diff --git a/webview-ui/src/components/chat/ChatTextArea.tsx b/webview-ui/src/components/chat/ChatTextArea.tsx
index 6c541353eb..2352b887e4 100644
--- a/webview-ui/src/components/chat/ChatTextArea.tsx
+++ b/webview-ui/src/components/chat/ChatTextArea.tsx
@@ -955,7 +955,7 @@ const ChatTextArea = forwardRef<HTMLTextAreaElement, ChatTextAreaProps>(
 							placeholder={displayName}
 							options={getApiConfigOptions}
 							onChange={handleApiConfigChange}
-							triggerClassName="w-full text-ellipsis overflow-hidden"
+							triggerClassName="w-full text-ellipsis overflow-hidden min-w-0"
 							itemClassName="group"
 							renderItem={renderApiConfigItem}
 						/>
diff --git a/webview-ui/src/components/modes/ModesView.tsx b/webview-ui/src/components/modes/ModesView.tsx
index 170d03b0e4..d18de20d90 100644
--- a/webview-ui/src/components/modes/ModesView.tsx
+++ b/webview-ui/src/components/modes/ModesView.tsx
@@ -663,29 +663,16 @@ const ModesView = ({ onDone }: ModesViewProps) => {
 															setOpen(false)
 														}}
 														data-testid={`mode-option-${modeConfig.slug}`}>
-														<div className="flex items-center justify-between w-full">
+														<div className="flex items-center justify-between w-full min-w-0">
 															<span
-																style={{
-																	whiteSpace: "nowrap",
-																	overflow: "hidden",
-																	textOverflow: "ellipsis",
-																	flex: 2,
-																	minWidth: 0,
-																}}>
+																className="truncate flex-1 min-w-0 mr-2"
+																title={modeConfig.name}>
 																{modeConfig.name}
 															</span>
 															<span
-																className="text-foreground"
-																style={{
-																	whiteSpace: "nowrap",
-																	overflow: "hidden",
-																	textOverflow: "ellipsis",
-																	direction: "rtl",
-																	textAlign: "right",
-																	flex: 1,
-																	minWidth: 0,
-																	marginLeft: "0.5em",
-																}}>
+																className="text-foreground text-xs opacity-70 truncate flex-shrink-0 max-w-[40%]"
+																style={{ textAlign: "right" }}
+																title={modeConfig.slug}>
 																{modeConfig.slug}
 															</span>
 														</div>
diff --git a/webview-ui/src/components/settings/ApiConfigManager.tsx b/webview-ui/src/components/settings/ApiConfigManager.tsx
index e737678c01..62be19dc24 100644
--- a/webview-ui/src/components/settings/ApiConfigManager.tsx
+++ b/webview-ui/src/components/settings/ApiConfigManager.tsx
@@ -225,7 +225,7 @@ const ApiConfigManager = ({
 				</div>
 			) : (
 				<>
-					<div className="flex items-center gap-1">
+					<div className="flex items-center gap-1 min-w-0">
 						<SearchableSelect
 							value={currentApiConfigName}
 							onValueChange={handleSelectConfig}
@@ -247,42 +247,51 @@ const ApiConfigManager = ({
 							placeholder={t("settings:common.select")}
 							searchPlaceholder={t("settings:providers.searchPlaceholder")}
 							emptyMessage={t("settings:providers.noMatchFound")}
-							className="grow"
+							className="grow min-w-0"
 							data-testid="select-component"
 						/>
-						<StandardTooltip content={t("settings:providers.addProfile")}>
-							<Button variant="ghost" size="icon" onClick={handleAdd} data-testid="add-profile-button">
-								<span className="codicon codicon-add" />
-							</Button>
-						</StandardTooltip>
-						{currentApiConfigName && (
-							<>
-								<StandardTooltip content={t("settings:providers.renameProfile")}>
-									<Button
-										variant="ghost"
-										size="icon"
-										onClick={handleStartRename}
-										data-testid="rename-profile-button">
-										<span className="codicon codicon-edit" />
-									</Button>
-								</StandardTooltip>
-								<StandardTooltip
-									content={
-										isOnlyProfile
-											? t("settings:providers.cannotDeleteOnlyProfile")
-											: t("settings:providers.deleteProfile")
-									}>
-									<Button
-										variant="ghost"
-										size="icon"
-										onClick={handleDelete}
-										data-testid="delete-profile-button"
-										disabled={isOnlyProfile}>
-										<span className="codicon codicon-trash" />
-									</Button>
-								</StandardTooltip>
-							</>
-						)}
+						<div className="flex items-center gap-0.5 flex-shrink-0 ml-1">
+							<StandardTooltip content={t("settings:providers.addProfile")}>
+								<Button
+									variant="ghost"
+									size="icon"
+									onClick={handleAdd}
+									data-testid="add-profile-button"
+									className="flex-shrink-0 min-w-[32px]">
+									<span className="codicon codicon-add" />
+								</Button>
+							</StandardTooltip>
+							{currentApiConfigName && (
+								<>
+									<StandardTooltip content={t("settings:providers.renameProfile")}>
+										<Button
+											variant="ghost"
+											size="icon"
+											onClick={handleStartRename}
+											data-testid="rename-profile-button"
+											className="flex-shrink-0 min-w-[32px]">
+											<span className="codicon codicon-edit" />
+										</Button>
+									</StandardTooltip>
+									<StandardTooltip
+										content={
+											isOnlyProfile
+												? t("settings:providers.cannotDeleteOnlyProfile")
+												: t("settings:providers.deleteProfile")
+										}>
+										<Button
+											variant="ghost"
+											size="icon"
+											onClick={handleDelete}
+											data-testid="delete-profile-button"
+											disabled={isOnlyProfile}
+											className="flex-shrink-0 min-w-[32px]">
+											<span className="codicon codicon-trash" />
+										</Button>
+									</StandardTooltip>
+								</>
+							)}
+						</div>
 					</div>
 					<div className="text-vscode-descriptionForeground text-sm mt-1">
 						{t("settings:providers.description")}
diff --git a/webview-ui/src/components/settings/SettingsView.tsx b/webview-ui/src/components/settings/SettingsView.tsx
index fd3a8a129b..d794c84d44 100644
--- a/webview-ui/src/components/settings/SettingsView.tsx
+++ b/webview-ui/src/components/settings/SettingsView.tsx
@@ -386,8 +386,8 @@ const SettingsView = forwardRef<SettingsViewRef, SettingsViewProps>(({ onDone, t
 
 		const observer = new ResizeObserver((entries) => {
 			for (const entry of entries) {
-				// If container width is less than 500px, switch to compact mode
-				setIsCompactMode(entry.contentRect.width < 500)
+				// If container width is less than 600px, switch to compact mode
+				setIsCompactMode(entry.contentRect.width < 600)
 			}
 		})
 
diff --git a/webview-ui/src/index.css b/webview-ui/src/index.css
index fbb362ca8f..ee340f0ce3 100644
--- a/webview-ui/src/index.css
+++ b/webview-ui/src/index.css
@@ -399,6 +399,47 @@ vscode-dropdown::part(listbox) {
 	min-height: 16px;
 }
 
+/* Ensure checkbox containers don't squeeze */
+.vscrui-checkbox {
+	flex-shrink: 0;
+	min-width: fit-content;
+}
+
+/* Prevent checkbox label text from wrapping inappropriately */
+.vscrui-checkbox label {
+	display: flex;
+	align-items: center;
+	gap: 0.5rem;
+	min-width: 0;
+}
+
+/* Ensure checkbox input maintains size */
+.vscrui-checkbox input[type="checkbox"] {
+	flex-shrink: 0;
+	min-width: 16px;
+	min-height: 16px;
+}
+
+/* VSCode checkbox specific styles to prevent squeezing */
+vscode-checkbox {
+	flex-shrink: 0;
+	min-width: fit-content;
+	display: inline-flex;
+	align-items: center;
+}
+
+/* Ensure VSCode checkbox internals don't squeeze */
+vscode-checkbox::part(control) {
+	flex-shrink: 0;
+	min-width: 16px;
+	min-height: 16px;
+}
+
+vscode-checkbox::part(label) {
+	min-width: 0;
+	margin-left: 0.5rem;
+}
+
 /**
  * @shadcn/ui Overrides / Hacks
  */
@@ -479,3 +520,116 @@ input[cmdk-input]:focus {
 	transition-timing-function: cubic-bezier(0.4, 0, 0.2, 1);
 	transition-duration: 150ms;
 }
+
+/* Responsive utilities for narrow containers */
+@media (max-width: 640px) {
+	.responsive-text {
+		font-size: 0.875rem;
+	}
+
+	.responsive-gap {
+		gap: 0.25rem;
+	}
+
+	.responsive-padding {
+		padding: 0.5rem;
+	}
+}
+
+/* Container query support for components */
+@container (max-width: 600px) {
+	.container-compact {
+		flex-direction: column;
+		gap: 0.5rem;
+	}
+
+	.container-compact .settings-tab {
+		min-width: auto;
+		flex: 1;
+	}
+}
+
+/* Improved flex utilities for narrow containers */
+.flex-responsive {
+	display: flex;
+	flex-wrap: wrap;
+	gap: 0.5rem;
+}
+
+.flex-responsive > * {
+	min-width: 0;
+	flex: 1 1 auto;
+}
+
+/* Better text truncation for dropdowns and selectors */
+.dropdown-text {
+	white-space: nowrap;
+	overflow: hidden;
+	text-overflow: ellipsis;
+	min-width: 0;
+	max-width: 100%;
+}
+
+/* Settings view specific responsive adjustments */
+@container (max-width: 400px) {
+	/* Reduce button sizes in very narrow containers */
+	.settings-view button[class*="size-icon"] {
+		width: 2rem;
+		height: 2rem;
+		padding: 0.25rem;
+	}
+
+	/* Adjust gap between elements */
+	.settings-view .flex.gap-1 {
+		gap: 0.25rem;
+	}
+}
+
+/* Ensure profile selector doesn't overflow */
+.profile-selector-container {
+	min-width: 0;
+	overflow: hidden;
+}
+
+/* Prevent icon buttons from shrinking */
+button[class*="codicon"] {
+	flex-shrink: 0;
+}
+
+/* Additional responsive adjustments for very narrow sidebars */
+@media (max-width: 350px) {
+	/* Ensure button groups stay visible */
+	.flex-shrink-0 {
+		overflow-x: auto;
+		overflow-y: hidden;
+		scrollbar-width: thin;
+	}
+
+	/* Minimum width for button containers */
+	.flex-shrink-0:has(button) {
+		min-width: fit-content;
+	}
+}
+
+/* Ensure all settings checkboxes don't squeeze */
+.settings-view vscode-checkbox,
+[class*="settings"] vscode-checkbox,
+[class*="Settings"] vscode-checkbox {
+	flex-shrink: 0;
+	min-width: fit-content;
+	display: inline-flex;
+	align-items: center;
+}
+
+/* Ensure proper text wrapping and overflow handling */
+.text-wrap {
+	word-wrap: break-word;
+	overflow-wrap: break-word;
+}
+
+.text-ellipsis-safe {
+	white-space: nowrap;
+	overflow: hidden;
+	text-overflow: ellipsis;
+	min-width: 0;
+}