diff --git a/apps/desktop/src/settings/DesktopClientSettings.test.ts b/apps/desktop/src/settings/DesktopClientSettings.test.ts
index 1c17d58215ea..0ee5bca8864d 100644
--- a/apps/desktop/src/settings/DesktopClientSettings.test.ts
+++ b/apps/desktop/src/settings/DesktopClientSettings.test.ts
@@ -20,6 +20,7 @@ const clientSettings: ClientSettings = {
   confirmQuit: true,
   confirmThreadArchive: true,
   confirmThreadDelete: false,
+  confirmThreadUnpin: false,
   dismissedProviderUpdateNotificationKeys: [],
   diffIgnoreWhitespace: true,
   environmentIdentificationMode: "artwork",
diff --git a/apps/web/src/components/Sidebar.tsx b/apps/web/src/components/Sidebar.tsx
index af7cdc8a94a2..08512864d377 100644
--- a/apps/web/src/components/Sidebar.tsx
+++ b/apps/web/src/components/Sidebar.tsx
@@ -1718,6 +1718,7 @@ export default function Sidebar() {
   const autoSettleOnMerge = useClientSettings((s) => s.sidebarAutoSettleOnMerge);
   const confirmThreadDelete = useClientSettings((s) => s.confirmThreadDelete);
   const confirmThreadArchive = useClientSettings((s) => s.confirmThreadArchive);
+  const confirmThreadUnpin = useClientSettings((s) => s.confirmThreadUnpin);
   const sidebarProjectSortOrder = useClientSettings((s) => s.sidebarProjectSortOrder);
   const timestampFormat = useClientSettings((s) => s.timestampFormat);
   const projectGroupingSettings = useClientSettings(selectProjectGroupingSettings);
@@ -2647,6 +2648,21 @@ export default function Sidebar() {
   const attemptUnpin = useCallback(
     (threadRef: ScopedThreadRef) => {
       void (async () => {
+        if (confirmThreadUnpin) {
+          const api = readLocalApi();
+          const thread = threadByKeyRef.current.get(scopedThreadKey(threadRef));
+          if (api) {
+            const confirmed = await settlePromise(() =>
+              api.dialogs.confirm(
+                [
+                  `Unpin thread "${thread?.title ?? "this thread"}"?`,
+                  "This will move the thread out of your pinned section.",
+                ].join("\n"),
+              ),
+            );
+            if (confirmed._tag === "Failure" || !confirmed.value) return;
+          }
+        }
         const result = await unpinThread(threadRef);
         if (result._tag === "Failure" && !isAtomCommandInterrupted(result)) {
           const error = squashAtomCommandFailure(result);
@@ -2660,7 +2676,7 @@ export default function Sidebar() {
         }
       })();
     },
-    [unpinThread],
+    [confirmThreadUnpin, unpinThread],
   );
 
   const handlePinnedDragEnd = useCallback(
diff --git a/apps/web/src/components/settings/SettingsPanels.tsx b/apps/web/src/components/settings/SettingsPanels.tsx
index 9539f95914cb..154782fc0e3a 100644
--- a/apps/web/src/components/settings/SettingsPanels.tsx
+++ b/apps/web/src/components/settings/SettingsPanels.tsx
@@ -527,6 +527,9 @@ export function useSettingsRestore(onRestored?: () => void) {
       ...(settings.confirmThreadDelete !== DEFAULT_UNIFIED_SETTINGS.confirmThreadDelete
         ? ["Delete confirmation"]
         : []),
+      ...(settings.confirmThreadUnpin !== DEFAULT_UNIFIED_SETTINGS.confirmThreadUnpin
+        ? ["Unpin confirmation"]
+        : []),
       ...(settings.confirmQuit !== DEFAULT_UNIFIED_SETTINGS.confirmQuit
         ? ["Quit confirmation"]
         : []),
@@ -547,6 +550,7 @@ export function useSettingsRestore(onRestored?: () => void) {
       settings.confirmQuit,
       settings.confirmThreadArchive,
       settings.confirmThreadDelete,
+      settings.confirmThreadUnpin,
       settings.addProjectBaseDirectory,
       settings.defaultThreadEnvMode,
       settings.newWorktreesStartFromOrigin,
@@ -658,6 +662,7 @@ export function useSettingsRestore(onRestored?: () => void) {
       addProjectBaseDirectory: DEFAULT_UNIFIED_SETTINGS.addProjectBaseDirectory,
       confirmThreadArchive: DEFAULT_UNIFIED_SETTINGS.confirmThreadArchive,
       confirmThreadDelete: DEFAULT_UNIFIED_SETTINGS.confirmThreadDelete,
+      confirmThreadUnpin: DEFAULT_UNIFIED_SETTINGS.confirmThreadUnpin,
       confirmQuit: DEFAULT_UNIFIED_SETTINGS.confirmQuit,
       textGenerationModelSelection: DEFAULT_UNIFIED_SETTINGS.textGenerationModelSelection,
       fontFamilySans: DEFAULT_UNIFIED_SETTINGS.fontFamilySans,
@@ -2227,6 +2232,32 @@ export function GeneralSettingsPanel() {
           }
         />
 
+        <SettingsRow
+          {...searchableSetting("unpin-confirmation")}
+          description="Ask before unpinning a thread from the pinned section."
+          resetAction={
+            settings.confirmThreadUnpin !== DEFAULT_UNIFIED_SETTINGS.confirmThreadUnpin ? (
+              <SettingResetButton
+                label="unpin confirmation"
+                onClick={() =>
+                  updateSettings({
+                    confirmThreadUnpin: DEFAULT_UNIFIED_SETTINGS.confirmThreadUnpin,
+                  })
+                }
+              />
+            ) : null
+          }
+          control={
+            <Switch
+              checked={settings.confirmThreadUnpin}
+              onCheckedChange={(checked) =>
+                updateSettings({ confirmThreadUnpin: Boolean(checked) })
+              }
+              aria-label="Confirm thread unpinning"
+            />
+          }
+        />
+
         <SettingsRow
           {...searchableSetting("archive-confirmation")}
           description="Require a second click on the inline archive action before a thread is archived."
diff --git a/apps/web/src/components/settings/settingsSearch.ts b/apps/web/src/components/settings/settingsSearch.ts
index e49f77a834eb..7db5a309decf 100644
--- a/apps/web/src/components/settings/settingsSearch.ts
+++ b/apps/web/src/components/settings/settingsSearch.ts
@@ -146,6 +146,11 @@ export const SETTINGS_SEARCH_ITEMS = [
     title: "Add project starts in",
     to: "/settings/general",
   },
+  {
+    id: "unpin-confirmation",
+    title: "Unpin confirmation",
+    to: "/settings/general",
+  },
   {
     id: "archive-confirmation",
     title: "Archive confirmation",
diff --git a/apps/web/src/hooks/useThreadActionMenu.ts b/apps/web/src/hooks/useThreadActionMenu.ts
index 4024fb6b7b7b..16c2e5d69214 100644
--- a/apps/web/src/hooks/useThreadActionMenu.ts
+++ b/apps/web/src/hooks/useThreadActionMenu.ts
@@ -84,6 +84,7 @@ export function useThreadActionMenu(input: {
   const autoSettleOnMerge = useClientSettings((s) => s.sidebarAutoSettleOnMerge);
   const confirmThreadDelete = useClientSettings((s) => s.confirmThreadDelete);
   const confirmThreadArchive = useClientSettings((s) => s.confirmThreadArchive);
+  const confirmThreadUnpin = useClientSettings((s) => s.confirmThreadUnpin);
   const timestampFormat = useClientSettings((s) => s.timestampFormat);
   const { copyToClipboard: copyPathToClipboard } = useCopyToClipboard<{ path: string }>({
     onCopy: ({ path }) => {
@@ -215,9 +216,21 @@ export function useThreadActionMenu(input: {
           case "pin":
             await reportFailure("Failed to pin thread", () => pinThread(threadRef));
             return;
-          case "unpin":
+          case "unpin": {
+            if (confirmThreadUnpin) {
+              const confirmed = await settlePromise(() =>
+                api.dialogs.confirm(
+                  [
+                    `Unpin thread "${thread.title}"?`,
+                    "This will move the thread out of your pinned section.",
+                  ].join("\n"),
+                ),
+              );
+              if (confirmed._tag === "Failure" || !confirmed.value) return;
+            }
             await reportFailure("Failed to unpin thread", () => unpinThread(threadRef));
             return;
+          }
           case "rename":
             onStartRename();
             return;
@@ -315,6 +328,7 @@ export function useThreadActionMenu(input: {
       changeRequest,
       confirmThreadArchive,
       confirmThreadDelete,
+      confirmThreadUnpin,
       copyBranchToClipboard,
       copyPathToClipboard,
       copyThreadIdToClipboard,
diff --git a/packages/contracts/src/settings.ts b/packages/contracts/src/settings.ts
index 0502d303d249..21841492b13c 100644
--- a/packages/contracts/src/settings.ts
+++ b/packages/contracts/src/settings.ts
@@ -156,6 +156,7 @@ export const ClientSettingsSchema = Schema.Struct({
   confirmQuit: Schema.Boolean.pipe(Schema.withDecodingDefault(Effect.succeed(true))),
   confirmThreadArchive: Schema.Boolean.pipe(Schema.withDecodingDefault(Effect.succeed(false))),
   confirmThreadDelete: Schema.Boolean.pipe(Schema.withDecodingDefault(Effect.succeed(true))),
+  confirmThreadUnpin: Schema.Boolean.pipe(Schema.withDecodingDefault(Effect.succeed(false))),
   dismissedProviderUpdateNotificationKeys: Schema.Array(TrimmedNonEmptyString).pipe(
     Schema.withDecodingDefault(Effect.succeed([])),
   ),
@@ -867,6 +868,7 @@ export const ClientSettingsPatch = Schema.Struct({
   confirmQuit: Schema.optionalKey(Schema.Boolean),
   confirmThreadArchive: Schema.optionalKey(Schema.Boolean),
   confirmThreadDelete: Schema.optionalKey(Schema.Boolean),
+  confirmThreadUnpin: Schema.optionalKey(Schema.Boolean),
   diffIgnoreWhitespace: Schema.optionalKey(Schema.Boolean),
   environmentIdentificationMode: Schema.optionalKey(EnvironmentIdentificationMode),
   glassOpacity: Schema.optionalKey(GlassOpacity),