diff --git a/apps/web/src/components/LegacySidebar.tsx b/apps/web/src/components/LegacySidebar.tsx
index ea910905efe0..a24955f54a64 100644
--- a/apps/web/src/components/LegacySidebar.tsx
+++ b/apps/web/src/components/LegacySidebar.tsx
@@ -702,6 +702,7 @@ export const SidebarThreadRow = memo(function SidebarThreadRow(props: SidebarThr
       ref={rowRef}
       className="w-full"
       data-thread-item
+      data-pending-question={thread.hasPendingUserInput || undefined}
       onMouseLeave={handleMouseLeave}
       onBlurCapture={handleBlurCapture}
     >
@@ -713,7 +714,7 @@ export const SidebarThreadRow = memo(function SidebarThreadRow(props: SidebarThr
         className={`${resolveThreadRowClassName({
           isActive,
           isSelected,
-        })} relative isolate`}
+        })} relative isolate${thread.hasPendingUserInput ? " sidebar-question-pending" : ""}`}
         onClick={handleRowClick}
         onDoubleClick={handleRowDoubleClick}
         onKeyDown={handleRowKeyDown}
@@ -2858,6 +2859,7 @@ interface SidebarProjectsContentProps {
   suppressProjectClickForContextMenuRef: React.RefObject<boolean>;
   attachProjectListAutoAnimateRef: (node: HTMLElement | null) => void;
   projectsLength: number;
+  navigateToThread: (threadRef: ScopedThreadRef) => void;
 }
 
 const SidebarProjectsContent = memo(function SidebarProjectsContent(
@@ -2923,6 +2925,7 @@ const SidebarProjectsContent = memo(function SidebarProjectsContent(
 
   return (
     <SidebarContent
+      onPendingQuestionNavigate={props.navigateToThread}
       className="gap-0"
       fixedHeader={
         // Lifted above the stage backdrop, whose fade bleeds below the
@@ -3762,6 +3765,7 @@ export default function LegacySidebar() {
         suppressProjectClickForContextMenuRef={suppressProjectClickForContextMenuRef}
         attachProjectListAutoAnimateRef={attachProjectListAutoAnimateRef}
         projectsLength={projects.length}
+        navigateToThread={navigateToThread}
       />
       <SidebarChromeFooter />
     </>
diff --git a/apps/web/src/components/Sidebar.tsx b/apps/web/src/components/Sidebar.tsx
index 4509fde6ceb9..c74d6a908e1b 100644
--- a/apps/web/src/components/Sidebar.tsx
+++ b/apps/web/src/components/Sidebar.tsx
@@ -1176,6 +1176,7 @@ const SidebarThreadRow = memo(function SidebarThreadRow(props: {
   // content; surface is reserved for interaction (hover, multi-select, route).
   const rowSurfaceClassName = cn(
     "group/sidebar-row relative w-full cursor-pointer overflow-hidden rounded-md text-left outline-none select-none",
+    thread.hasPendingUserInput && "sidebar-question-pending",
     props.isActive
       ? "bg-sidebar-row-active text-sidebar-foreground"
       : isSelected
@@ -1321,6 +1322,7 @@ const SidebarThreadRow = memo(function SidebarThreadRow(props: {
     return (
       <li
         data-thread-item
+        data-pending-question={thread.hasPendingUserInput || undefined}
         className="list-none [content-visibility:auto] [contain-intrinsic-size:auto_34px]"
       >
         <Tooltip>
@@ -1472,6 +1474,7 @@ const SidebarThreadRow = memo(function SidebarThreadRow(props: {
   return (
     <li
       data-thread-item
+      data-pending-question={thread.hasPendingUserInput || undefined}
       ref={sortable?.setNodeRef}
       style={
         sortable
@@ -3604,6 +3607,7 @@ export default function Sidebar() {
     <>
       <SidebarChromeHeader isElectron={isElectron} />
       <SidebarContent
+        onPendingQuestionNavigate={navigateToThread}
         className="gap-0"
         fixedHeader={
           // Lifted above the stage backdrop, whose fade bleeds below the
diff --git a/apps/web/src/components/chat/ComposerPendingUserInputPanel.tsx b/apps/web/src/components/chat/ComposerPendingUserInputPanel.tsx
index 2a7df2488233..87f1d0f54eef 100644
--- a/apps/web/src/components/chat/ComposerPendingUserInputPanel.tsx
+++ b/apps/web/src/components/chat/ComposerPendingUserInputPanel.tsx
@@ -9,6 +9,7 @@ import { CheckIcon } from "lucide-react";
 import { Collapsible, CollapsiblePanel, CollapsibleTrigger } from "../ui/collapsible";
 import { cn } from "~/lib/utils";
 import { ComposerBanner } from "./ComposerBanner";
+import ChatMarkdown from "../ChatMarkdown";
 
 interface PendingUserInputPanelProps {
   pendingUserInputs: PendingUserInput[];
@@ -202,7 +203,11 @@ const ComposerPendingUserInputCard = memo(function ComposerPendingUserInputCard(
       </CollapsibleTrigger>
       <CollapsiblePanel>
         <ComposerBanner.Body className="pe-1 pb-1">
-          <p className="text-sm text-foreground/85">{activeQuestion.question}</p>
+          <ChatMarkdown
+            text={activeQuestion.question}
+            cwd={undefined}
+            className="text-sm text-foreground/85"
+          />
           {activeQuestion.multiSelect ? (
             <p className="mt-1 text-secondary-label text-xs">Select one or more options.</p>
           ) : null}
diff --git a/apps/web/src/components/chat/MessagesTimeline.logic.ts b/apps/web/src/components/chat/MessagesTimeline.logic.ts
index 36c90c89563c..0da14a8e7048 100644
--- a/apps/web/src/components/chat/MessagesTimeline.logic.ts
+++ b/apps/web/src/components/chat/MessagesTimeline.logic.ts
@@ -48,6 +48,7 @@ function singleToolCallLabel(entry: WorkLogEntry): string {
 }
 
 export function workEntryDisplayLabel(entry: WorkLogEntry, workspaceRoot: string | undefined) {
+  if (entry.userInputSummary) return entry.label;
   const toolPresentation = resolveWorkEntryToolPresentation(entry);
   if (toolPresentation) return toolPresentation.displayName;
   if (entry.command) return entry.command;
diff --git a/apps/web/src/components/chat/MessagesTimeline.tsx b/apps/web/src/components/chat/MessagesTimeline.tsx
index 4e55991f8703..f46f767fddd6 100644
--- a/apps/web/src/components/chat/MessagesTimeline.tsx
+++ b/apps/web/src/components/chat/MessagesTimeline.tsx
@@ -3147,7 +3147,9 @@ const PlainWorkEntryRow = memo(function PlainWorkEntryRow(props: {
         : "text-foreground/80";
   const accessibleDisplayText = showFailedIndicator
     ? `${previewText}, tool call failed`
-    : previewText;
+    : workEntry.userInputSummary
+      ? `${previewText}: ${workEntry.userInputSummary}`
+      : previewText;
   const rowToggleProps = canExpand
     ? {
         role: "button" as const,
@@ -3192,7 +3194,8 @@ const PlainWorkEntryRow = memo(function PlainWorkEntryRow(props: {
             <p className="flex min-w-0 w-full items-baseline gap-1.5 text-sm leading-relaxed">
               <span
                 className={cn(
-                  "min-w-0 flex-1",
+                  "min-w-0",
+                  workEntry.userInputSummary ? "shrink-0" : "flex-1",
                   expanded || (commandMatchesVisibleLabel && !canExpand)
                     ? "whitespace-pre-wrap break-words select-text"
                     : "truncate",
@@ -3203,6 +3206,11 @@ const PlainWorkEntryRow = memo(function PlainWorkEntryRow(props: {
               >
                 {previewText}
               </span>
+              {workEntry.userInputSummary ? (
+                <span className="min-w-0 truncate text-secondary-label">
+                  {workEntry.userInputSummary}
+                </span>
+              ) : null}
             </p>
           </div>
           {showFailedIndicator &&
diff --git a/apps/web/src/components/sidebar/SidebarQuestionIndicators.tsx b/apps/web/src/components/sidebar/SidebarQuestionIndicators.tsx
new file mode 100644
index 000000000000..11b051653cca
--- /dev/null
+++ b/apps/web/src/components/sidebar/SidebarQuestionIndicators.tsx
@@ -0,0 +1,50 @@
+import { scopeThreadRef, scopedThreadKey } from "@t3tools/client-runtime/environment";
+import type { ScopedThreadRef } from "@t3tools/contracts";
+import { ArrowDownIcon } from "lucide-react";
+import { useMemo, useRef } from "react";
+import { Button } from "~/components/ui/button";
+import { useThreadShells } from "~/state/entities";
+
+/** Keeps all pending questions reachable, including threads in collapsed lists. */
+export function SidebarQuestionIndicators({
+  onNavigate,
+}: {
+  onNavigate: (threadRef: ScopedThreadRef) => void;
+}) {
+  const threads = useThreadShells();
+  const pending = useMemo(
+    () =>
+      threads
+        .filter((thread) => thread.archivedAt === null && thread.hasPendingUserInput)
+        .toSorted((a, b) => b.updatedAt.localeCompare(a.updatedAt))
+        .map((thread) => scopeThreadRef(thread.environmentId, thread.id)),
+    [threads],
+  );
+  const lastTarget = useRef<string | null>(null);
+  const count = pending.length;
+
+  return (
+    <div className="shrink-0 px-2 pb-2">
+      <Button
+        variant="outline"
+        size="sm"
+        disabled={count === 0}
+        aria-label={`Next pending question (${count})`}
+        className="w-full justify-between border-indigo-400/50 bg-sidebar text-indigo-600 transition-none active:scale-100 dark:bg-sidebar dark:text-indigo-300 [--control-icon-color:currentColor]"
+        onClick={() => {
+          const nextIndex =
+            (pending.findIndex((ref) => scopedThreadKey(ref) === lastTarget.current) + 1) % count;
+          const next = pending[nextIndex];
+          if (!next) return;
+          lastTarget.current = scopedThreadKey(next);
+          onNavigate(next);
+        }}
+      >
+        <span>
+          Needs input · <span className="tabular-nums">{count}</span>
+        </span>
+        <ArrowDownIcon aria-hidden="true" className="size-4" />
+      </Button>
+    </div>
+  );
+}
diff --git a/apps/web/src/components/ui/sidebar.tsx b/apps/web/src/components/ui/sidebar.tsx
index 624798e19f54..9341ce94f891 100644
--- a/apps/web/src/components/ui/sidebar.tsx
+++ b/apps/web/src/components/ui/sidebar.tsx
@@ -7,6 +7,7 @@ import { cn } from "~/lib/utils";
 import { Button } from "~/components/ui/button";
 import { Input } from "~/components/ui/input";
 import { ScrollArea } from "~/components/ui/scroll-area";
+import { SidebarQuestionIndicators } from "~/components/sidebar/SidebarQuestionIndicators";
 import { Separator } from "~/components/ui/separator";
 import {
   Sheet,
@@ -692,24 +693,31 @@ function SidebarSeparator({ className, ...props }: React.ComponentProps<typeof S
 function SidebarContent({
   className,
   fixedHeader,
+  onPendingQuestionNavigate,
   ...props
 }: React.ComponentProps<"div"> & {
   fixedHeader?: React.ReactNode;
+  onPendingQuestionNavigate?: React.ComponentProps<typeof SidebarQuestionIndicators>["onNavigate"];
 }) {
   return (
     <>
       {fixedHeader ? <div className="w-full shrink-0">{fixedHeader}</div> : null}
-      <ScrollArea hideScrollbars scrollFade className="h-auto min-h-0 flex-1">
-        <div
-          className={cn(
-            "flex w-full min-w-0 flex-col gap-2 group-data-[collapsible=icon]:overflow-hidden",
-            className,
-          )}
-          data-sidebar="content"
-          data-slot="sidebar-content"
-          {...props}
-        />
-      </ScrollArea>
+      <div className="relative flex min-h-0 flex-1 flex-col">
+        {onPendingQuestionNavigate ? (
+          <SidebarQuestionIndicators onNavigate={onPendingQuestionNavigate} />
+        ) : null}
+        <ScrollArea hideScrollbars scrollFade className="h-auto min-h-0 flex-1">
+          <div
+            className={cn(
+              "flex w-full min-w-0 flex-col gap-2 group-data-[collapsible=icon]:overflow-hidden",
+              className,
+            )}
+            data-sidebar="content"
+            data-slot="sidebar-content"
+            {...props}
+          />
+        </ScrollArea>
+      </div>
     </>
   );
 }
diff --git a/apps/web/src/index.css b/apps/web/src/index.css
index 54bb5b70d5fa..226eaa9bda2f 100644
--- a/apps/web/src/index.css
+++ b/apps/web/src/index.css
@@ -1909,3 +1909,14 @@ code {
     transform: scaleX(0.9);
   }
 }
+
+/* Static emphasis keeps pending questions visible without ongoing animation. */
+.sidebar-question-pending::after {
+  content: "";
+  position: absolute;
+  inset: 0;
+  z-index: 20;
+  pointer-events: none;
+  border: 1px solid var(--color-indigo-400);
+  border-radius: inherit;
+}
diff --git a/apps/web/src/session-logic.ts b/apps/web/src/session-logic.ts
index 47fe1b49ac32..31c350c2ce79 100644
--- a/apps/web/src/session-logic.ts
+++ b/apps/web/src/session-logic.ts
@@ -88,6 +88,7 @@ export interface WorkLogEntry {
   toolCallId?: string;
   label: string;
   detail?: string;
+  userInputSummary?: string;
   viewedImagePath?: string;
   command?: string;
   rawCommand?: string;
@@ -845,6 +846,7 @@ export function deriveWorkLogEntries(
 ): WorkLogEntry[] {
   const ordered = [...activities].toSorted(compareActivitiesByOrder);
   const entries: DerivedWorkLogEntry[] = [];
+  const questionsByRequestId = new Map<string, ReadonlyArray<UserInputQuestion>>();
   for (const activity of ordered) {
     if (activity.tone !== "error" && isWorktreeSetupActivity(activity.kind)) continue;
     if (activity.kind === "tool.started") continue;
@@ -861,7 +863,62 @@ export function deriveWorkLogEntries(
     if (isNoContentRuntimeWarning(activity)) continue;
     if (isPlanBoundaryToolActivity(activity)) continue;
     if (isAgentInternalActivity(activity)) continue;
-    entries.push(toDerivedWorkLogEntry(activity));
+    const entry = toDerivedWorkLogEntry(activity);
+    if (activity.kind === "user-input.requested" || activity.kind === "user-input.resolved") {
+      const payload = asRecord(activity.payload);
+      const requestId = asTrimmedString(payload?.requestId);
+      if (activity.kind === "user-input.requested" && requestId) {
+        const questions = parseUserInputQuestions(payload);
+        if (questions) questionsByRequestId.set(requestId, questions);
+      } else if (activity.kind === "user-input.resolved") {
+        const answers = asRecord(payload?.answers);
+        if (answers) {
+          const questions = requestId ? questionsByRequestId.get(requestId) : undefined;
+          const submittedAnswers = Object.entries(answers).flatMap(([id, value]) => {
+            const question = questions?.find((question) => question.id === id);
+            const values =
+              typeof value === "string"
+                ? [value]
+                : Array.isArray(value)
+                  ? value
+                  : asRecord(value)?.answers;
+            const answer = Array.isArray(values)
+              ? values
+                  .filter((part): part is string => typeof part === "string")
+                  .map(
+                    (part) =>
+                      question?.options.find((option) => (option.value ?? option.label) === part)
+                        ?.label ?? part,
+                  )
+                  .join(", ")
+              : "";
+            return answer.trim() ? [{ id, answer }] : [];
+          });
+          const detail = submittedAnswers
+            .map(({ id, answer }) => {
+              const question = questions?.find((question) => question.id === id);
+              if (!question) return `${id}\nAnswer: ${answer}`;
+              const options = question.options.map(
+                (option) =>
+                  `- ${option.label}${option.description ? `: ${option.description}` : ""}`,
+              );
+              return [question.header, question.question, ...options, `Answer: ${answer}`].join(
+                "\n",
+              );
+            })
+            .join("\n\n");
+          if (detail) {
+            entries.push({
+              ...entry,
+              userInputSummary: submittedAnswers.map(({ answer }) => answer).join("; "),
+              detail: [detail, entry.detail].filter(Boolean).join("\n\n"),
+            });
+            continue;
+          }
+        }
+      }
+    }
+    entries.push(entry);
   }
   return collapseDerivedWorkLogEntries(entries);
 }