diff --git a/webview-ui/src/components/chat/ChatView.tsx b/webview-ui/src/components/chat/ChatView.tsx
index b6c3b0bdf0..988c98ba30 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 (
@@ -1735,7 +1736,7 @@ 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 && !hasApprovalButtons ? (
 								<>
 									<StandardTooltip content={t("chat:scrollToBottom")}>
 										<Button
@@ -1759,6 +1760,16 @@ const ChatViewComponent: React.ForwardRefRenderFunction<ChatViewRef, ChatViewPro
 								</>
 							) : (
 								<>
+									{showScrollToBottom && (
+										<StandardTooltip content={t("chat:scrollToBottom")}>
+											<Button
+												variant="secondary"
+												className="w-9 shrink-0 mr-[6px]"
+												onClick={handleScrollToBottomAndResetCheckpointCursor}>
+												<span className="codicon codicon-chevron-down"></span>
+											</Button>
+										</StandardTooltip>
+									)}
 									{primaryButtonText && (
 										<StandardTooltip
 											content={
@@ -1780,14 +1791,18 @@ const ChatViewComponent: React.ForwardRefRenderFunction<ChatViewRef, ChatViewPro
 																			: primaryButtonText ===
 																				  t("chat:proceedWhileRunning.title")
 																				? t("chat:proceedWhileRunning.tooltip")
-																				: undefined
+																				: primaryButtonText
 											}>
 											<Button
 												variant="primary"
 												disabled={!enableButtons}
-												className={secondaryButtonText ? "flex-1 mr-[6px]" : "flex-[2] mr-0"}
+												className={
+													secondaryButtonText
+														? "min-w-0 flex-1 mr-[6px]"
+														: "min-w-0 flex-[2] mr-0"
+												}
 												onClick={() => handlePrimaryButtonClick(inputValue, selectedImages)}>
-												{primaryButtonText}
+												<span className="min-w-0 truncate">{primaryButtonText}</span>
 											</Button>
 										</StandardTooltip>
 									)}
@@ -1802,14 +1817,14 @@ const ChatViewComponent: React.ForwardRefRenderFunction<ChatViewRef, ChatViewPro
 															? t("chat:terminate.tooltip")
 															: secondaryButtonText === t("chat:killCommand.title")
 																? t("chat:killCommand.tooltip")
-																: undefined
+																: secondaryButtonText
 											}>
 											<Button
 												variant="secondary"
 												disabled={!enableButtons}
-												className="flex-1 ml-[6px]"
+												className="min-w-0 flex-1 ml-[6px]"
 												onClick={() => handleSecondaryButtonClick(inputValue, selectedImages)}>
-												{secondaryButtonText}
+												<span className="min-w-0 truncate">{secondaryButtonText}</span>
 											</Button>
 										</StandardTooltip>
 									)}
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..56b008b862 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
@@ -3,6 +3,8 @@ import { act, fireEvent, renderWithExtensionState } from "@/utils/test-utils"
 
 import type { ClineMessage } from "@roo-code/types"
 
+import { vscode } from "@src/utils/vscode"
+
 import ChatView, { type ChatViewProps } from "../ChatView"
 
 type FollowOutput = ((isAtBottom: boolean) => "auto" | false) | "auto" | false
@@ -98,7 +100,9 @@ vi.mock("@/components/ui", async (importOriginal) => {
 	const actual = await importOriginal<typeof import("@/components/ui")>()
 	return {
 		...actual,
-		StandardTooltip: ({ children }: { children: React.ReactNode }) => <>{children}</>,
+		StandardTooltip: ({ children, content }: { children: React.ReactNode; content?: string }) => (
+			<div data-tooltip={content}>{children}</div>
+		),
 	}
 })
 
@@ -357,9 +361,18 @@ const getScrollToCheckpointButton = (): HTMLButtonElement => {
 	return button
 }
 
+const getButtonByText = (text: string): HTMLButtonElement => {
+	const button = Array.from(document.querySelectorAll("button")).find((candidate) => candidate.textContent === text)
+	if (!(button instanceof HTMLButtonElement)) {
+		throw new Error(`Expected button with text: ${text}`)
+	}
+	return button
+}
+
 describe("ChatView scroll behavior regression coverage", () => {
 	beforeEach(() => {
 		vi.useFakeTimers()
+		vi.mocked(vscode.postMessage).mockClear()
 		harness.scrollCalls = 0
 		harness.scrollToIndexArgs = []
 		harness.atBottomAfterCalls = Number.POSITIVE_INFINITY
@@ -502,6 +515,78 @@ 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()
+		const completeButton = getButtonByText("chat:completeSubtaskAndReturn")
+		expect(completeButton.disabled).toBe(false)
+		expect(completeButton.closest("[data-tooltip]")?.getAttribute("data-tooltip")).toBe(
+			"chat:completeSubtaskAndReturn",
+		)
+
+		fireEvent.click(completeButton)
+		expect(vscode.postMessage).toHaveBeenCalledWith({ type: "askResponse", askResponse: "yesButtonClicked" })
+	})
+
+	it("keeps two-button approvals actionable while browsing history", async () => {
+		const baseTs = Date.now() - 3_000
+		await hydrate(2, buildMessages(baseTs))
+		await waitForCalls(2)
+		await waitForCallsSettled()
+
+		await act(async () => {
+			fireEvent.wheel(getScrollable(), { deltaY: -120 })
+			postState([
+				...buildMessages(baseTs),
+				{
+					type: "ask",
+					ask: "tool",
+					ts: baseTs + 3,
+					text: JSON.stringify({ tool: "editedExistingFile", batchDiffs: [] }),
+				},
+			])
+		})
+		await flushEffects()
+
+		expect(document.querySelector(".codicon-chevron-down")).toBeTruthy()
+		const approveButton = getButtonByText("chat:edit-batch.approve.title")
+		const denyButton = getButtonByText("chat:edit-batch.deny.title")
+		expect(approveButton.disabled).toBe(false)
+		expect(denyButton.disabled).toBe(false)
+		expect(approveButton.closest("[data-tooltip]")?.getAttribute("data-tooltip")).toBe(
+			"chat:edit-batch.approve.title",
+		)
+		expect(denyButton.closest("[data-tooltip]")?.getAttribute("data-tooltip")).toBe("chat:edit-batch.deny.title")
+
+		fireEvent.click(denyButton)
+		expect(vscode.postMessage).toHaveBeenCalledWith({ type: "askResponse", askResponse: "noButtonClicked" })
+	})
+
 	it("hydration completion cannot override user escape hatch", async () => {
 		await hydrate(Number.POSITIVE_INFINITY)
 		await waitForCalls(1)