diff --git a/site/src/pages/AgentsPage/components/AgentDetailView.stories.tsx b/site/src/pages/AgentsPage/components/AgentDetailView.stories.tsx
index f8f56afddc..28b86d8680 100644
--- a/site/src/pages/AgentsPage/components/AgentDetailView.stories.tsx
+++ b/site/src/pages/AgentsPage/components/AgentDetailView.stories.tsx
@@ -1,6 +1,6 @@
 import { MockUserOwner } from "testHelpers/entities";
 import { withAuthProvider, withDashboardProvider } from "testHelpers/storybook";
-import type { Meta, StoryObj } from "@storybook/react-vite";
+import type { Decorator, Meta, StoryObj } from "@storybook/react-vite";
 import { API } from "api/api";
 import type * as TypesGen from "api/typesGenerated";
 import type { ChatDiffStatus, ChatMessagePart } from "api/typesGenerated";
@@ -453,25 +453,44 @@ const buildLongConversation = (count: number): TypesGen.ChatMessage[] => {
 	return messages;
 };
 
+const scrollStoryDecorators: Decorator[] = [
+	(Story) => (
+		<div
+			style={{
+				height: "600px",
+				display: "flex",
+				flexDirection: "column",
+			}}
+		>
+			<Story />
+		</div>
+	),
+];
+
+const waitForScrollOverflow = async (scrollContainer: HTMLElement) => {
+	await waitFor(() => {
+		expect(scrollContainer.scrollHeight).toBeGreaterThan(
+			scrollContainer.clientHeight,
+		);
+	});
+};
+
+const scrollAwayFromBottom = (scrollContainer: HTMLElement) => {
+	const maxScroll = scrollContainer.scrollHeight - scrollContainer.clientHeight;
+	scrollContainer.scrollTop = -maxScroll;
+	if (Math.abs(scrollContainer.scrollTop) < 100) {
+		scrollContainer.scrollTop = maxScroll;
+	}
+	scrollContainer.dispatchEvent(new Event("scroll"));
+};
+
 /** Scroll-to-bottom button appears after scrolling up in a long
  *  conversation, and clicking it returns to the bottom. */
 export const ScrollToBottomButton: Story = {
 	args: {
 		store: buildStoreWithMessages(buildLongConversation(40)),
 	},
-	decorators: [
-		(Story) => (
-			<div
-				style={{
-					height: "600px",
-					display: "flex",
-					flexDirection: "column",
-				}}
-			>
-				<Story />
-			</div>
-		),
-	],
+	decorators: scrollStoryDecorators,
 	play: async ({ canvasElement }) => {
 		const canvas = within(canvasElement);
 
@@ -485,23 +504,13 @@ export const ScrollToBottomButton: Story = {
 		const scrollContainer = canvas.getByTestId("scroll-container");
 
 		// Wait for content to render and create overflow.
-		await waitFor(() => {
-			expect(scrollContainer.scrollHeight).toBeGreaterThan(
-				scrollContainer.clientHeight,
-			);
-		});
+		await waitForScrollOverflow(scrollContainer);
 
 		// Scroll up. In flex-col-reverse containers, Chrome uses
 		// negative scrollTop values when scrolled away from the
 		// bottom. Try negative first, fall back to positive for
 		// other engines.
-		const maxScroll =
-			scrollContainer.scrollHeight - scrollContainer.clientHeight;
-		scrollContainer.scrollTop = -maxScroll;
-		if (Math.abs(scrollContainer.scrollTop) < 100) {
-			scrollContainer.scrollTop = maxScroll;
-		}
-		scrollContainer.dispatchEvent(new Event("scroll"));
+		scrollAwayFromBottom(scrollContainer);
 
 		// Button should become visible (enters the accessibility tree).
 		const button = await waitFor(() => {
@@ -522,3 +531,129 @@ export const ScrollToBottomButton: Story = {
 		});
 	},
 };
+
+/** When scrolled away from bottom, new content preserves scroll position. */
+export const ScrollPositionPreservedOnNewContent: Story = {
+	args: {
+		store: buildStoreWithMessages(buildLongConversation(30)),
+	},
+	decorators: scrollStoryDecorators,
+	play: async ({ canvasElement, args }) => {
+		const canvas = within(canvasElement);
+		const scrollContainer = canvas.getByTestId("scroll-container");
+
+		await waitForScrollOverflow(scrollContainer);
+
+		// Scroll away from bottom.
+		scrollAwayFromBottom(scrollContainer);
+
+		// Wait for the button to confirm we are away from the bottom.
+		await waitFor(
+			() => {
+				expect(
+					canvas.getByRole("button", { name: "Scroll to bottom" }),
+				).toBeVisible();
+			},
+			{ timeout: 2000 },
+		);
+
+		// Record position while clearly away from the bottom.
+		const scrollTopBefore = scrollContainer.scrollTop;
+		expect(Math.abs(scrollTopBefore)).toBeGreaterThan(50);
+
+		const store = args?.store;
+		if (!store) {
+			throw new Error("Expected store in args");
+		}
+
+		const snapshot = store.getSnapshot();
+		const existing: TypesGen.ChatMessage[] = [];
+		for (const id of snapshot.orderedMessageIDs) {
+			const message = snapshot.messagesByID.get(id);
+			if (message) {
+				existing.push(message);
+			}
+		}
+
+		const newMessages = [
+			buildMessage(31, "user", "Follow-up question about the implementation."),
+			buildMessage(
+				32,
+				"assistant",
+				"Here is a detailed response about the implementation details you asked about.",
+			),
+		];
+		store.replaceMessages(existing.concat(newMessages));
+
+		// Wait for ResizeObserver + RAF compensation to settle.
+		// We should remain significantly away from the bottom.
+		await waitFor(
+			() => {
+				expect(Math.abs(scrollContainer.scrollTop)).toBeGreaterThan(50);
+			},
+			{ timeout: 2000 },
+		);
+
+		expect(
+			canvas.getByRole("button", { name: "Scroll to bottom" }),
+		).toBeVisible();
+	},
+};
+
+/** When at bottom, new content keeps the user pinned to bottom. */
+export const ScrollPinnedToBottomOnNewContent: Story = {
+	args: {
+		store: buildStoreWithMessages(buildLongConversation(30)),
+	},
+	decorators: scrollStoryDecorators,
+	play: async ({ canvasElement, args }) => {
+		const canvas = within(canvasElement);
+		const scrollContainer = canvas.getByTestId("scroll-container");
+
+		await waitForScrollOverflow(scrollContainer);
+
+		// Verify the starting position is pinned to the bottom.
+		expect(Math.abs(scrollContainer.scrollTop)).toBeLessThan(5);
+		expect(
+			canvas.queryByRole("button", { name: "Scroll to bottom" }),
+		).toBeNull();
+
+		const store = args?.store;
+		if (!store) {
+			throw new Error("Expected store in args");
+		}
+
+		const snapshot = store.getSnapshot();
+		const existing: TypesGen.ChatMessage[] = [];
+		for (const id of snapshot.orderedMessageIDs) {
+			const message = snapshot.messagesByID.get(id);
+			if (message) {
+				existing.push(message);
+			}
+		}
+
+		const newMessages = [
+			buildMessage(31, "user", "Another question."),
+			buildMessage(32, "assistant", "Here is the answer with full details."),
+			buildMessage(33, "user", "Thanks, one more thing."),
+			buildMessage(
+				34,
+				"assistant",
+				"Sure, here is the additional information you requested.",
+			),
+		];
+		store.replaceMessages(existing.concat(newMessages));
+
+		// Wait for the double-RAF pin to complete.
+		await waitFor(
+			() => {
+				expect(Math.abs(scrollContainer.scrollTop)).toBeLessThan(5);
+			},
+			{ timeout: 2000 },
+		);
+
+		expect(
+			canvas.queryByRole("button", { name: "Scroll to bottom" }),
+		).toBeNull();
+	},
+};
diff --git a/site/src/pages/AgentsPage/components/AgentDetailView.tsx b/site/src/pages/AgentsPage/components/AgentDetailView.tsx
index 00a088c357..bafb5fb1b8 100644
--- a/site/src/pages/AgentsPage/components/AgentDetailView.tsx
+++ b/site/src/pages/AgentsPage/components/AgentDetailView.tsx
@@ -503,13 +503,29 @@ export const AgentDetailNotFoundView: FC<AgentDetailNotFoundViewProps> = ({
 
 /**
  * Scroll container that uses flex-col-reverse for bottom-anchored chat
- * layout. Handles loading older message pages via an IntersectionObserver
- * sentinel and manually restores scroll position after new content
- * renders — CSS scroll anchoring is unreliable in flex-col-reverse
- * containers.
+ * layout. In this layout scrollTop = 0 means the user is at the
+ * bottom (most recent content); scrolling up moves scrollTop away from
+ * 0 (negative in Chrome, positive in Firefox).
+ *
+ * Handles:
+ * - Loading older message pages via an IntersectionObserver sentinel.
+ * - ResizeObserver-driven scroll anchoring for transcript and viewport
+ *   size changes.
+ * - A floating "Scroll to bottom" button when the user is scrolled
+ *   away from the bottom.
+ *
+ * CSS scroll anchoring is unreliable in flex-col-reverse containers,
+ * so all position restoration is done manually.
  */
 const SCROLL_THRESHOLD = 100;
 
+// In flex-col-reverse, scrollTop is 0 at the bottom. Its sign
+// when scrolled up varies by engine (negative in Chrome, positive
+// in Firefox). The user is "near bottom" when close to 0.
+function isNearBottom(container: HTMLElement): boolean {
+	return Math.abs(container.scrollTop) < SCROLL_THRESHOLD;
+}
+
 const ScrollAnchoredContainer: FC<{
 	scrollContainerRef: RefObject<HTMLDivElement | null>;
 	isFetchingMoreMessages: boolean;
@@ -527,6 +543,13 @@ const ScrollAnchoredContainer: FC<{
 	const observerRef = useRef<IntersectionObserver | null>(null);
 	const isFetchingRef = useRef(isFetchingMoreMessages);
 	const onFetchRef = useRef(onFetchMoreMessages);
+	const autoScrollRef = useRef(true);
+	const contentRef = useRef<HTMLDivElement>(null);
+	// Guard flag: true while a programmatic scroll adjustment is in-flight.
+	// The scroll handler skips autoScrollRef updates and re-render triggers
+	// when this is set, preventing user-visible jitter. Cleared when the
+	// scroll reaches its destination or the user actively interrupts.
+	const isRestoringScrollRef = useRef(false);
 	useEffect(() => {
 		isFetchingRef.current = isFetchingMoreMessages;
 		onFetchRef.current = onFetchMoreMessages;
@@ -576,13 +599,164 @@ const ScrollAnchoredContainer: FC<{
 		observer.observe(sentinel);
 	}, [isFetchingMoreMessages]);
 
+	useEffect(() => {
+		const container = scrollContainerRef.current;
+		const content = contentRef.current;
+		if (!container || !content) return;
+
+		const initialContentRect = content.getBoundingClientRect();
+		let prevContentHeight = initialContentRect.height;
+		let prevContentWidth = initialContentRect.width;
+		let pinOuterRafId: number | null = null;
+		let pinInnerRafId: number | null = null;
+		let restoreGuardRafId: number | null = null;
+
+		const cancelPendingPins = () => {
+			if (pinOuterRafId !== null) {
+				cancelAnimationFrame(pinOuterRafId);
+			}
+			if (pinInnerRafId !== null) {
+				cancelAnimationFrame(pinInnerRafId);
+			}
+			pinOuterRafId = null;
+			pinInnerRafId = null;
+		};
+
+		const scheduleBottomPin = () => {
+			cancelPendingPins();
+			isRestoringScrollRef.current = true;
+			// Double-RAF lets React's commit phase and the browser's
+			// layout pass both complete before we pin to bottom.
+			pinOuterRafId = requestAnimationFrame(() => {
+				pinOuterRafId = null;
+				pinInnerRafId = requestAnimationFrame(() => {
+					pinInnerRafId = null;
+					if (!autoScrollRef.current) {
+						isRestoringScrollRef.current = false;
+						return;
+					}
+					if (restoreGuardRafId !== null) {
+						cancelAnimationFrame(restoreGuardRafId);
+					}
+					container.scrollTop = 0;
+					restoreGuardRafId = requestAnimationFrame(() => {
+						isRestoringScrollRef.current = false;
+						restoreGuardRafId = null;
+					});
+				});
+			});
+		};
+
+		const compensateScroll = (delta: number) => {
+			if (restoreGuardRafId !== null) {
+				cancelAnimationFrame(restoreGuardRafId);
+			}
+			isRestoringScrollRef.current = true;
+			// In flex-col-reverse, "away from bottom" can be either
+			// negative (Chrome) or positive (Firefox). Detect which
+			// convention applies and compensate accordingly.
+			if (container.scrollTop < 0) {
+				// Negative convention: subtract to move away from 0 (bottom).
+				container.scrollTop -= delta;
+			} else {
+				// Positive convention: add to move away from 0 (bottom).
+				container.scrollTop += delta;
+			}
+			restoreGuardRafId = requestAnimationFrame(() => {
+				isRestoringScrollRef.current = false;
+				restoreGuardRafId = null;
+			});
+		};
+
+		const observer = new ResizeObserver((entries) => {
+			const entry = entries[0];
+			const nextHeight =
+				entry?.contentRect.height ?? content.getBoundingClientRect().height;
+			const nextWidth =
+				entry?.contentRect.width ?? content.getBoundingClientRect().width;
+			const delta = nextHeight - prevContentHeight;
+			const widthChanged = Math.abs(nextWidth - prevContentWidth) > 1;
+			prevContentHeight = nextHeight;
+			prevContentWidth = nextWidth;
+			if (Math.abs(delta) < 1) {
+				return;
+			}
+
+			// Skip compensation during pagination. Older messages are
+			// prepended in flex-col-reverse which grows content into the
+			// overflow direction; the browser preserves scrollTop for us.
+			if (isFetchingRef.current) {
+				return;
+			}
+
+			// Skip compensation during reflow. Width changes indicate the
+			// height delta is distributed through the transcript rather than
+			// appended at the bottom, so applying the full delta would
+			// overcompensate and jump the user.
+			if (widthChanged) {
+				return;
+			}
+
+			if (autoScrollRef.current) {
+				scheduleBottomPin();
+				return;
+			}
+
+			compensateScroll(delta);
+		});
+		observer.observe(content);
+
+		return () => {
+			observer.disconnect();
+			cancelPendingPins();
+			if (restoreGuardRafId !== null) {
+				cancelAnimationFrame(restoreGuardRafId);
+			}
+			isRestoringScrollRef.current = false;
+		};
+	}, [scrollContainerRef]);
+
+	useEffect(() => {
+		const container = scrollContainerRef.current;
+		if (!container) return;
+
+		let prevContainerHeight = container.clientHeight;
+		let restoreGuardRafId: number | null = null;
+
+		const observer = new ResizeObserver((entries) => {
+			const nextHeight =
+				entries[0]?.contentRect.height ?? container.clientHeight;
+			const delta = nextHeight - prevContainerHeight;
+			prevContainerHeight = nextHeight;
+			if (Math.abs(delta) < 1 || !autoScrollRef.current) {
+				return;
+			}
+
+			if (restoreGuardRafId !== null) {
+				cancelAnimationFrame(restoreGuardRafId);
+			}
+			isRestoringScrollRef.current = true;
+			container.scrollTop = 0;
+			restoreGuardRafId = requestAnimationFrame(() => {
+				isRestoringScrollRef.current = false;
+				restoreGuardRafId = null;
+			});
+		});
+		observer.observe(container);
+
+		return () => {
+			observer.disconnect();
+			if (restoreGuardRafId !== null) {
+				cancelAnimationFrame(restoreGuardRafId);
+			}
+			isRestoringScrollRef.current = false;
+		};
+	}, [scrollContainerRef]);
+
 	// Track scroll position to show/hide the scroll-to-bottom button.
 	// In a flex-col-reverse container, scrollTop = 0 means the user
-	// is at the bottom (most recent content). Scrolling up to see
-	// older messages makes scrollTop negative.
-	//
-	// Throttled to once per animation frame so we avoid calling
-	// setState on every high-frequency scroll event.
+	// is at the bottom (most recent content). Scrolling up moves
+	// scrollTop away from 0, with the sign varying by engine.
 	useEffect(() => {
 		const container = scrollContainerRef.current;
 		if (!container) return;
@@ -590,19 +764,51 @@ const ScrollAnchoredContainer: FC<{
 		let rafId: number | null = null;
 
 		const handleScroll = () => {
+			// While a programmatic scroll is in progress (e.g. smooth
+			// scroll-to-bottom), suppress normal handling. Clear the
+			// guard once the scroll reaches the bottom so normal
+			// tracking resumes. User-input interruptions are handled
+			// separately via wheel/touchstart listeners.
+			if (isRestoringScrollRef.current) {
+				if (isNearBottom(container)) {
+					isRestoringScrollRef.current = false;
+					autoScrollRef.current = true;
+				}
+				return;
+			}
+
+			const nearBottom = isNearBottom(container);
+			autoScrollRef.current = nearBottom;
+
+			// Throttle the button visibility state update to once per
+			// frame. This is the only part that triggers a re-render.
 			if (rafId !== null) return;
 			rafId = requestAnimationFrame(() => {
-				const shouldShow = Math.abs(container.scrollTop) >= SCROLL_THRESHOLD;
-				setShowScrollToBottom((prev) =>
-					prev === shouldShow ? prev : shouldShow,
-				);
+				setShowScrollToBottom((prev) => {
+					const shouldShow = !isNearBottom(container);
+					return prev === shouldShow ? prev : shouldShow;
+				});
 				rafId = null;
 			});
 		};
 
+		const handleUserInterrupt = () => {
+			if (isRestoringScrollRef.current) {
+				isRestoringScrollRef.current = false;
+			}
+		};
+
 		container.addEventListener("scroll", handleScroll, { passive: true });
+		container.addEventListener("wheel", handleUserInterrupt, {
+			passive: true,
+		});
+		container.addEventListener("touchstart", handleUserInterrupt, {
+			passive: true,
+		});
 		return () => {
 			container.removeEventListener("scroll", handleScroll);
+			container.removeEventListener("wheel", handleUserInterrupt);
+			container.removeEventListener("touchstart", handleUserInterrupt);
 			if (rafId !== null) {
 				cancelAnimationFrame(rafId);
 			}
@@ -612,9 +818,11 @@ const ScrollAnchoredContainer: FC<{
 	const handleScrollToBottom = () => {
 		const container = scrollContainerRef.current;
 		if (!container) return;
+		autoScrollRef.current = true;
+		isRestoringScrollRef.current = true;
 		container.scrollTo({ top: 0, behavior: "smooth" });
 		// Hide immediately so the button doesn't linger while the
-		// smooth scroll animates.  If the user interrupts the scroll
+		// smooth scroll animates. If the user interrupts the scroll
 		// before it reaches the bottom, the scroll handler will
 		// re-show the button.
 		setShowScrollToBottom(false);
@@ -627,7 +835,7 @@ const ScrollAnchoredContainer: FC<{
 				data-testid="scroll-container"
 				className="flex min-h-0 flex-1 flex-col-reverse overflow-y-auto [overflow-anchor:none] [scrollbar-gutter:stable] [scrollbar-width:thin] [scrollbar-color:hsl(var(--surface-quaternary))_transparent]"
 			>
-				{children}
+				<div ref={contentRef}>{children}</div>
 				{hasMoreMessages && <div ref={sentinelRef} className="h-px shrink-0" />}
 			</div>
 			<div className="pointer-events-none absolute inset-x-0 bottom-2 z-10 flex justify-center overflow-y-auto py-2 [scrollbar-gutter:stable] [scrollbar-width:thin]">