diff --git a/Gemfile.lock b/Gemfile.lock
index b9c3489b5d..43d4e718bd 100644
--- a/Gemfile.lock
+++ b/Gemfile.lock
@@ -237,7 +237,7 @@ GEM
       logger (~> 1.6)
     letter_opener (1.10.0)
       launchy (>= 2.2, < 4)
-    lexxy (0.1.20.beta)
+    lexxy (0.1.23.beta)
       rails (>= 8.0.2)
     lint_roller (1.1.0)
     logger (1.7.0)
diff --git a/Gemfile.saas.lock b/Gemfile.saas.lock
index 5cd3081555..39af96f957 100644
--- a/Gemfile.saas.lock
+++ b/Gemfile.saas.lock
@@ -313,7 +313,7 @@ GEM
       logger (~> 1.6)
     letter_opener (1.10.0)
       launchy (>= 2.2, < 4)
-    lexxy (0.1.20.beta)
+    lexxy (0.1.23.beta)
       rails (>= 8.0.2)
     lint_roller (1.1.0)
     logger (1.7.0)
diff --git a/app/assets/stylesheets/_global.css b/app/assets/stylesheets/_global.css
index 414d4c6964..13988f0271 100644
--- a/app/assets/stylesheets/_global.css
+++ b/app/assets/stylesheets/_global.css
@@ -219,6 +219,27 @@
   --color-card-7: oklch(var(--lch-purple-medium));
   --color-card-8: oklch(var(--lch-pink-medium));
 
+  /* Colors: Highlighter */
+  --highlight-1: rgb(136, 118, 38);
+  --highlight-2: rgb(185, 94, 6);
+  --highlight-3: rgb(207, 0, 0);
+  --highlight-4: rgb(216, 28, 170);
+  --highlight-5: rgb(144, 19, 254);
+  --highlight-6: rgb(5, 98, 185);
+  --highlight-7: rgb(17, 138, 15);
+  --highlight-8: rgb(148, 82, 22);
+  --highlight-9: rgb(102, 102, 102);
+
+  --highlight-bg-1: rgba(229, 223, 6, 0.3);
+  --highlight-bg-2: rgba(255, 185, 87, 0.3);
+  --highlight-bg-3: rgba(255, 118, 118, 0.3);
+  --highlight-bg-4: rgba(248, 137, 216, 0.3);
+  --highlight-bg-5: rgba(190, 165, 255, 0.3);
+  --highlight-bg-6: rgba(124, 192, 252, 0.3);
+  --highlight-bg-7: rgba(140, 255, 129, 0.3);
+  --highlight-bg-8: rgba(221, 170, 123, 0.3);
+  --highlight-bg-9: rgba(200, 200, 200, 0.3);
+
   /* Colors: Syntax highlighting */
   --color-code-token__att: oklch(var(--lch-blue-dark));
   --color-code-token__comment: oklch(var(--lch-ink-medium));
diff --git a/app/assets/stylesheets/lexxy.css b/app/assets/stylesheets/lexxy.css
index e3f8f8cbdc..7b647caca5 100644
--- a/app/assets/stylesheets/lexxy.css
+++ b/app/assets/stylesheets/lexxy.css
@@ -1,61 +1,39 @@
 @layer components {
+  /* Editor
+  /* ------------------------------------------------------------------------ */
+
   lexxy-editor {
     display: block;
     position: relative;
     overflow: visible;
 
     figure.node--selected {
-      &:not(:has(img)) {
-        outline: var(--focus-ring-size) solid var(--focus-ring-color);
-        outline-offset: var(--focus-ring-offset);
-      }
-
       &:has(img) {
         img {
           outline: var(--focus-ring-size) solid var(--focus-ring-color);
           outline-offset: var(--focus-ring-offset);
         }
       }
-    }
 
-    /* Lexical still uses the `lexxy-editor--empty` class if you have a list
-       started with no other characters. Here, we won't show the placeholder if
-       you've clicked the List button in the toolbar. */
-    &.lexxy-editor--empty {
-      .lexxy-editor__content:not(:has(ul, ol))::before {
-        content: attr(placeholder);
-        color: currentColor;
-        cursor: text;
-        opacity: 0.66;
-        pointer-events: none;
-        position: absolute;
-        white-space: pre-line;
+      &:not(:has(img)) {
+        outline: var(--focus-ring-size) solid var(--focus-ring-color);
+        outline-offset: var(--focus-ring-offset);
       }
     }
   }
 
-  .lexxy-dialog-actions {
-    display: flex;
-    font-size: var(--text-x-small);
-    flex: 1 1 0%;
-    gap: var(--inline-space-half);
-    margin-block-start: var(--block-space-half);
-
-    .btn {
-      --radius: 0.3em;
-
-      inline-size: 100%;
-      justify-content: center;
-
-      &:is([type="submit"]) {
-        --btn-background: var(--card-color, var(--color-link));
-        --btn-color: var(--color-ink-inverted);
-        --focus-ring-color: var(--card-color, var(--color-link));
-      }
-    }
-
-    span {
-      inline-size: 100%;
+  /* Lexical uses the `lexxy-editor--empty` class even if you have a list
+   * started but haven't added other characters. Here, we hide the placeholder
+   * when you click the List button in the toolbar. */
+  .lexxy-editor--empty {
+    .lexxy-editor__content:not(:has(ul, ol))::before {
+      content: attr(placeholder);
+      color: currentColor;
+      cursor: text;
+      opacity: 0.66;
+      pointer-events: none;
+      position: absolute;
+      white-space: pre-line;
     }
   }
 
@@ -64,14 +42,9 @@
     min-block-size: calc(7lh + var(--block-space));
     outline: 0;
 
-    * {
-      &:first-child {
-        margin-block-start: 0;
-      }
-
-      &:last-child {
-        margin-block-end: 0;
-      }
+    /* Allow color highlights to show through a bit */
+    ::selection {
+      background: oklch(var(--lch-blue-light) / 0.5);
     }
   }
 
@@ -81,6 +54,40 @@
     outline: 2px dashed var(--color-selected-dark);
   }
 
+  .lexxy-code-language-picker {
+    -webkit-appearance: none;
+    appearance: none;
+    background-color: var(--color-canvas);
+    background-image: url("data:image/svg+xml,%3Csvg viewBox='0 0 24 24' xmlns='http://www.w3.org/2000/svg'%3E%3Cpath d='m12 19.5c-.7 0-1.3-.3-1.7-.8l-9.8-11.1c-.7-.8-.6-1.9.2-2.6.8-.6 1.9-.6 2.5.2l8.6 9.8c0 .1.2.1.4 0l8.6-9.8c.7-.8 1.8-.9 2.6-.2s.9 1.8.2 2.6l-9.8 11.1c-.4.5-1.1.8-1.7.8z' fill='%23000'/%3E%3C/svg%3E");
+    background-position: center right 0.9em;
+    background-repeat: no-repeat;
+    background-size: 0.5em;
+    border: 1px solid var(--color-ink-light);
+    border-radius: 99rem;
+    color: var(--color-ink);
+    cursor: pointer;
+    font-family: var(--font-base);
+    font-size: var(--text-x-small);
+    font-weight: 500;
+    inset-inline-end: 0;
+    line-height: 1.15lh;
+    margin: 0.75ch 0.75ch 0 0;
+    padding-inline: 1.5ch 1.8em;
+    text-align: start;
+
+    @media (prefers-color-scheme: dark) {
+      background-image: url("data:image/svg+xml,%3Csvg viewBox='0 0 24 24' xmlns='http://www.w3.org/2000/svg'%3E%3Cpath d='m12 19.5c-.7 0-1.3-.3-1.7-.8l-9.8-11.1c-.7-.8-.6-1.9.2-2.6.8-.6 1.9-.6 2.5.2l8.6 9.8c0 .1.2.1.4 0l8.6-9.8c.7-.8 1.8-.9 2.6-.2s.9 1.8.2 2.6l-9.8 11.1c-.4.5-1.1.8-1.7.8z' fill='%23fff'/%3E%3C/svg%3E");
+    }
+
+    option {
+      background-color: var(--color-canvas);
+      color: var(--color-ink);
+    }
+  }
+
+  /* Toolbar
+  /* ------------------------------------------------------------------------ */
+
   lexxy-toolbar {
     --lexxy-toolbar-icon-size: 1em;
 
@@ -96,21 +103,6 @@
     position: sticky;
     inset-block-start: 0;
     z-index: 1;
-
-    dialog {
-      background-color: var(--color-canvas);
-      border: 1px solid var(--color-ink-lighter);
-      border-radius: 0.5em;
-      box-shadow: var(--shadow);
-      color: var(--color-ink);
-      padding: var(--block-space) calc(var(--inline-space) * 1.5);
-      position: absolute;
-      z-index: 1;
-
-      .input[type="url"] {
-        min-inline-size: 30ch;
-      }
-    }
   }
 
   .lexxy-editor__toolbar-button {
@@ -163,42 +155,122 @@
     z-index: 1;
   }
 
-  :where(.lexxy-editor__toolbar-spacer) {
+  .lexxy-editor__toolbar-spacer {
     flex: 1;
   }
 
-  /* Based on .input, .input--select */
-  .lexxy-code-language-picker {
-    -webkit-appearance: none;
-    appearance: none;
+  /* Dropdowns
+  /* ------------------------------------------------------------------------ */
+
+  .lexxy-editor__toolbar-dropdown-content {
+    --lexxy-dropdown-padding: 0.75rem;
+    --lexxy-dropdown-btn-size: 2rem;
+
     background-color: var(--color-canvas);
-    background-image: url("data:image/svg+xml,%3Csvg viewBox='0 0 24 24' xmlns='http://www.w3.org/2000/svg'%3E%3Cpath d='m12 19.5c-.7 0-1.3-.3-1.7-.8l-9.8-11.1c-.7-.8-.6-1.9.2-2.6.8-.6 1.9-.6 2.5.2l8.6 9.8c0 .1.2.1.4 0l8.6-9.8c.7-.8 1.8-.9 2.6-.2s.9 1.8.2 2.6l-9.8 11.1c-.4.5-1.1.8-1.7.8z' fill='%23000'/%3E%3C/svg%3E");
-    background-position: center right 0.9em;
-    background-repeat: no-repeat;
-    background-size: 0.5em;
     border: 1px solid var(--color-ink-lighter);
-    border-radius: 0.3em;
+    border-radius: 0.5em;
+    box-shadow: var(--shadow);
     color: var(--color-ink);
-    font-family: var(--font-base);
+    font-size: var(--text-small);
+    padding: var(--lexxy-dropdown-padding);
+    position: absolute;
+    z-index: 1;
+
+    button {
+      block-size: var(--lexxy-dropdown-btn-size);
+    }
+  }
+
+  .lexxy-editor__toolbar-dropdown-actions {
+    display: flex;
     font-size: var(--text-x-small);
+    flex: 1 1 0%;
+    gap: var(--lexxy-dropdown-padding);
+    margin-block-start: var(--lexxy-dropdown-padding);
+
+    .btn {
+      --radius: 99rem;
+
+      inline-size: 100%;
+    }
+
+    .btn[type="submit"] {
+      --btn-background: var(--card-color, var(--color-link));
+      --btn-color: var(--color-ink-inverted);
+      --focus-ring-color: var(--card-color, var(--color-link));
+    }
+
+    span {
+      inline-size: 100%;
+    }
+  }
+
+  lexxy-link-dropdown {
+    .input {
+      min-inline-size: 30ch;
+    }
+  }
+
+  lexxy-highlight-dropdown {
+    --gap: 0.5ch;
+
+    [data-button-group] {
+      display: flex;
+      flex-direction: row;
+      flex-wrap: wrap;
+      gap: var(--gap);
+
+      + & {
+        margin-block-start: var(--gap);
+      }
+    }
+  }
+
+  .lexxy-highlight-button {
+    --outline-color: oklch(var(--lch-ink-darkest) / 0.2);
+
+    appearance: none;
+    background: var(--color-canvas);
+    border: none;
+    border-radius: 0.5ch;
+    display: grid;
     font-weight: 500;
-    inset-inline-end: 0;
-    line-height: inherit;
-    margin: 0.3em 0.3em 0 0;
-    padding: 0.5em 1.8em 0.5em 1.2em;
-    text-align: start;
+    inline-size: var(--lexxy-dropdown-btn-size);
+    place-items: center;
+    position: relative;
+    outline: none;
 
-    @media (prefers-color-scheme: dark) {
-      background-image: url("data:image/svg+xml,%3Csvg viewBox='0 0 24 24' xmlns='http://www.w3.org/2000/svg'%3E%3Cpath d='m12 19.5c-.7 0-1.3-.3-1.7-.8l-9.8-11.1c-.7-.8-.6-1.9.2-2.6.8-.6 1.9-.6 2.5.2l8.6 9.8c0 .1.2.1.4 0l8.6-9.8c.7-.8 1.8-.9 2.6-.2s.9 1.8.2 2.6l-9.8 11.1c-.4.5-1.1.8-1.7.8z' fill='%23fff'/%3E%3C/svg%3E");
+    &:after {
+      content: "Aa";
     }
 
-    option {
-      background-color: var(--color-canvas);
-      color: var(--color-ink);
+    &:hover,
+    &[aria-pressed="true"] {
+      box-shadow: 0 0 0 1px var(--color-canvas), 0 0 0 3px var(--outline-color);
+    }
+
+    &[aria-pressed="true"] {
+      --outline-color: var(--color-link);
+
+      &:after {
+        content: "✓";
+      }
+    }
+  }
+
+  .lexxy-editor__toolbar-dropdown-reset {
+    background: var(--color-canvas);
+    border: 1px solid var(--color-ink-light);
+    border-radius: 99rem;
+    inline-size: 100%;
+    margin-block-start: var(--lexxy-dropdown-padding);
+
+    &[disabled] {
+      display: none;
     }
   }
 
-  /* Prompt
+  /* Prompt ,enu (@mentions, etc.)
   /* ------------------------------------------------------------------------ */
 
   .lexxy-prompt-menu {
diff --git a/app/assets/stylesheets/rich-text-content.css b/app/assets/stylesheets/rich-text-content.css
index 2d465c935b..fdb8224fc1 100644
--- a/app/assets/stylesheets/rich-text-content.css
+++ b/app/assets/stylesheets/rich-text-content.css
@@ -28,6 +28,14 @@
       }
     }
 
+    :where(ol, ul) {
+      padding-inline-start: 3ch;
+    }
+
+    :where(li:has(li)) {
+      list-style: none;
+    }
+
     :where(b, strong, .lexxy-content__bold) {
       font-weight: 700;
     }
@@ -40,6 +48,10 @@
       text-decoration: line-through;
     }
 
+    :where(mark, .lexxy-content__highlight) {
+      background-color: transparent;
+      color: inherit;
+    }
 
     :where(p, blockquote) {
       letter-spacing: -0.005ch;
@@ -201,14 +213,17 @@
     color: color-mix(in oklch, var(--color-ink) 66%, transparent);
     font-size: var(--text-small);
 
-    .input {
+    textarea {
       --input-border-radius: 0.3em;
       --input-border-size: 0;
       --input-padding: 0;
 
+      background-color: var(--input-background, transparent);
+      border: none;
       color: inherit;
       inline-size: 100%;
       max-inline-size: 100%;
+      resize: none;
       text-align: center;
 
       &:focus {
@@ -274,7 +289,8 @@
     display: flex;
     flex-wrap: wrap;
     gap: 1ch;
-    inline-size: auto;
+    inline-size: 100%;
+    margin-inline: 0;
 
     .attachment__caption {
       display: grid;
diff --git a/test/system/smoke_test.rb b/test/system/smoke_test.rb
index e4bc9cae98..539921b939 100644
--- a/test/system/smoke_test.rb
+++ b/test/system/smoke_test.rb
@@ -24,7 +24,7 @@ class SmokeTest < ApplicationSystemTestCase
 
     within("form lexxy-editor figure.attachment[data-content-type='image/jpeg']") do
       assert_selector "img[src*='/rails/active_storage']"
-      assert_selector "figcaption input[placeholder='moon.jpg']"
+      assert_selector "figcaption textarea[placeholder='moon.jpg']"
     end
 
     click_on "Post"