diff --git a/webview-ui/src/components/chat/ChatView.tsx b/webview-ui/src/components/chat/ChatView.tsx
index b6c3b0bdf0..ddf174aa74 100644
--- a/webview-ui/src/components/chat/ChatView.tsx
+++ b/webview-ui/src/components/chat/ChatView.tsx
@@ -1641,7 +1641,8 @@ const ChatViewComponent: React.ForwardRefRenderFunction<ChatViewRef, ChatViewPro
 		vscode.postMessage({ type: "condenseTaskContextRequest", text: taskId })
 	}
 
-	const areButtonsVisible = showScrollToBottom || primaryButtonText || secondaryButtonText
+	const hasApprovalButtons = Boolean(primaryButtonText || secondaryButtonText)
+	const areButtonsVisible = showScrollToBottom || hasApprovalButtons
 	const currentTaskAggregatedCosts = currentTaskId ? aggregatedCostsMap.get(currentTaskId) : undefined
 
 	return (
@@ -1735,17 +1736,23 @@ const ChatViewComponent: React.ForwardRefRenderFunction<ChatViewRef, ChatViewPro
 							className={`flex h-9 items-center mb-1 px-[15px] ${
 								showScrollToBottom ? "opacity-100" : enableButtons ? "opacity-100" : "opacity-50"
 							}`}>
-							{showScrollToBottom ? (
+							{showScrollToBottom && (
 								<>
 									<StandardTooltip content={t("chat:scrollToBottom")}>
 										<Button
 											variant="secondary"
-											className={hasLatestCheckpoint ? "flex-1 mr-[6px]" : "flex-[2]"}
+											className={
+												hasApprovalButtons
+													? "w-9 shrink-0 mr-[6px]"
+													: hasLatestCheckpoint
+														? "flex-1 mr-[6px]"
+														: "flex-[2]"
+											}
 											onClick={handleScrollToBottomAndResetCheckpointCursor}>
 											<span className="codicon codicon-chevron-down"></span>
 										</Button>
 									</StandardTooltip>
-									{hasLatestCheckpoint && (
+									{hasLatestCheckpoint && !hasApprovalButtons && (
 										<StandardTooltip content={t("chat:scrollToLatestCheckpoint")}>
 											<Button
 												variant="secondary"
@@ -1757,63 +1764,61 @@ const ChatViewComponent: React.ForwardRefRenderFunction<ChatViewRef, ChatViewPro
 										</StandardTooltip>
 									)}
 								</>
-							) : (
-								<>
-									{primaryButtonText && (
-										<StandardTooltip
-											content={
-												primaryButtonText === t("chat:retry.title")
-													? t("chat:retry.tooltip")
-													: primaryButtonText === t("chat:save.title")
-														? t("chat:save.tooltip")
-														: primaryButtonText === t("chat:approve.title")
-															? t("chat:approve.tooltip")
-															: primaryButtonText === t("chat:runCommand.title")
-																? t("chat:runCommand.tooltip")
-																: primaryButtonText === t("chat:startNewTask.title")
-																	? t("chat:startNewTask.tooltip")
-																	: primaryButtonText === t("chat:resumeTask.title")
-																		? t("chat:resumeTask.tooltip")
-																		: primaryButtonText ===
-																			  t("chat:proceedAnyways.title")
-																			? t("chat:proceedAnyways.tooltip")
-																			: primaryButtonText ===
-																				  t("chat:proceedWhileRunning.title")
-																				? t("chat:proceedWhileRunning.tooltip")
-																				: undefined
-											}>
-											<Button
-												variant="primary"
-												disabled={!enableButtons}
-												className={secondaryButtonText ? "flex-1 mr-[6px]" : "flex-[2] mr-0"}
-												onClick={() => handlePrimaryButtonClick(inputValue, selectedImages)}>
-												{primaryButtonText}
-											</Button>
-										</StandardTooltip>
-									)}
-									{secondaryButtonText && (
-										<StandardTooltip
-											content={
-												secondaryButtonText === t("chat:startNewTask.title")
-													? t("chat:startNewTask.tooltip")
-													: secondaryButtonText === t("chat:reject.title")
-														? t("chat:reject.tooltip")
-														: secondaryButtonText === t("chat:terminate.title")
-															? t("chat:terminate.tooltip")
-															: secondaryButtonText === t("chat:killCommand.title")
-																? t("chat:killCommand.tooltip")
-																: undefined
-											}>
-											<Button
-												variant="secondary"
-												disabled={!enableButtons}
-												className="flex-1 ml-[6px]"
-												onClick={() => handleSecondaryButtonClick(inputValue, selectedImages)}>
-												{secondaryButtonText}
-											</Button>
-										</StandardTooltip>
-									)}
-								</>
+							)}
+							{primaryButtonText && (
+								<StandardTooltip
+									content={
+										primaryButtonText === t("chat:retry.title")
+											? t("chat:retry.tooltip")
+											: primaryButtonText === t("chat:save.title")
+												? t("chat:save.tooltip")
+												: primaryButtonText === t("chat:approve.title")
+													? t("chat:approve.tooltip")
+													: primaryButtonText === t("chat:runCommand.title")
+														? t("chat:runCommand.tooltip")
+														: primaryButtonText === t("chat:startNewTask.title")
+															? t("chat:startNewTask.tooltip")
+															: primaryButtonText === t("chat:resumeTask.title")
+																? t("chat:resumeTask.tooltip")
+																: primaryButtonText === t("chat:proceedAnyways.title")
+																	? t("chat:proceedAnyways.tooltip")
+																	: primaryButtonText ===
+																		  t("chat:proceedWhileRunning.title")
+																		? t("chat:proceedWhileRunning.tooltip")
+																		: primaryButtonText
+									}>
+									<Button
+										variant="primary"
+										disabled={!enableButtons}
+										className={
+											secondaryButtonText ? "min-w-0 flex-1 mr-[6px]" : "min-w-0 flex-[2] mr-0"
+										}
+										onClick={() => handlePrimaryButtonClick(inputValue, selectedImages)}>
+										<span className="min-w-0 truncate">{primaryButtonText}</span>
+									</Button>
+								</StandardTooltip>
+							)}
+							{secondaryButtonText && (
+								<StandardTooltip
+									content={
+										secondaryButtonText === t("chat:startNewTask.title")
+											? t("chat:startNewTask.tooltip")
+											: secondaryButtonText === t("chat:reject.title")
+												? t("chat:reject.tooltip")
+												: secondaryButtonText === t("chat:terminate.title")
+													? t("chat:terminate.tooltip")
+													: secondaryButtonText === t("chat:killCommand.title")
+														? t("chat:killCommand.tooltip")
+														: secondaryButtonText
+									}>
+									<Button
+										variant="secondary"
+										disabled={!enableButtons}
+										className="min-w-0 flex-1 ml-[6px]"
+										onClick={() => handleSecondaryButtonClick(inputValue, selectedImages)}>
+										<span className="min-w-0 truncate">{secondaryButtonText}</span>
+									</Button>
+								</StandardTooltip>
 							)}
 						</div>
 					)}
diff --git a/webview-ui/src/components/chat/__tests__/ChatView.scroll-debug-repro.spec.tsx b/webview-ui/src/components/chat/__tests__/ChatView.scroll-debug-repro.spec.tsx
index bdbd202830..e5c0920026 100644
--- a/webview-ui/src/components/chat/__tests__/ChatView.scroll-debug-repro.spec.tsx
+++ b/webview-ui/src/components/chat/__tests__/ChatView.scroll-debug-repro.spec.tsx
@@ -502,6 +502,41 @@ describe("ChatView scroll behavior regression coverage", () => {
 		await expectChevronVisible()
 	})
 
+	it("keeps pending approval controls visible while browsing history", async () => {
+		const baseTs = Date.now() - 3_000
+		const initialMessages = buildMessagesWithCheckpoint(baseTs)
+		await hydrate(2, initialMessages)
+		await waitForCalls(2)
+		await waitForCallsSettled()
+
+		const scrollable = getScrollable()
+		await act(async () => {
+			fireEvent.wheel(scrollable, { deltaY: -120 })
+		})
+		await expectChevronVisible()
+
+		await act(async () => {
+			postState([
+				...initialMessages,
+				{
+					type: "ask",
+					ask: "tool",
+					ts: baseTs + 4,
+					text: JSON.stringify({ tool: "finishTask" }),
+				},
+			])
+		})
+		await flushEffects()
+
+		expect(document.querySelector(".codicon-chevron-down")).toBeTruthy()
+		expect(document.querySelector("button[aria-label='chat:scrollToLatestCheckpoint']")).toBeNull()
+		expect(
+			Array.from(document.querySelectorAll("button")).some(
+				(button) => button.textContent === "chat:completeSubtaskAndReturn",
+			),
+		).toBe(true)
+	})
+
 	it("hydration completion cannot override user escape hatch", async () => {
 		await hydrate(Number.POSITIVE_INFINITY)
 		await waitForCalls(1)