feat(web): regenerate selected thread titles

apps/web/src/components/Sidebar.logic.test.ts

@@ -1,6 +1,7 @@
 import { afterEach, beforeEach, describe, expect, it, vi } from "vite-plus/test";
 import {
   archiveSelectedThreadEntries,
+  buildBulkTitleRegenerationContextMenuItem,
   buildMultiSelectThreadContextMenuItems,
   createThreadJumpHintVisibilityController,
   getSidebarThreadIdsToPrewarm,
@@ -82,6 +83,42 @@ describe("isThreadTitleRegenerationPending", () => {
   });
 });
 
+describe("buildBulkTitleRegenerationContextMenuItem", () => {
+  it("counts only threads that can start a new regeneration", () => {
+    expect(
+      buildBulkTitleRegenerationContextMenuItem({
+        supportedCount: 4,
+        actionableCount: 3,
+      }),
+    ).toEqual({
+      id: "regenerate-title",
+      label: "Regenerate titles (3)",
+    });
+  });
+
+  it("shows a disabled progress item when every supported thread is pending", () => {
+    expect(
+      buildBulkTitleRegenerationContextMenuItem({
+        supportedCount: 2,
+        actionableCount: 0,
+      }),
+    ).toEqual({
+      id: "regenerate-title",
+      label: "Regenerating… (2)",
+      disabled: true,
+    });
+  });
+
+  it("omits the action when no selected environment supports it", () => {
+    expect(
+      buildBulkTitleRegenerationContextMenuItem({
+        supportedCount: 0,
+        actionableCount: 0,
+      }),
+    ).toBeNull();
+  });
+});
+
 describe("shouldNavigateAfterProjectRemoval", () => {
   const projectThreads = [{ environmentId: "environment-local", id: "thread-1" }];
 

apps/web/src/components/Sidebar.logic.ts

@@ -42,6 +42,25 @@ export function isThreadTitleRegenerationPending(
 ): boolean {
   return threadTitleRegenerationRemainingMs(thread, nowMs) > 0;
 }
+
+export function buildBulkTitleRegenerationContextMenuItem(input: {
+  supportedCount: number;
+  actionableCount: number;
+}): ContextMenuItem<"regenerate-title"> | null {
+  if (input.supportedCount === 0) return null;
+  if (input.actionableCount === 0) {
+    return {
+      id: "regenerate-title",
+      label: `Regenerating… (${input.supportedCount})`,
+      disabled: true,
+    };
+  }
+  return {
+    id: "regenerate-title",
+    label: `Regenerate titles (${input.actionableCount})`,
+  };
+}
+
 type SidebarProject = {
   id: string;
   title: string;

apps/web/src/components/SidebarV2.tsx

@@ -105,6 +105,7 @@ import { formatRelativeTimeLabel, parseTimestampDate } from "../timestampFormat"
 import type { SidebarThreadSummary } from "../types";
 import { cn } from "~/lib/utils";
 import {
+  buildBulkTitleRegenerationContextMenuItem,
   formatWorkingDurationLabel,
   firstValidTimestampMs,
   hasUnseenCompletion,
@@ -1881,16 +1882,28 @@ export default function SidebarV2() {
       const count = threadKeys.length;
       // Snooze (N) is offered when every selected thread can actually take
       // it — a mixed selection with blocked-on-you work would half-apply.
-      const selectionNow = new Date().toISOString();
-      const snoozableThreads = threadKeys.flatMap((threadKey) => {
+      const selectionNow = new Date();
+      const selectedThreads = threadKeys.flatMap((threadKey) => {
         const thread = threadByKeyRef.current.get(threadKey);
         return thread ? [thread] : [];
       });
-      const canSnoozeSelection = snoozableThreads.every(
+      const canSnoozeSelection = selectedThreads.every(
         (thread) =>
           serverConfigs.get(thread.environmentId)?.environment.capabilities.threadSnooze === true &&
-          canSnooze(thread, { now: selectionNow }),
+          canSnooze(thread, { now: selectionNow.toISOString() }),
       );
+      const titleRegenerationThreads = selectedThreads.filter(
+        (thread) =>
+          serverConfigs.get(thread.environmentId)?.environment.capabilities
+            .threadTitleRegeneration === true,
+      );
+      const regeneratableTitleThreads = titleRegenerationThreads.filter(
+        (thread) => !isThreadTitleRegenerationPending(thread, selectionNow.getTime()),
+      );
+      const titleRegenerationMenuItem = buildBulkTitleRegenerationContextMenuItem({
+        supportedCount: titleRegenerationThreads.length,
+        actionableCount: regeneratableTitleThreads.length,
+      });
       const snoozePresets = resolveSnoozePresets(new Date());
       const clicked = await settlePromise(() =>
         api.contextMenu.show(
@@ -1908,6 +1921,7 @@ export default function SidebarV2() {
                   },
                 ]
               : []),
+            ...(titleRegenerationMenuItem ? [titleRegenerationMenuItem] : []),
             { id: "mark-unread", label: `Mark unread (${count})` },
             { id: "delete", label: `Delete (${count})`, destructive: true },
           ],
@@ -1923,7 +1937,7 @@ export default function SidebarV2() {
           // Post-snooze navigation must skip threads snoozing in this same
           // batch — they are all leaving the card block together.
           const coSnoozingKeys = new Set(threadKeys);
-          for (const thread of snoozableThreads) {
+          for (const thread of selectedThreads) {
             attemptSnooze(scopeThreadRef(thread.environmentId, thread.id), preset, {
               coSnoozingKeys,
             });
@@ -1932,6 +1946,28 @@ export default function SidebarV2() {
         }
         return;
       }
+      if (clicked.value === "regenerate-title") {
+        for (const thread of regeneratableTitleThreads) {
+          const result = await updateThreadMetadata({
+            environmentId: thread.environmentId,
+            input: { threadId: thread.id, regenerateTitle: true },
+          });
+          if (result._tag === "Success") continue;
+          if (!isAtomCommandInterrupted(result)) {
+            const error = squashAtomCommandFailure(result);
+            toastManager.add(
+              stackedThreadToast({
+                type: "error",
+                title: "Failed to regenerate thread titles",
+                description: error instanceof Error ? error.message : "An error occurred.",
+              }),
+            );
+          }
+          return;
+        }
+        clearSelection();
+        return;
+      }
       if (clicked.value === "settle") {
         // Post-settle navigation must skip threads settling in this same
         // batch — they are all leaving the card block together. Rows that
@@ -2003,6 +2039,7 @@ export default function SidebarV2() {
       markThreadUnread,
       removeFromSelection,
       serverConfigs,
+      updateThreadMetadata,
     ],
   );