diff --git a/apps/web/src/components/ChatView.tsx b/apps/web/src/components/ChatView.tsx
index 25ed763952..ee922c291d 100644
--- a/apps/web/src/components/ChatView.tsx
+++ b/apps/web/src/components/ChatView.tsx
@@ -91,6 +91,7 @@ import { useTheme } from "../hooks/useTheme";
 import { useTurnDiffSummaries } from "../hooks/useTurnDiffSummaries";
 import { BranchToolbar } from "./BranchToolbar";
 import { resolveShortcutCommand, shortcutLabelForCommand } from "../keybindings";
+import { ChatOutlinePanel } from "./chat/ChatOutlinePanel";
 import PlanSidebar from "./PlanSidebar";
 import ThreadTerminalDrawer from "./ThreadTerminalDrawer";
 import { ChevronDownIcon } from "lucide-react";
@@ -694,6 +695,7 @@ export default function ChatView(props: ChatViewProps) {
   );
   const messagesScrollRef = useRef<HTMLDivElement>(null);
   const [messagesScrollElement, setMessagesScrollElement] = useState<HTMLDivElement | null>(null);
+  const scrollToMessageRef = useRef<((messageId: string) => void) | null>(null);
   const shouldAutoScrollRef = useRef(true);
   const lastKnownScrollTopRef = useRef(0);
   const isPointerScrollActiveRef = useRef(false);
@@ -3330,7 +3332,7 @@ export default function ChatView(props: ChatViewProps) {
       {/* Main content area with optional plan sidebar */}
       <div className="flex min-h-0 min-w-0 flex-1">
         {/* Chat column */}
-        <div className="flex min-h-0 min-w-0 flex-1 flex-col">
+        <div className="relative flex min-h-0 min-w-0 flex-1 flex-col">
           {/* Messages Wrapper */}
           <div className="relative flex min-h-0 flex-1 flex-col">
             {/* Messages */}
@@ -3375,9 +3377,17 @@ export default function ChatView(props: ChatViewProps) {
                 resolvedTheme={resolvedTheme}
                 timestampFormat={timestampFormat}
                 workspaceRoot={activeWorkspaceRoot}
+                onScrollToMessageRef={scrollToMessageRef}
               />
             </div>
 
+            {/* Chat outline strip — aligned to right edge of message content */}
+            <ChatOutlinePanel
+              timelineEntries={timelineEntries}
+              scrollContainer={messagesScrollElement}
+              onScrollToMessage={scrollToMessageRef}
+            />
+
             {/* scroll to bottom pill — shown when user has scrolled away from the bottom */}
             {showScrollToBottom && (
               <div className="pointer-events-none absolute bottom-1 left-1/2 z-30 flex -translate-x-1/2 justify-center py-1.5">
diff --git a/apps/web/src/components/chat/ChatOutlinePanel.tsx b/apps/web/src/components/chat/ChatOutlinePanel.tsx
new file mode 100644
index 0000000000..7d6c3e9841
--- /dev/null
+++ b/apps/web/src/components/chat/ChatOutlinePanel.tsx
@@ -0,0 +1,230 @@
+/**
+ * Minimap-style outline strip beside the chat content.
+ * Shows a small bar per user message; hover to expand a popover with previews.
+ * Click any bar or preview to scroll to that message.
+ *
+ * Uses MutationObserver + IntersectionObserver to handle @tanstack/react-virtual
+ * row mount/unmount — elements are tracked as the virtualizer creates them.
+ */
+import { memo, useCallback, useEffect, useMemo, useRef, useState } from "react";
+import { UserIcon } from "lucide-react";
+import type { TimelineEntry } from "../../session-logic";
+
+interface OutlineEntry {
+  readonly id: string;
+  readonly preview: string;
+}
+
+interface ChatOutlinePanelProps {
+  readonly timelineEntries: ReadonlyArray<TimelineEntry>;
+  readonly scrollContainer: HTMLDivElement | null;
+  readonly onScrollToMessage: React.MutableRefObject<((messageId: string) => void) | null>;
+}
+
+export const ChatOutlinePanel = memo(function ChatOutlinePanel({
+  timelineEntries,
+  scrollContainer,
+  onScrollToMessage,
+}: ChatOutlinePanelProps) {
+  const outlineEntries = useMemo(
+    () =>
+      timelineEntries
+        .filter(
+          (e): e is TimelineEntry & { kind: "message" } => e.kind === "message",
+        )
+        .filter((e) => e.message.role === "user")
+        .map((e) => ({
+          id: e.message.id,
+          preview: e.message.text.split("\n")[0]?.slice(0, 80) ?? "",
+        })),
+    [timelineEntries],
+  );
+
+  // Active message tracking — MutationObserver watches for virtualizer
+  // mount/unmount, IntersectionObserver tracks visibility.
+  const [activeMessageIds, setActiveMessageIds] = useState<ReadonlySet<string>>(
+    () => new Set<string>(),
+  );
+
+  useEffect(() => {
+    if (!scrollContainer) return;
+
+    const intersectionObserver = new IntersectionObserver(
+      (entries) => {
+        setActiveMessageIds((prev) => {
+          let changed = false;
+          const next = new Set(prev);
+          for (const entry of entries) {
+            const id = (entry.target as HTMLElement).dataset.messageId;
+            if (!id) continue;
+            const sizeBefore = next.size;
+            if (entry.isIntersecting) {
+              next.add(id);
+            } else {
+              next.delete(id);
+            }
+            if (next.size !== sizeBefore) changed = true;
+          }
+          return changed ? next : prev;
+        });
+      },
+      { root: scrollContainer, threshold: 0.1 },
+    );
+
+    // Observe any user-message element currently in the DOM
+    const observeUserMessages = (root: Element) => {
+      root.querySelectorAll('[data-message-role="user"]').forEach((el) => {
+        intersectionObserver.observe(el);
+      });
+    };
+
+    // Initial pass for elements already rendered
+    observeUserMessages(scrollContainer);
+
+    // Watch for virtualizer adding/removing rows
+    const mutationObserver = new MutationObserver((mutations) => {
+      const removedIds: string[] = [];
+      for (const mutation of mutations) {
+        for (const node of mutation.addedNodes) {
+          if (!(node instanceof HTMLElement)) continue;
+          if (node.dataset.messageRole === "user") {
+            intersectionObserver.observe(node);
+          } else {
+            observeUserMessages(node);
+          }
+        }
+        for (const node of mutation.removedNodes) {
+          if (!(node instanceof HTMLElement)) continue;
+          // Check the node itself and nested children for message IDs
+          const id = node.dataset.messageId;
+          if (id) {
+            removedIds.push(id);
+          } else {
+            node.querySelectorAll("[data-message-id]").forEach((el) => {
+              const nestedId = (el as HTMLElement).dataset.messageId;
+              if (nestedId) removedIds.push(nestedId);
+            });
+          }
+        }
+      }
+      if (removedIds.length > 0) {
+        setActiveMessageIds((prev) => {
+          const next = new Set(prev);
+          for (const id of removedIds) next.delete(id);
+          return next;
+        });
+      }
+    });
+
+    mutationObserver.observe(scrollContainer, { childList: true, subtree: true });
+
+    return () => {
+      intersectionObserver.disconnect();
+      mutationObserver.disconnect();
+    };
+  }, [scrollContainer]);
+
+  // Scroll to message via virtualizer (works for all messages, including off-screen)
+  const handleClick = useCallback(
+    (e: React.MouseEvent<HTMLButtonElement>) => {
+      const messageId = e.currentTarget.dataset.outlineId;
+      if (!messageId) return;
+      // Use virtualizer scrollToIndex — handles off-screen virtualized rows
+      if (onScrollToMessage.current) {
+        onScrollToMessage.current(messageId);
+        return;
+      }
+      // Fallback: querySelector for elements currently in DOM
+      if (!scrollContainer) return;
+      const el = scrollContainer.querySelector(
+        `[data-message-id="${CSS.escape(messageId)}"]`,
+      );
+      if (el) {
+        el.scrollIntoView({ behavior: "smooth", block: "center" });
+      }
+    },
+    [onScrollToMessage, scrollContainer],
+  );
+
+  // Hover state — shows expanded popover
+  const [isHovered, setIsHovered] = useState(false);
+  const hoverTimerRef = useRef<ReturnType<typeof setTimeout> | null>(null);
+
+  const handleMouseEnter = useCallback(() => {
+    if (hoverTimerRef.current) {
+      clearTimeout(hoverTimerRef.current);
+      hoverTimerRef.current = null;
+    }
+    setIsHovered(true);
+  }, []);
+
+  const handleMouseLeave = useCallback(() => {
+    hoverTimerRef.current = setTimeout(() => {
+      setIsHovered(false);
+    }, 200);
+  }, []);
+
+  useEffect(() => {
+    return () => {
+      if (hoverTimerRef.current) {
+        clearTimeout(hoverTimerRef.current);
+      }
+    };
+  }, []);
+
+  if (outlineEntries.length === 0) {
+    return null;
+  }
+
+  return (
+    <div
+      className="pointer-events-none absolute top-0 z-30"
+      style={{ left: "calc(50% + 24rem + 0.5rem)" }}
+      onMouseEnter={handleMouseEnter}
+      onMouseLeave={handleMouseLeave}
+    >
+      <div className="pointer-events-auto relative flex max-h-40 w-5 flex-col items-center gap-[5px] overflow-y-auto py-4">
+        {outlineEntries.map((entry) => (
+          <button
+            key={entry.id}
+            type="button"
+            data-outline-id={entry.id}
+            onClick={handleClick}
+            className={`h-[3px] w-4 shrink-0 rounded-full transition-colors ${
+              activeMessageIds.has(entry.id)
+                ? "bg-foreground/60"
+                : "bg-foreground/25"
+            } hover:bg-foreground/80`}
+          />
+        ))}
+      </div>
+
+      {isHovered ? (
+        <div
+          className="pointer-events-auto absolute top-0 right-full mr-2 w-56 rounded-md border border-border bg-popover p-1.5 shadow-lg"
+          onMouseEnter={handleMouseEnter}
+          onMouseLeave={handleMouseLeave}
+        >
+          <div className="max-h-72 overflow-y-auto">
+            {outlineEntries.map((entry) => (
+              <button
+                key={entry.id}
+                type="button"
+                data-outline-id={entry.id}
+                onClick={handleClick}
+                className={`flex w-full items-start gap-2 rounded px-2 py-1.5 text-left text-xs transition-colors hover:bg-accent/50 ${
+                  activeMessageIds.has(entry.id) ? "bg-accent/30" : ""
+                }`}
+              >
+                <UserIcon className="mt-0.5 h-3 w-3 shrink-0 text-muted-foreground" />
+                <span className="line-clamp-2 text-muted-foreground">
+                  {entry.preview || "(empty)"}
+                </span>
+              </button>
+            ))}
+          </div>
+        </div>
+      ) : null}
+    </div>
+  );
+});
diff --git a/apps/web/src/components/chat/MessagesTimeline.tsx b/apps/web/src/components/chat/MessagesTimeline.tsx
index f08d544cc1..2d7e8dbd8a 100644
--- a/apps/web/src/components/chat/MessagesTimeline.tsx
+++ b/apps/web/src/components/chat/MessagesTimeline.tsx
@@ -103,6 +103,7 @@ interface MessagesTimelineProps {
       end: number;
     }>;
   }) => void;
+  onScrollToMessageRef?: React.MutableRefObject<((messageId: string) => void) | null>;
 }
 
 export const MessagesTimeline = memo(function MessagesTimeline({
@@ -132,6 +133,7 @@ export const MessagesTimeline = memo(function MessagesTimeline({
   timestampFormat,
   workspaceRoot,
   onVirtualizerSnapshot,
+  onScrollToMessageRef,
 }: MessagesTimelineProps) {
   const timelineRootRef = useRef<HTMLDivElement | null>(null);
   const [timelineWidthPx, setTimelineWidthPx] = useState<number | null>(null);
@@ -259,6 +261,44 @@ export const MessagesTimeline = memo(function MessagesTimeline({
       rowVirtualizer.shouldAdjustScrollPositionOnItemSizeChange = undefined;
     };
   }, [rowVirtualizer]);
+
+  // Pre-computed message-id → row-index map for O(1) lookups
+  const messageIndexMap = useMemo(() => {
+    const map = new Map<string, number>();
+    rows.forEach((row, index) => {
+      if (row.kind === "message") {
+        map.set(row.message.id, index);
+      }
+    });
+    return map;
+  }, [rows]);
+
+  // Expose scroll-to-message for ChatOutlinePanel
+  useEffect(() => {
+    if (!onScrollToMessageRef) return;
+    onScrollToMessageRef.current = (messageId: string) => {
+      const index = messageIndexMap.get(messageId);
+      if (index === undefined) return;
+
+      // Tail rows (index >= virtualizedRowCount) are always in the DOM but not
+      // tracked by the virtualizer — use scrollIntoView for those.
+      if (index >= virtualizedRowCount) {
+        const el = scrollContainer?.querySelector(
+          `[data-message-id="${CSS.escape(messageId)}"]`,
+        );
+        if (el) {
+          el.scrollIntoView({ behavior: "smooth", block: "center" });
+        }
+        return;
+      }
+
+      rowVirtualizer.scrollToIndex(index, { align: "center" });
+    };
+    return () => {
+      onScrollToMessageRef.current = null;
+    };
+  }, [onScrollToMessageRef, messageIndexMap, rowVirtualizer, virtualizedRowCount, scrollContainer]);
+
   const pendingMeasureFrameRef = useRef<number | null>(null);
   const onTimelineImageLoad = useCallback(() => {
     if (pendingMeasureFrameRef.current !== null) return;