Auto-title ad-hoc workbenches from first message

apps/web/src/auto-workbench-title.test.ts

@@ -0,0 +1,61 @@
+import { describe, expect, test } from "bun:test";
+
+import {
+  AUTO_WORKBENCH_TITLE_MAX,
+  autoNameFromFirstMessage,
+  NEW_WORKBENCH_TITLE,
+  titleFromFirstMessage,
+} from "./auto-workbench-title";
+
+describe("titleFromFirstMessage (CL-6656)", () => {
+  test("trims and collapses whitespace into a single-line title", () => {
+    expect(titleFromFirstMessage("  Help me\nplan  Q3  ")).toBe(
+      "Help me plan Q3",
+    );
+  });
+
+  test("returns undefined for blank or whitespace-only input", () => {
+    expect(titleFromFirstMessage("")).toBeUndefined();
+    expect(titleFromFirstMessage("   \n\t  ")).toBeUndefined();
+  });
+
+  test("keeps a short message intact", () => {
+    expect(titleFromFirstMessage("Draft a launch checklist")).toBe(
+      "Draft a launch checklist",
+    );
+  });
+
+  test("truncates a long message at a word boundary with an ellipsis", () => {
+    const long =
+      "Help me write a detailed competitive analysis of every agent coding tool shipping this quarter";
+    const title = titleFromFirstMessage(long);
+    expect(title).toBeDefined();
+    if (title === undefined) return;
+    expect(title.endsWith("…")).toBe(true);
+    expect(title.length).toBeLessThanOrEqual(AUTO_WORKBENCH_TITLE_MAX + 1);
+    expect(title).not.toContain("shipping");
+  });
+});
+
+describe("autoNameFromFirstMessage (CL-6656)", () => {
+  test("names an ad-hoc New Workbench from the first message", () => {
+    expect(
+      autoNameFromFirstMessage(NEW_WORKBENCH_TITLE, "Plan the Q3 launch"),
+    ).toBe("Plan the Q3 launch");
+  });
+
+  test("leaves prefab and already-renamed titles alone", () => {
+    expect(
+      autoNameFromFirstMessage("Code review", "Review the auth PR"),
+    ).toBeUndefined();
+    expect(
+      autoNameFromFirstMessage("My research bench", "Dig into pricing"),
+    ).toBeUndefined();
+  });
+
+  test("returns undefined when the first message has no usable text", () => {
+    expect(
+      autoNameFromFirstMessage(NEW_WORKBENCH_TITLE, "   "),
+    ).toBeUndefined();
+  });
+});

apps/web/src/auto-workbench-title.ts

@@ -0,0 +1,47 @@
+// CL-6656: ad-hoc ("Just start talking") benches mint as "New Workbench" and
+// used to stay that way in the sidebar. Prefab templates already name the
+// room after the template title; this helper turns the person's first message
+// into a short sidebar title so blank benches get the same treatment once
+// that message is known (at create) — without inventing a second rename API.
+// Callers apply the result through `patchWorkbenchSettings` the same way the
+// sidebar rename does (`chat/name`).
+
+/** Placeholder title for an untitled / blank mint — never a prefab name. */
+export const NEW_WORKBENCH_TITLE = "New Workbench";
+
+/** Sidebar-friendly cap — long enough for a goal phrase, short enough to scan. */
+export const AUTO_WORKBENCH_TITLE_MAX = 48;
+
+/**
+ * Collapse a first user message into a short workbench title.
+ * Returns `undefined` when there is nothing worth naming with (blank /
+ * whitespace-only). Truncates at a word boundary when the cut would land
+ * mid-word past halfway, and appends an ellipsis when truncated.
+ */
+export function titleFromFirstMessage(
+  message: string,
+  maxLength: number = AUTO_WORKBENCH_TITLE_MAX,
+): string | undefined {
+  const collapsed = message.trim().replace(/\s+/g, " ");
+  if (collapsed.length === 0) return undefined;
+  if (collapsed.length <= maxLength) return collapsed;
+
+  const sliced = collapsed.slice(0, maxLength);
+  const lastSpace = sliced.lastIndexOf(" ");
+  const cut =
+    lastSpace > Math.floor(maxLength / 2) ? sliced.slice(0, lastSpace) : sliced;
+  return `${cut.replace(/[.,;:!?]+$/u, "")}…`;
+}
+
+/**
+ * What an ad-hoc auto-name should PATCH as `chat/name`: the derived title when
+ * the room is still the generic "New Workbench" placeholder, otherwise
+ * `undefined` so callers leave prefab (and already-renamed) titles alone.
+ */
+export function autoNameFromFirstMessage(
+  currentTitle: string,
+  firstMessage: string,
+): string | undefined {
+  if (currentTitle !== NEW_WORKBENCH_TITLE) return undefined;
+  return titleFromFirstMessage(firstMessage);
+}

apps/web/src/instant-agent-create.test.ts

@@ -246,4 +246,141 @@ describe("createWorkbenchFromTemplate (CL-6387)", () => {
     // owner reported it from.
     expect(queryClient.getQueryState(staleQueryKey)?.isInvalidated).toBe(true);
   });
+
+  // CL-6656: the prompt-box path mints a blank "New Workbench" and used to
+  // leave that placeholder in the sidebar forever. With a known first
+  // message, create renames via the same `chat/name` settings PATCH the
+  // sidebar rename uses.
+  test("blank create with a first message renames off New Workbench via chat/name", async () => {
+    const navigated: string[] = [];
+    const calls = stubFetch((path) => {
+      if (path.includes("/workflows/definitions")) {
+        return json({ data: [assistantDefinitionWire], nextCursor: null });
+      }
+      if (path.endsWith("/chat/workbenches")) {
+        return json({
+          id: "chan-adhoc",
+          title: NEW_WORKBENCH_TITLE,
+          kind: "workbench",
+          pinned: false,
+          participants: [],
+        });
+      }
+      if (path.endsWith("/chat/workbenches/chan-adhoc/messages")) {
+        return json({
+          id: "msg-1",
+          createdAt: "2026-01-01T00:00:00.000Z",
+          sender: { name: "Sawyer", address: "principal-1" },
+          parts: [{ kind: "text", text: "Plan the Q3 launch" }],
+        });
+      }
+      if (path.endsWith("/chat/workbenches/chan-adhoc/settings")) {
+        return json({
+          id: "chan-adhoc",
+          title: "Plan the Q3 launch",
+          kind: "workbench",
+          pinned: false,
+          participants: [],
+          settings: { "chat/name": "Plan the Q3 launch" },
+          contextWindow: { value: 0, source: "inherit" },
+        });
+      }
+      throw new Error(`unexpected fetch: ${path}`);
+    });
+
+    await createWorkbenchFromTemplate(
+      "tnt_1",
+      "blank",
+      (to) => navigated.push(to),
+      newQueryClient(),
+      undefined,
+      "Plan the Q3 launch",
+    );
+
+    const settingsCall = calls.find((call) =>
+      call.path.endsWith("/chat/workbenches/chan-adhoc/settings"),
+    );
+    expect(settingsCall).toBeDefined();
+    expect(JSON.parse(String(settingsCall?.init?.body))).toEqual({
+      "chat/name": "Plan the Q3 launch",
+    });
+    expect(navigated).toEqual(["/w/chan-adhoc"]);
+  });
+
+  test("prefab create with a first message does not overwrite the template title", async () => {
+    const calls = stubFetch((path) => {
+      if (path.includes("/workflows/definitions")) {
+        return json({ data: [assistantDefinitionWire], nextCursor: null });
+      }
+      if (path.endsWith("/library/templates/code-review")) {
+        return json({
+          id: "code-review",
+          content: serializeWorkbenchTemplateManifest(CODE_REVIEW_TEMPLATE),
+        });
+      }
+      if (path.endsWith("/chat/workbenches")) {
+        return json({
+          id: "chan-1",
+          title: "Code review",
+          kind: "workbench",
+          pinned: false,
+          participants: [],
+        });
+      }
+      if (path.endsWith("/template-blocks/code-review/deploy")) {
+        return json({ id: "def-code-review-block", created: true });
+      }
+      if (path.endsWith("/agent-definitions")) {
+        return json({ ...assistantDefinitionWire, id: "def-reviewer-1" });
+      }
+      if (path.endsWith("/chat/workbenches/chan-1/invite")) {
+        return json({
+          address: "agent:invited",
+          definitionId: "def-reviewer-1",
+        });
+      }
+      if (path.endsWith("/chat/workbenches/chan-1/settings")) {
+        return json({
+          id: "chan-1",
+          title: "Code review",
+          kind: "workbench",
+          pinned: false,
+          participants: [],
+          settings: {},
+          contextWindow: { value: 0, source: "inherit" },
+        });
+      }
+      if (path.endsWith("/chat/workbenches/chan-1/messages")) {
+        return json({
+          id: "msg-1",
+          createdAt: "2026-01-01T00:00:00.000Z",
+          sender: { name: "Sawyer", address: "principal-1" },
+          parts: [{ kind: "text", text: "Review the auth PR" }],
+        });
+      }
+      throw new Error(`unexpected fetch: ${path}`);
+    });
+
+    await createWorkbenchFromTemplate(
+      "tnt_1",
+      "code-review",
+      () => {},
+      newQueryClient(),
+      undefined,
+      "Review the auth PR",
+    );
+
+    const settingsBodies = calls
+      .filter((call) => call.path.endsWith("/chat/workbenches/chan-1/settings"))
+      .map((call) => JSON.parse(String(call.init?.body)));
+    expect(
+      settingsBodies.some(
+        (body) =>
+          typeof body === "object" &&
+          body !== null &&
+          "chat/name" in body &&
+          body["chat/name"] === "Review the auth PR",
+      ),
+    ).toBe(false);
+  });
 });

apps/web/src/instant-agent-create.ts

@@ -35,13 +35,17 @@ import {
 } from "./workbench-templates-api";
 
 import { createAgentDefinition, listAgentDefinitions } from "./agents-api";
+import {
+  autoNameFromFirstMessage,
+  NEW_WORKBENCH_TITLE,
+} from "./auto-workbench-title";
 import { findMyraDefinition } from "./myra-workbench";
 import { workbenchPath } from "./workbench-path";
 
 const log = getLogger("web.instant-agent-create");
 import type { WorkbenchTemplateId } from "./workbench-templates";
 
-export const NEW_WORKBENCH_TITLE = "New Workbench";
+export { NEW_WORKBENCH_TITLE };
 
 /**
  * Marks the two precondition failures below as intentionally
@@ -127,7 +131,10 @@ export type PickGithubRepos = (args: {
  * signed-in person's own opening message once the room and its
  * template participants exist, so it lands after the setup/template
  * greeting rather than racing it — Myra reads the room's actual intent
- * as the next line, not the first.
+ * as the next line, not the first. For a blank / ad-hoc mint (CL-6656)
+ * that same text also renames the room off `NEW_WORKBENCH_TITLE` via
+ * `patchWorkbenchSettings` (`chat/name`), matching the sidebar rename
+ * path; prefab titles are left alone.
  */
 export async function createWorkbenchFromTemplate(
   tenantId: string,
@@ -242,6 +249,19 @@ export async function createWorkbenchFromTemplate(
 
   if (firstMessage !== undefined && firstMessage.trim() !== "") {
     await sendMessage(tenantId, workbench.id, partsForSend(firstMessage, []));
+    // CL-6656: blank / ad-hoc mints stay "New Workbench" until named. When the
+    // prompt box already supplied the opening message, rename via the same
+    // `chat/name` settings PATCH the sidebar rename uses — prefab titles
+    // (`manifest?.title`) are left alone by `autoNameFromFirstMessage`.
+    const autoTitle = autoNameFromFirstMessage(workbench.title, firstMessage);
+    if (autoTitle !== undefined) {
+      await patchWorkbenchSettings(tenantId, workbench.id, {
+        "chat/name": autoTitle,
+      });
+      await queryClient.invalidateQueries({
+        queryKey: workbenchesQueryKeyPrefix(tenantId),
+      });
+    }
   }
 
   navigate(workbenchPath(workbench.id));

apps/web/test/new-workbench-picker.test.tsx

@@ -204,6 +204,20 @@ function stubBlankCreate(
       onSendMessage?.(body);
       return json({ id: "msg_1", createdAt: "2026-01-01T00:00:00.000Z" });
     }
+    if (
+      path.endsWith("/chat/workbenches/chan_new/settings") &&
+      init?.method === "PATCH"
+    ) {
+      return json({
+        id: "chan_new",
+        title: "Get our onboarding docs into shape",
+        kind: "workbench",
+        pinned: false,
+        participants: [],
+        settings: {},
+        contextWindow: { value: 0, source: "inherit" },
+      });
+    }
     return undefined;
   });
 }