diff --git a/apps/web/src/auto-workbench-title.ts b/apps/web/src/auto-workbench-title.ts
index 93346b49f..27ad38b77 100644
--- a/apps/web/src/auto-workbench-title.ts
+++ b/apps/web/src/auto-workbench-title.ts
@@ -6,22 +6,31 @@
 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;
+export const AUTO_WORKBENCH_TITLE_MAX = 40;
 
-// Truncates at a word boundary when the cut would land mid-word past
-// halfway, appending an ellipsis.
+const LEADING_FILLER =
+  /^(?:(?:hey|hi|hello|so|ok|okay)[,\s]+)?(?:(?:can|could|would|will)\s+you\s+|please\s+|pls\s+|i(?:'d| would)? (?:like|want|need) (?:you )?to\s+)+(?:please\s+)?/iu;
+
+// First sentence or clause, filler stripped, first letter capitalised, cut at
+// a word boundary with an ellipsis when it still exceeds the cap.
 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 clause = (collapsed.split(/[.!?:;]+(?:\s|$)|\s[-—–]\s/u)[0] ?? "").replace(
+    LEADING_FILLER,
+    "",
+  );
+  const cleaned = clause.replace(/[\s.,;:!?]+$/u, "");
+  if (cleaned.length === 0) return undefined;
+  const title = cleaned.charAt(0).toLocaleUpperCase() + cleaned.slice(1);
+  if (title.length <= maxLength) return title;
 
-  const sliced = collapsed.slice(0, maxLength);
+  const sliced = title.slice(0, maxLength);
   const lastSpace = sliced.lastIndexOf(" ");
   const cut = lastSpace > Math.floor(maxLength / 2) ? sliced.slice(0, lastSpace) : sliced;
-  return `${cut.replace(/[.,;:!?]+$/u, "")}…`;
+  return `${cut.replace(/[\s.,;:!?]+$/u, "")}…`;
 }
 
 // `undefined` unless the workbench is still the generic placeholder, so
diff --git a/apps/web/src/pages/new-workbench-picker.tsx b/apps/web/src/pages/new-workbench-picker.tsx
index 73f4150ab..511e04bd9 100644
--- a/apps/web/src/pages/new-workbench-picker.tsx
+++ b/apps/web/src/pages/new-workbench-picker.tsx
@@ -9,6 +9,7 @@ import { reportError } from "@corbits/error-sink";
 
 import { useBench } from "../bench-context";
 import { workbenchKeys } from "../chat-path";
+import { NEW_WORKBENCH_TITLE, titleFromFirstMessage } from "@/auto-workbench-title";
 import { createWorkbench, WorkbenchCreateError } from "../workbench-create";
 import { useNavigate } from "../navigation";
 import { ProviderSkipBanner } from "../provider-skip-banner";
@@ -29,12 +30,6 @@ export function describeWorkbenchCreateFailure(cause: unknown, refId?: string):
   return refId === undefined ? message : `${message} Reference: ${refId}`;
 }
 
-/** A workbench's name is its opening ask, trimmed. */
-function workbenchName(prompt: string): string {
-  const trimmed = prompt.trim();
-  return trimmed === "" ? "Workbench" : trimmed.slice(0, 60);
-}
-
 export function NewWorkbenchPickerRoute() {
   const navigate = useNavigate();
   const queryClient = useQueryClient();
@@ -51,7 +46,7 @@ export function NewWorkbenchPickerRoute() {
     }) =>
       createWorkbench({
         benchTenantId,
-        name: workbenchName(openingMessage),
+        name: titleFromFirstMessage(openingMessage) ?? NEW_WORKBENCH_TITLE,
         openingMessage,
       }),
     onSuccess: (tenantId, variables) => {