diff --git a/frontend/src/app/pages/AgentChat/tool-ui/ShowUiWidgetView.tsx b/frontend/src/app/pages/AgentChat/tool-ui/ShowUiWidgetView.tsx
index d4b78c07..488e05fa 100644
--- a/frontend/src/app/pages/AgentChat/tool-ui/ShowUiWidgetView.tsx
+++ b/frontend/src/app/pages/AgentChat/tool-ui/ShowUiWidgetView.tsx
@@ -12,7 +12,7 @@ function ShowUiWidgetView({ payload, ambient }: { payload: ShowUiPayload; ambien
   if (payload.component === 'plan') return <PlanWidget props={payload.props} />;
   if (payload.component === 'stats') return <StatsWidget props={payload.props} />;
   if (payload.component === 'links') return <LinksWidget props={payload.props} />;
-  if (payload.component === 'vendored') return <VendoredToolUi name={payload.name} props={payload.props} />;
+  if (payload.component === 'vendored') return <VendoredToolUi name={payload.name} props={payload.props} quietFail={ambient} />;
   return null;
 }
 
diff --git a/frontend/src/app/pages/Dashboard/cards/AgentCard.tsx b/frontend/src/app/pages/Dashboard/cards/AgentCard.tsx
index 7ddbc50c..e9bbf784 100644
--- a/frontend/src/app/pages/Dashboard/cards/AgentCard.tsx
+++ b/frontend/src/app/pages/Dashboard/cards/AgentCard.tsx
@@ -41,7 +41,7 @@ import { openCardContextMenu, isNativeMenuTarget } from '../desktop/openCardCont
 import { agentCardMenuRows } from './agentCardMenuRows';
 import { extractLatestTodos } from '../desktop/agentTodos';
 import { extractLiveSteps } from '../desktop/agentLiveSteps';
-import { extractLatestShowUi, extractPendingAskUi, freezeIfDone } from '@/app/pages/AgentChat/tool-ui/showUiPayload';
+import { extractLatestShowUi, extractPendingAskUi, freezeIfDone, artifactName } from '@/app/pages/AgentChat/tool-ui/showUiPayload';
 import { useDragEndBackstops } from '../hooks/interaction/useDragEndBackstops';
 import { useBrowserPillShot } from '../desktop/useBrowserPillShot';
 import { useAppDispatch, useAppSelector } from '@/shared/hooks';
@@ -700,7 +700,11 @@ const AgentCard: React.FC<Props> = ({
   );
   const pillArtifact = useMemo(() => {
     const artifact = extractLatestShowUi(session.messages || []);
-    return artifact ? freezeIfDone(artifact, session.status === 'running') : null;
+    if (!artifact) return null;
+    // A plan/progress widget posted mid-turn goes stale the moment work continues; while running the
+    // pill prefers living surfaces (browser shot, live steps, todos). Answer widgets still win.
+    if (session.status === 'running' && /plan|progress/i.test(artifactName(artifact))) return null;
+    return freezeIfDone(artifact, session.status === 'running');
   }, [session.messages, session.status]);
   const pillAskPair = useMemo(
     () => (session.status === 'running' ? extractPendingAskUi(session.messages || []) : null),
diff --git a/frontend/src/app/pages/Dashboard/desktop/AgentNarratorPill.tsx b/frontend/src/app/pages/Dashboard/desktop/AgentNarratorPill.tsx
index d8e8200f..e2c361c2 100644
--- a/frontend/src/app/pages/Dashboard/desktop/AgentNarratorPill.tsx
+++ b/frontend/src/app/pages/Dashboard/desktop/AgentNarratorPill.tsx
@@ -40,10 +40,7 @@ function AgentNarratorPill({ label, running, todos, liveSteps, artifact, askPair
   // Live tool steps window to the most recent, since earlier ones are history, not plan.
   const visibleSteps = running && !visibleTodos.length ? (liveSteps || []).slice(-MAX_VISIBLE_TODOS) : [];
   const earlierSteps = running && !visibleTodos.length ? Math.max(0, (liveSteps?.length || 0) - visibleSteps.length) : 0;
-  // A plan/progress widget the agent posted once goes STALE while work continues; live steps outrank
-  // it until the turn ends. Answer-shaped widgets (weather, tables) still win the ladder.
-  const staleplan = running && artifact && /plan|progress/i.test(artifactName(artifact)) && visibleSteps.length > 0;
-  const shownArtifact = staleplan ? null : artifact;
+  const shownArtifact = artifact;
   const ring = selected || highlighted ? { outline: '2px solid #3b82f6', outlineOffset: '2px' } : undefined;
   const liveAsk = askPair && sessionId ? askPair : null;
   // One key per ladder state so a state CHANGE remounts the artifact and replays the one-shot entrance; nothing loops.
@@ -93,7 +90,10 @@ function AgentNarratorPill({ label, running, todos, liveSteps, artifact, askPair
 
       {liveAsk ? (
         <PillArtifactFrame key={artifactKey} name="question">
-          <AskUiBubble pair={liveAsk} sessionId={sessionId!} isPending suppressReveal />
+          {/* One glass surface holds the whole ask (options + Confirm + the type-your-own field); without it the widget's footer floated bare on the canvas. */}
+          <Box sx={{ borderRadius: '16px', background: GLASS, backdropFilter: GLASS_BLUR, WebkitBackdropFilter: GLASS_BLUR, boxShadow: '0 8px 24px rgba(0,0,0,0.32)', px: 1.25, py: 1.25 }}>
+            <AskUiBubble pair={liveAsk} sessionId={sessionId!} isPending suppressReveal />
+          </Box>
         </PillArtifactFrame>
       ) : shownArtifact ? (
         <PillArtifactFrame key={artifactKey} name={artifactName(shownArtifact)}>
diff --git a/frontend/src/toolui/VendoredToolUi.tsx b/frontend/src/toolui/VendoredToolUi.tsx
index b930cb82..eb1da00d 100644
--- a/frontend/src/toolui/VendoredToolUi.tsx
+++ b/frontend/src/toolui/VendoredToolUi.tsx
@@ -2,7 +2,7 @@ import React, { Suspense, useEffect, useState } from 'react';
 import { useThemeMode } from '@/shared/styles/ThemeContext';
 import { TOOL_UI_REGISTRY } from './registry';
 
-interface GuardProps { name: string; children: React.ReactNode }
+interface GuardProps { name: string; quiet?: boolean; children: React.ReactNode }
 
 // A component render throwing must cost exactly one quiet line, never the app: the top-level
 // ErrorBoundary unmounts the whole shell for any uncaught child throw (the linkedin-post {post}
@@ -19,6 +19,7 @@ class ComponentGuard extends React.Component<GuardProps, { failed: boolean }> {
 
   render(): React.ReactNode {
     if (this.state.failed) {
+      if (this.props.quiet) return null;
       return (
         <div style={{ fontSize: '0.75rem', opacity: 0.45, padding: '4px 0', fontStyle: 'italic' }}>
           Couldn't draw the {this.props.name.replace(/-/g, ' ')} view
@@ -34,6 +35,8 @@ interface VendoredToolUiProps {
   props: Record<string, unknown>;
   /** Non-serializable React props (callbacks, live overrides) merged AFTER validation of the wire props. */
   extraProps?: Record<string, unknown>;
+  /** Ambient surfaces (the collapsed pill) show NOTHING on failure; a floating error line on the canvas is worse than absence. */
+  quietFail?: boolean;
 }
 
 type Gate =
@@ -83,7 +86,7 @@ const SkeletonBlock: React.FC<{ name: string }> = ({ name }) => (
 );
 
 /** Validates against the upstream zod contract, then renders the vendored component inside the scoped theme. */
-function VendoredToolUi({ name, props, extraProps }: VendoredToolUiProps): React.ReactElement | null {
+function VendoredToolUi({ name, props, extraProps, quietFail = false }: VendoredToolUiProps): React.ReactElement | null {
   const { mode } = useThemeMode();
   const entry = TOOL_UI_REGISTRY[name];
   const [gate, setGate] = useState<Gate>({ state: 'pending' });
@@ -104,6 +107,7 @@ function VendoredToolUi({ name, props, extraProps }: VendoredToolUiProps): React
   if (gate.state === 'bad') {
     // Schema jargon is for the console; the transcript gets one quiet human line.
     console.warn(`[tool-ui] ${name} payload didn't validate:`, gate.problem);
+    if (quietFail) return null;
     return (
       <div style={{ fontSize: '0.75rem', opacity: 0.45, padding: '4px 0', fontStyle: 'italic' }}>
         Couldn't draw the {name.replace(/-/g, ' ')} view
@@ -111,12 +115,12 @@ function VendoredToolUi({ name, props, extraProps }: VendoredToolUiProps): React
     );
   }
   if (gate.state === 'pending') {
-    return <SkeletonBlock name={name} />;
+    return quietFail ? null : <SkeletonBlock name={name} />;
   }
   const Component = entry.Component;
   return (
     <div className={`tool-ui-scope${mode === 'dark' ? ' dark' : ''}`}>
-      <ComponentGuard name={name}>
+      <ComponentGuard name={name} quiet={quietFail}>
         <Suspense fallback={<SkeletonBlock name={name} />}>
           <Component {...gate.parsed} {...(extraProps || {})} />
         </Suspense>