubkey.includes(query)) return 4;
-
-  return null;
-}
-
 function prefersReducedMotion() {
   return (
     typeof window !== "undefined" &&
@@ -276,7 +250,6 @@ export function NewDirectMessageDialog({
   const [selectedRecipientsHeight, setSelectedRecipientsHeight] =
     React.useState(0);
   const deferredSearchQuery = React.useDeferredValue(searchQuery.trim());
-  const normalizedDeferredSearchQuery = deferredSearchQuery.toLowerCase();
   const hasReachedRecipientLimit = selectedUsers.length >= 8;
   const selectedPubkeys = React.useMemo(
     () => new Set(selectedUsers.map((user) => normalizePubkey(user.pubkey))),
@@ -367,30 +340,18 @@ export function NewDirectMessageDialog({
       });
     }
 
-    return [...candidatesByPubkey.values()]
-      .map((candidate, order) => ({
-        candidate,
-        order,
-        score: scoreRecipientMatch(candidate, normalizedDeferredSearchQuery),
-      }))
-      .filter(
-        (item): item is typeof item & { score: number } => item.score !== null,
-      )
-      .sort(
-        (left, right) =>
-          left.score - right.score ||
-          formatUserName(left.candidate).localeCompare(
-            formatUserName(right.candidate),
-          ) ||
-          left.order - right.order,
-      )
-      .slice(0, DIRECT_MESSAGE_RECIPIENT_LIMIT)
-      .map(({ candidate }) => candidate);
+    return rankUserCandidatesBySearch({
+      allowEmptyQuery: true,
+      candidates: [...candidatesByPubkey.values()],
+      getLabel: formatUserName,
+      limit: DIRECT_MESSAGE_RECIPIENT_LIMIT,
+      query: deferredSearchQuery,
+    });
   }, [
     currentPubkey,
+    deferredSearchQuery,
     isArchivedDiscovery,
     managedAgentsQuery.data,
-    normalizedDeferredSearchQuery,
     relayAgentsQuery.data,
     selectedPubkeys,
     userSearchQuery.data,
@@ -456,6 +417,27 @@ export function NewDirectMessageDialog({
     setSubmitErrorMessage(null);
   }
 
+  async function submitDirectMessage() {
+    if (isPending || selectedUsers.length === 0) {
+      return;
+    }
+
+    setSubmitErrorMessage(null);
+
+    try {
+      await onSubmit({
+        pubkeys: selectedUsers.map((user) => user.pubkey),
+      });
+      onOpenChange(false);
+    } catch (error) {
+      setSubmitErrorMessage(
+        error instanceof Error
+          ? error.message
+          : "Failed to open direct message.",
+      );
+    }
+  }
+
   return (
     <Dialog onOpenChange={onOpenChange} open={open}>
       <DialogContent
@@ -476,12 +458,12 @@ export function NewDirectMessageDialog({
               <span className="sr-only">Close</span>
             </DialogClose>
           </div>
-          <label className={NEW_DM_SEARCH_SHELL_CLASS} htmlFor="new-dm-search">
+          <label className={MODAL_SEARCH_SHELL_CLASS} htmlFor="new-dm-search">
             <Search className="h-4 w-4 shrink-0 text-muted-foreground/55 transition-colors duration-150 ease-out group-hover/search:text-muted-foreground group-focus-within/search:text-foreground" />
             <input
               autoCapitalize="none"
               autoCorrect="off"
-              className={NEW_DM_SEARCH_INPUT_CLASS}
+              className={MODAL_SEARCH_INPUT_CLASS}
               data-testid="new-dm-search"
               disabled={isPending}
               id="new-dm-search"
@@ -490,7 +472,19 @@ export function NewDirectMessageDialog({
                 setSubmitErrorMessage(null);
               }}
               onKeyDown={(event) => {
-                if (event.key !== "Enter" || searchResults.length === 0) {
+                if (event.key !== "Enter") {
+                  return;
+                }
+
+                if (searchQuery.trim().length === 0) {
+                  if (selectedUsers.length > 0) {
+                    event.preventDefault();
+                    void submitDirectMessage();
+                  }
+                  return;
+                }
+
+                if (searchResults.length === 0) {
                   return;
                 }
 
@@ -510,26 +504,7 @@ export function NewDirectMessageDialog({
           className="flex flex-col"
           onSubmit={(event) => {
             event.preventDefault();
-
-            if (selectedUsers.length === 0) {
-              return;
-            }
-
-            setSubmitErrorMessage(null);
-
-            void onSubmit({
-              pubkeys: selectedUsers.map((user) => user.pubkey),
-            })
-              .then(() => {
-                onOpenChange(false);
-              })
-              .catch((error) => {
-                setSubmitErrorMessage(
-                  error instanceof Error
-                    ? error.message
-                    : "Failed to open direct message.",
-                );
-              });
+            void submitDirectMessage();
           }}
         >
           <div
diff --git a/desktop/src/shared/ui/modalSearchStyles.ts b/desktop/src/shared/ui/modalSearchStyles.ts
new file mode 100644
index 000000000..6cc572cee
--- /dev/null
+++ b/desktop/src/shared/ui/modalSearchStyles.ts
@@ -0,0 +1,5 @@
+export const MODAL_SEARCH_SHELL_CLASS =
+  "group/search mt-4 flex cursor-text items-center gap-3 rounded-xl border border-input bg-background px-3 py-2.5 transition-colors duration-150 ease-out hover:border-muted-foreground/40 hover:bg-muted/70 focus-within:border-muted-foreground/50 focus-within:bg-muted/70";
+
+export const MODAL_SEARCH_INPUT_CLASS =
+  "block h-6 min-w-0 flex-1 border-0 bg-transparent p-0 text-sm leading-5 text-muted-foreground/55 shadow-none caret-foreground outline-none transition-colors duration-150 ease-out placeholder:text-muted-foreground/55 group-hover/search:text-muted-foreground group-hover/search:placeholder:text-muted-foreground group-focus-within/search:text-foreground group-focus-within/search:placeholder:text-foreground";
diff --git a/desktop/tests/e2e/channels.spec.ts b/desktop/tests/e2e/channels.spec.ts
index e4d541771..6f4f53327 100644
--- a/desktop/tests/e2e/channels.spec.ts
+++ b/desktop/tests/e2e/channels.spec.ts
@@ -355,26 +355,31 @@ test("start a new direct message from the sidebar", async ({ page }) => {
   await expect(page.getByTestId("new-dm-dialog")).toBeVisible();
 
   await page.getByTestId("new-dm-search").fill("charlie");
-  await page
-    .getByTestId(`new-dm-result-${TEST_IDENTITIES.charlie.pubkey}`)
-    .click();
+  await expect(
+    page.getByTestId(`new-dm-result-${TEST_IDENTITIES.charlie.pubkey}`),
+  ).toBeVisible();
+  await page.keyboard.press("Enter");
   await expect(
     page.getByTestId(`new-dm-selected-${TEST_IDENTITIES.charlie.pubkey}`),
   ).toBeVisible();
+  await expect(page.getByTestId("new-dm-search")).toHaveValue("");
   await page
     .getByTestId(`new-dm-selected-${TEST_IDENTITIES.charlie.pubkey}`)
     .click();
   await expect(
     page.getByTestId(`new-dm-selected-${TEST_IDENTITIES.charlie.pubkey}`),
   ).not.toBeVisible();
-  await page
-    .getByTestId(`new-dm-result-${TEST_IDENTITIES.charlie.pubkey}`)
-    .click();
+  await page.getByTestId("new-dm-search").fill("charlie");
+  await expect(
+    page.getByTestId(`new-dm-result-${TEST_IDENTITIES.charlie.pubkey}`),
+  ).toBeVisible();
+  await page.keyboard.press("Enter");
+  await expect(page.getByTestId("new-dm-search")).toHaveValue("");
   await expect(
     page.getByTestId(`new-dm-selected-${TEST_IDENTITIES.charlie.pubkey}`),
   ).toBeVisible();
 
-  await page.getByTestId("new-dm-submit").click();
+  await page.keyboard.press("Enter");
 
   await expect(page.getByTestId("dm-list")).toContainText("charlie");
   await expect(page.getByTestId("chat-title")).toHaveText("charlie");

From 12b2d99b9ea5cc5156f1c22c787e992b82faa8bf Mon Sep 17 00:00:00 2001
From: klopez4212 <klopez4212@gmail.com>
Date: Mon, 15 Jun 2026 22:13:18 +0100
Subject: [PATCH 6/6] Fix stale DM keyboard selection

---
 .../profile/lib/userCandidateSearch.test.mjs  | 31 +++++++++++++++++++
 .../profile/lib/userCandidateSearch.ts        | 23 ++++++++++++++
 .../sidebar/ui/NewDirectMessageDialog.tsx     | 14 +++++++--
 3 files changed, 65 insertions(+), 3 deletions(-)

diff --git a/desktop/src/features/profile/lib/userCandidateSearch.test.mjs b/desktop/src/features/profile/lib/userCandidateSearch.test.mjs
index c7e1a508d..d8b1a2990 100644
--- a/desktop/src/features/profile/lib/userCandidateSearch.test.mjs
+++ b/desktop/src/features/profile/lib/userCandidateSearch.test.mjs
@@ -2,6 +2,7 @@ import assert from "node:assert/strict";
 import test from "node:test";
 
 import {
+  getKeyboardSearchSelection,
   rankUserCandidatesBySearch,
   scoreUserCandidate,
 } from "./userCandidateSearch.ts";
@@ -96,3 +97,33 @@ test("rankUserCandidatesBySearch applies score, label, and stable order sorting"
     ["Alice", "Beta Build"],
   );
 });
+
+test("getKeyboardSearchSelection ignores stale ranked results", () => {
+  const alice = makeUser({ displayName: "Alice", pubkey: "1000" });
+  const charlie = makeUser({ displayName: "Charlie", pubkey: "3000" });
+
+  assert.equal(
+    getKeyboardSearchSelection({
+      currentQuery: "charlie",
+      rankedQuery: "",
+      results: [alice],
+    }),
+    null,
+  );
+  assert.equal(
+    getKeyboardSearchSelection({
+      currentQuery: "charlie",
+      rankedQuery: "charlie",
+      results: [charlie],
+    }),
+    charlie,
+  );
+  assert.equal(
+    getKeyboardSearchSelection({
+      currentQuery: "   ",
+      rankedQuery: "",
+      results: [alice],
+    }),
+    null,
+  );
+});
diff --git a/desktop/src/features/profile/lib/userCandidateSearch.ts b/desktop/src/features/profile/lib/userCandidateSearch.ts
index b3d81b7a4..7447b01c4 100644
--- a/desktop/src/features/profile/lib/userCandidateSearch.ts
+++ b/desktop/src/features/profile/lib/userCandidateSearch.ts
@@ -16,6 +16,12 @@ type RankUserCandidatesInput = {
   query: string;
 };
 
+type KeyboardSearchSelectionInput = {
+  currentQuery: string;
+  rankedQuery: string;
+  results: UserSearchResult[];
+};
+
 export function scoreUserCandidate({
   allowEmptyQuery = false,
   label,
@@ -87,3 +93,20 @@ export function rankUserCandidatesBySearch({
     .slice(0, limit)
     .map(({ candidate }) => candidate);
 }
+
+export function getKeyboardSearchSelection({
+  currentQuery,
+  rankedQuery,
+  results,
+}: KeyboardSearchSelectionInput) {
+  const trimmedCurrentQuery = currentQuery.trim();
+  if (trimmedCurrentQuery.length === 0) {
+    return null;
+  }
+
+  if (rankedQuery.trim() !== trimmedCurrentQuery) {
+    return null;
+  }
+
+  return results[0] ?? null;
+}
diff --git a/desktop/src/features/sidebar/ui/NewDirectMessageDialog.tsx b/desktop/src/features/sidebar/ui/NewDirectMessageDialog.tsx
index 5b1b37394..2a63cd0c5 100644
--- a/desktop/src/features/sidebar/ui/NewDirectMessageDialog.tsx
+++ b/desktop/src/features/sidebar/ui/NewDirectMessageDialog.tsx
@@ -8,7 +8,10 @@ import {
 import { useIsArchivedPredicate } from "@/features/identity-archive/hooks";
 import { useUserSearchQuery } from "@/features/profile/hooks";
 import { truncatePubkey } from "@/features/profile/lib/identity";
-import { rankUserCandidatesBySearch } from "@/features/profile/lib/userCandidateSearch";
+import {
+  getKeyboardSearchSelection,
+  rankUserCandidatesBySearch,
+} from "@/features/profile/lib/userCandidateSearch";
 import { ProfileAvatar } from "@/features/profile/ui/ProfileAvatar";
 import type { UserSearchResult } from "@/shared/api/types";
 import { normalizePubkey } from "@/shared/lib/pubkey";
@@ -484,12 +487,17 @@ export function NewDirectMessageDialog({
                   return;
                 }
 
-                if (searchResults.length === 0) {
+                const keyboardSelection = getKeyboardSearchSelection({
+                  currentQuery: searchQuery,
+                  rankedQuery: deferredSearchQuery,
+                  results: searchResults,
+                });
+                if (!keyboardSelection) {
                   return;
                 }
 
                 event.preventDefault();
-                handleSelectUser(searchResults[0]);
+                handleSelectUser(keyboardSelection);
               }}
               placeholder="Search people and agents"
               ref={searchInputRef}