diff --git a/webview-ui/src/components/chat/ChatView.tsx b/webview-ui/src/components/chat/ChatView.tsx
index 89c4209b96d..e58e45ae9c2 100644
--- a/webview-ui/src/components/chat/ChatView.tsx
+++ b/webview-ui/src/components/chat/ChatView.tsx
@@ -44,6 +44,7 @@ import SystemPromptWarning from "./SystemPromptWarning"
 import ProfileViolationWarning from "./ProfileViolationWarning"
 import { CheckpointWarning } from "./CheckpointWarning"
 import { QueuedMessages } from "./QueuedMessages"
+import StickyUserMessageNav from "./StickyUserMessageNav"
 import DismissibleUpsell from "../common/DismissibleUpsell"
 import { useCloudUpsell } from "@src/hooks/useCloudUpsell"
 import { Cloud } from "lucide-react"
@@ -150,6 +151,7 @@ const ChatViewComponent: React.ForwardRefRenderFunction<ChatViewRef, ChatViewPro
 	const stickyFollowRef = useRef<boolean>(false)
 	const [showScrollToBottom, setShowScrollToBottom] = useState(false)
 	const [isAtBottom, setIsAtBottom] = useState(false)
+	const [firstVisibleIndex, setFirstVisibleIndex] = useState(0)
 	const lastTtsRef = useRef<string>("")
 	const [wasStreaming, setWasStreaming] = useState<boolean>(false)
 	const [checkpointWarning, setCheckpointWarning] = useState<
@@ -1113,6 +1115,46 @@ const ChatViewComponent: React.ForwardRefRenderFunction<ChatViewRef, ChatViewPro
 		return result
 	}, [isCondensing, visibleMessages, isBrowserSessionMessage])
 
+	// Compute user message indices from groupedMessages for sticky navigation
+	const userMessageIndices = useMemo(() => {
+		const indices: number[] = []
+		groupedMessages.forEach((msg, index) => {
+			if (msg.say === "user_feedback") {
+				indices.push(index)
+			}
+		})
+		return indices
+	}, [groupedMessages])
+
+	// Find the last user message that is scrolled out of view (before firstVisibleIndex)
+	const stickyNavMessage = useMemo(() => {
+		// Find the last user message index that is before the first visible index
+		const lastUserIndexBeforeVisible = userMessageIndices.findLast((idx) => idx < firstVisibleIndex)
+		if (lastUserIndexBeforeVisible !== undefined) {
+			return groupedMessages[lastUserIndexBeforeVisible]
+		}
+		return null
+	}, [userMessageIndices, firstVisibleIndex, groupedMessages])
+
+	// Show sticky nav when user has scrolled up past a user message and not at top
+	const showStickyNav = useMemo(() => {
+		return stickyNavMessage !== null && firstVisibleIndex > 0 && !isAtBottom
+	}, [stickyNavMessage, firstVisibleIndex, isAtBottom])
+
+	// Handler to scroll to the sticky nav message
+	const handleStickyNavClick = useCallback(() => {
+		if (stickyNavMessage) {
+			const messageIndex = groupedMessages.findIndex((msg) => msg.ts === stickyNavMessage.ts)
+			if (messageIndex >= 0) {
+				virtuosoRef.current?.scrollToIndex({
+					index: messageIndex,
+					behavior: "smooth",
+					align: "start",
+				})
+			}
+		}
+	}, [stickyNavMessage, groupedMessages])
+
 	// scrolling
 
 	const scrollToBottomSmooth = useMemo(
@@ -1490,7 +1532,12 @@ const ChatViewComponent: React.ForwardRefRenderFunction<ChatViewRef, ChatViewPro
 
 			{task && (
 				<>
-					<div className="grow flex" ref={scrollContainerRef}>
+					<div className="grow flex flex-col relative" ref={scrollContainerRef}>
+						<StickyUserMessageNav
+							message={stickyNavMessage}
+							onNavigate={handleStickyNavClick}
+							isVisible={showStickyNav}
+						/>
 						<Virtuoso
 							ref={virtuosoRef}
 							key={task.ts}
@@ -1506,6 +1553,9 @@ const ChatViewComponent: React.ForwardRefRenderFunction<ChatViewRef, ChatViewPro
 							}}
 							atBottomThreshold={10}
 							initialTopMostItemIndex={groupedMessages.length - 1}
+							rangeChanged={(range) => {
+								setFirstVisibleIndex(range.startIndex)
+							}}
 						/>
 					</div>
 					{areButtonsVisible && (
diff --git a/webview-ui/src/components/chat/StickyUserMessageNav.tsx b/webview-ui/src/components/chat/StickyUserMessageNav.tsx
new file mode 100644
index 00000000000..baf5948909a
--- /dev/null
+++ b/webview-ui/src/components/chat/StickyUserMessageNav.tsx
@@ -0,0 +1,63 @@
+import React, { memo } from "react"
+import { useTranslation } from "react-i18next"
+import { ChevronUp, User } from "lucide-react"
+import type { ClineMessage } from "@roo-code/types"
+import { cn } from "@/lib/utils"
+
+interface StickyUserMessageNavProps {
+	/** The user message to display in the sticky nav */
+	message: ClineMessage | null
+	/** Callback when the sticky nav is clicked to scroll to the message */
+	onNavigate: () => void
+	/** Whether the sticky nav should be visible */
+	isVisible: boolean
+}
+
+/**
+ * A sticky navigation component that appears at the top of the chat when the user
+ * scrolls up past their messages. Clicking it scrolls back to the most recent
+ * user message that is out of view.
+ */
+const StickyUserMessageNav = memo(({ message, onNavigate, isVisible }: StickyUserMessageNavProps) => {
+	const { t } = useTranslation()
+
+	if (!isVisible || !message) {
+		return null
+	}
+
+	// Truncate message text for display
+	const displayText = message.text || ""
+	const truncatedText = displayText.length > 80 ? displayText.substring(0, 80) + "..." : displayText
+
+	return (
+		<div
+			className={cn(
+				"sticky top-0 z-10 flex items-center gap-2 px-3 py-2 cursor-pointer",
+				"bg-vscode-editor-background/95 backdrop-blur-sm",
+				"border-b border-vscode-editorGroup-border",
+				"transition-all duration-200 ease-in-out",
+				"hover:bg-vscode-list-hoverBackground",
+			)}
+			onClick={onNavigate}
+			role="button"
+			tabIndex={0}
+			onKeyDown={(e) => {
+				if (e.key === "Enter" || e.key === " ") {
+					e.preventDefault()
+					onNavigate()
+				}
+			}}
+			aria-label={t("chat:stickyNav.scrollToMessage")}>
+			<ChevronUp className="w-4 h-4 text-vscode-descriptionForeground shrink-0" />
+			<User className="w-4 h-4 text-vscode-descriptionForeground shrink-0" />
+			<span className="text-sm text-vscode-foreground truncate flex-1">{truncatedText}</span>
+			<span className="text-xs text-vscode-descriptionForeground shrink-0">
+				{t("chat:stickyNav.clickToJump")}
+			</span>
+		</div>
+	)
+})
+
+StickyUserMessageNav.displayName = "StickyUserMessageNav"
+
+export default StickyUserMessageNav
diff --git a/webview-ui/src/i18n/locales/en/chat.json b/webview-ui/src/i18n/locales/en/chat.json
index 9ce1ea34318..bf69695870f 100644
--- a/webview-ui/src/i18n/locales/en/chat.json
+++ b/webview-ui/src/i18n/locales/en/chat.json
@@ -477,5 +477,9 @@
 		"updated": "Updated the to-do list",
 		"completed": "Completed",
 		"started": "Started"
+	},
+	"stickyNav": {
+		"scrollToMessage": "Scroll to your message",
+		"clickToJump": "Click to jump"
 	}
 }