diff --git a/webview-ui/src/components/chat/ChatView.tsx b/webview-ui/src/components/chat/ChatView.tsx
index 9adf603ee4..2b7f3319a1 100644
--- a/webview-ui/src/components/chat/ChatView.tsx
+++ b/webview-ui/src/components/chat/ChatView.tsx
@@ -256,6 +256,7 @@ const ChatViewComponent: React.ForwardRefRenderFunction<ChatViewRef, ChatViewPro
 							setEnableButtons(true)
 							setPrimaryButtonText(t("chat:retry.title"))
 							setSecondaryButtonText(t("chat:startNewTask.title"))
+							// Don't clear input on error - preserve user's message
 							break
 						case "mistake_limit_reached":
 							playSound("progress_loop")
@@ -380,10 +381,22 @@ const ChatViewComponent: React.ForwardRefRenderFunction<ChatViewRef, ChatViewPro
 								setSelectedImages([])
 								setClineAsk(undefined)
 								setEnableButtons(false)
+							} else if (
+								// Clear input only when tool execution starts successfully
+								// This happens after the user approves and the API starts processing
+								secondLastMessage?.ask === "tool" &&
+								!lastMessage.partial
+							) {
+								// Tool execution started successfully, safe to clear input
+								setInputValue("")
+								setSelectedImages([])
 							}
 							break
 						case "api_req_finished":
 						case "error":
+							// If we get an error, don't clear the input
+							// The input should already be preserved from not clearing it in handlePrimaryButtonClick
+							break
 						case "text":
 						case "browser_action":
 						case "browser_action_result":
@@ -646,9 +659,8 @@ const ChatViewComponent: React.ForwardRefRenderFunction<ChatViewRef, ChatViewPro
 							text: trimmedInput,
 							images: images,
 						})
-						// Clear input state after sending
-						setInputValue("")
-						setSelectedImages([])
+						// Don't clear input here - let handleChatReset do it when the tool succeeds
+						// This preserves the input if the tool fails
 					} else {
 						vscode.postMessage({ type: "askResponse", askResponse: "yesButtonClicked" })
 					}
@@ -701,7 +713,8 @@ const ChatViewComponent: React.ForwardRefRenderFunction<ChatViewRef, ChatViewPro
 							text: trimmedInput,
 							images: images,
 						})
-						// Clear input state after sending
+						// For rejection, we can clear the input since the user explicitly rejected
+						// and the message won't be lost
 						setInputValue("")
 						setSelectedImages([])
 					} else {
diff --git a/webview-ui/src/components/chat/__tests__/ChatView.input-preservation.spec.tsx b/webview-ui/src/components/chat/__tests__/ChatView.input-preservation.spec.tsx
new file mode 100644
index 0000000000..e47bec0cf7
--- /dev/null
+++ b/webview-ui/src/components/chat/__tests__/ChatView.input-preservation.spec.tsx
@@ -0,0 +1,671 @@
+// pnpm --filter @roo-code/vscode-webview test src/components/chat/__tests__/ChatView.input-preservation.spec.tsx
+
+import React from "react"
+import { render, waitFor, act, fireEvent, screen } from "@/utils/test-utils"
+import { QueryClient, QueryClientProvider } from "@tanstack/react-query"
+
+import { ExtensionStateContextProvider } from "@src/context/ExtensionStateContext"
+import { vscode } from "@src/utils/vscode"
+
+import ChatView, { ChatViewProps } from "../ChatView"
+
+// Define minimal types needed for testing
+interface ClineMessage {
+	type: "say" | "ask"
+	say?: string
+	ask?: string
+	ts: number
+	text?: string
+	partial?: boolean
+}
+
+interface ExtensionState {
+	version: string
+	clineMessages: ClineMessage[]
+	taskHistory: any[]
+	shouldShowAnnouncement: boolean
+	allowedCommands: string[]
+	alwaysAllowExecute: boolean
+	[key: string]: any
+}
+
+// Mock vscode API
+vi.mock("@src/utils/vscode", () => ({
+	vscode: {
+		postMessage: vi.fn(),
+	},
+}))
+
+// Mock use-sound hook
+const mockPlayFunction = vi.fn()
+vi.mock("use-sound", () => ({
+	default: vi.fn().mockImplementation(() => {
+		return [mockPlayFunction]
+	}),
+}))
+
+// Mock components that use ESM dependencies
+vi.mock("../BrowserSessionRow", () => ({
+	default: function MockBrowserSessionRow({ messages }: { messages: ClineMessage[] }) {
+		return <div data-testid="browser-session">{JSON.stringify(messages)}</div>
+	},
+}))
+
+vi.mock("../ChatRow", () => ({
+	default: function MockChatRow({ message }: { message: ClineMessage }) {
+		return <div data-testid="chat-row">{JSON.stringify(message)}</div>
+	},
+}))
+
+vi.mock("../AutoApproveMenu", () => ({
+	default: () => null,
+}))
+
+vi.mock("../../common/VersionIndicator", () => ({
+	default: vi.fn(() => null),
+}))
+
+vi.mock("../Announcement", () => ({
+	default: function MockAnnouncement({ hideAnnouncement }: { hideAnnouncement: () => void }) {
+		// eslint-disable-next-line @typescript-eslint/no-require-imports
+		const React = require("react")
+		return React.createElement(
+			"div",
+			{ "data-testid": "announcement-modal" },
+			React.createElement("div", null, "What's New"),
+			React.createElement("button", { onClick: hideAnnouncement }, "Close"),
+		)
+	},
+}))
+
+vi.mock("@/components/common/DismissibleUpsell", () => ({
+	default: function MockDismissibleUpsell({ children }: { children: React.ReactNode }) {
+		return <div data-testid="dismissible-upsell">{children}</div>
+	},
+}))
+
+vi.mock("../QueuedMessages", () => ({
+	QueuedMessages: function MockQueuedMessages() {
+		return null
+	},
+}))
+
+vi.mock("@src/components/welcome/RooTips", () => ({
+	default: function MockRooTips() {
+		return <div data-testid="roo-tips">Tips content</div>
+	},
+}))
+
+vi.mock("@src/components/welcome/RooHero", () => ({
+	default: function MockRooHero() {
+		return <div data-testid="roo-hero">Hero content</div>
+	},
+}))
+
+vi.mock("../common/TelemetryBanner", () => ({
+	default: function MockTelemetryBanner() {
+		return null
+	},
+}))
+
+// Mock i18n
+vi.mock("react-i18next", () => ({
+	useTranslation: () => ({
+		t: (key: string) => {
+			const translations: Record<string, string> = {
+				"chat:save.title": "Save",
+				"chat:reject.title": "Reject",
+				"chat:approve.title": "Approve",
+				"chat:retry.title": "Retry",
+				"chat:startNewTask.title": "Start New Task",
+			}
+			return translations[key] || key
+		},
+	}),
+	initReactI18next: {
+		type: "3rdParty",
+		init: () => {},
+	},
+	Trans: ({ i18nKey, children }: { i18nKey: string; children?: React.ReactNode }) => {
+		return <>{children || i18nKey}</>
+	},
+}))
+
+// Mock ChatTextArea with controlled input
+vi.mock("../ChatTextArea", () => {
+	// eslint-disable-next-line @typescript-eslint/no-require-imports
+	const React = require("react")
+
+	const ChatTextAreaComponent = React.forwardRef(function MockChatTextArea(
+		props: {
+			onSend: () => void
+			inputValue?: string
+			setInputValue?: (value: string) => void
+			sendingDisabled?: boolean
+			placeholderText?: string
+			selectedImages?: string[]
+			setSelectedImages?: (images: string[]) => void
+			shouldDisableImages?: boolean
+		},
+		ref: React.ForwardedRef<{ focus: () => void }>,
+	) {
+		React.useImperativeHandle(ref, () => ({
+			focus: vi.fn(),
+		}))
+
+		return React.createElement(
+			"div",
+			{ "data-testid": "chat-textarea" },
+			React.createElement("input", {
+				type: "text",
+				value: props.inputValue || "",
+				onChange: (e: any) => props.setInputValue?.(e.target.value),
+				onKeyDown: (e: any) => {
+					if (e.key === "Enter" && !e.shiftKey) {
+						e.preventDefault()
+						props.onSend()
+					}
+				},
+				"data-sending-disabled": props.sendingDisabled,
+				placeholder: props.placeholderText,
+			}),
+		)
+	})
+
+	return {
+		default: ChatTextAreaComponent,
+		ChatTextArea: ChatTextAreaComponent,
+	}
+})
+
+// Mock VSCode components
+vi.mock("@vscode/webview-ui-toolkit/react", () => ({
+	VSCodeButton: function MockVSCodeButton({
+		children,
+		onClick,
+	}: {
+		children: React.ReactNode
+		onClick?: () => void
+	}) {
+		return <button onClick={onClick}>{children}</button>
+	},
+	VSCodeLink: function MockVSCodeLink({ children, href }: { children: React.ReactNode; href?: string }) {
+		return <a href={href}>{children}</a>
+	},
+}))
+
+// Mock UI components
+vi.mock("@src/components/ui", () => ({
+	StandardTooltip: ({ children }: { children: React.ReactNode }) => <>{children}</>,
+	Button: function MockButton({
+		children,
+		onClick,
+		disabled,
+		variant,
+		className,
+	}: {
+		children: React.ReactNode
+		onClick?: () => void
+		disabled?: boolean
+		variant?: string
+		className?: string
+	}) {
+		return (
+			<button
+				onClick={onClick}
+				disabled={disabled}
+				data-variant={variant}
+				className={className}
+				data-testid={
+					variant === "primary" ? "primary-button" : variant === "secondary" ? "secondary-button" : "button"
+				}>
+				{children}
+			</button>
+		)
+	},
+	Dialog: ({ children }: { children: React.ReactNode }) => <>{children}</>,
+	DialogContent: ({ children }: { children: React.ReactNode }) => <div>{children}</div>,
+	DialogHeader: ({ children }: { children: React.ReactNode }) => <div>{children}</div>,
+	DialogTitle: ({ children }: { children: React.ReactNode }) => <h2>{children}</h2>,
+	DialogDescription: ({ children }: { children: React.ReactNode }) => <p>{children}</p>,
+}))
+
+// Mock CloudUpsellDialog
+vi.mock("@src/components/cloud/CloudUpsellDialog", () => ({
+	CloudUpsellDialog: () => null,
+}))
+
+// Mock useCloudUpsell hook
+vi.mock("@src/hooks/useCloudUpsell", () => ({
+	useCloudUpsell: () => ({
+		isOpen: false,
+		openUpsell: vi.fn(),
+		closeUpsell: vi.fn(),
+		handleConnect: vi.fn(),
+	}),
+}))
+
+const mockPostMessage = (state: Partial<ExtensionState>) => {
+	window.postMessage(
+		{
+			type: "state",
+			state: {
+				version: "1.0.0",
+				clineMessages: [],
+				taskHistory: [],
+				shouldShowAnnouncement: false,
+				allowedCommands: [],
+				alwaysAllowExecute: false,
+				cloudIsAuthenticated: false,
+				telemetrySetting: "enabled",
+				...state,
+			},
+		},
+		"*",
+	)
+}
+
+const defaultProps: ChatViewProps = {
+	isHidden: false,
+	showAnnouncement: false,
+	hideAnnouncement: () => {},
+}
+
+const queryClient = new QueryClient()
+
+const renderChatView = (props: Partial<ChatViewProps> = {}) => {
+	return render(
+		<ExtensionStateContextProvider>
+			<QueryClientProvider client={queryClient}>
+				<ChatView {...defaultProps} {...props} />
+			</QueryClientProvider>
+		</ExtensionStateContextProvider>,
+	)
+}
+
+describe("ChatView - Input Preservation on Tool Errors", () => {
+	beforeEach(() => {
+		vi.clearAllMocks()
+	})
+
+	it("preserves user input when tool execution fails after approval", async () => {
+		renderChatView()
+
+		// Set up initial state with a tool ask
+		mockPostMessage({
+			clineMessages: [
+				{
+					type: "say",
+					say: "task",
+					ts: Date.now() - 2000,
+					text: "Initial task",
+				},
+				{
+					type: "ask",
+					ask: "tool",
+					ts: Date.now(),
+					text: JSON.stringify({
+						tool: "editedExistingFile",
+						path: "test.txt",
+						content: "new content",
+					}),
+					partial: false,
+				},
+			],
+		})
+
+		// Wait for buttons to appear
+		await waitFor(() => {
+			expect(screen.getByTestId("primary-button")).toBeInTheDocument()
+			expect(screen.getByTestId("primary-button")).toHaveTextContent("Save")
+		})
+
+		// Type a message in the input
+		const input = screen.getByTestId("chat-textarea").querySelector("input")!
+		await act(async () => {
+			fireEvent.change(input, { target: { value: "Please fix the indentation" } })
+		})
+
+		// Verify input has the value
+		expect(input.value).toBe("Please fix the indentation")
+
+		// Clear mock to track only the approval message
+		vi.mocked(vscode.postMessage).mockClear()
+
+		// Click Save button
+		const saveButton = screen.getByTestId("primary-button")
+		await act(async () => {
+			fireEvent.click(saveButton)
+		})
+
+		// Verify the message was sent with the user's text
+		expect(vscode.postMessage).toHaveBeenCalledWith({
+			type: "askResponse",
+			askResponse: "yesButtonClicked",
+			text: "Please fix the indentation",
+			images: [],
+		})
+
+		// Simulate an error occurring during tool execution
+		mockPostMessage({
+			clineMessages: [
+				{
+					type: "say",
+					say: "task",
+					ts: Date.now() - 3000,
+					text: "Initial task",
+				},
+				{
+					type: "ask",
+					ask: "tool",
+					ts: Date.now() - 2000,
+					text: JSON.stringify({
+						tool: "editedExistingFile",
+						path: "test.txt",
+						content: "new content",
+					}),
+					partial: false,
+				},
+				{
+					type: "say",
+					say: "error",
+					ts: Date.now() - 1000,
+					text: "Failed to apply diff: merge conflict",
+				},
+				{
+					type: "ask",
+					ask: "api_req_failed",
+					ts: Date.now(),
+					text: "The operation failed. Would you like to retry?",
+					partial: false,
+				},
+			],
+		})
+
+		// Wait for error state
+		await waitFor(() => {
+			expect(screen.getByTestId("primary-button")).toHaveTextContent("Retry")
+		})
+
+		// IMPORTANT: Verify that the user's input is still preserved
+		expect(input.value).toBe("Please fix the indentation")
+	})
+
+	it("clears input when user explicitly rejects the tool", async () => {
+		renderChatView()
+
+		// Set up initial state with a tool ask
+		mockPostMessage({
+			clineMessages: [
+				{
+					type: "say",
+					say: "task",
+					ts: Date.now() - 2000,
+					text: "Initial task",
+				},
+				{
+					type: "ask",
+					ask: "tool",
+					ts: Date.now(),
+					text: JSON.stringify({
+						tool: "editedExistingFile",
+						path: "test.txt",
+						content: "new content",
+					}),
+					partial: false,
+				},
+			],
+		})
+
+		// Wait for buttons to appear
+		await waitFor(() => {
+			expect(screen.getByTestId("secondary-button")).toBeInTheDocument()
+			expect(screen.getByTestId("secondary-button")).toHaveTextContent("Reject")
+		})
+
+		// Type a message in the input
+		const input = screen.getByTestId("chat-textarea").querySelector("input")!
+		await act(async () => {
+			fireEvent.change(input, { target: { value: "Don't make this change" } })
+		})
+
+		// Verify input has the value
+		expect(input.value).toBe("Don't make this change")
+
+		// Clear mock to track only the rejection message
+		vi.mocked(vscode.postMessage).mockClear()
+
+		// Click Reject button
+		const rejectButton = screen.getByTestId("secondary-button")
+		await act(async () => {
+			fireEvent.click(rejectButton)
+		})
+
+		// Verify the message was sent with the user's text
+		expect(vscode.postMessage).toHaveBeenCalledWith({
+			type: "askResponse",
+			askResponse: "noButtonClicked",
+			text: "Don't make this change",
+			images: [],
+		})
+
+		// For rejection, input should be cleared since user explicitly rejected
+		expect(input.value).toBe("")
+	})
+
+	it("clears input only after successful tool execution", async () => {
+		renderChatView()
+
+		// Set up initial state with a tool ask
+		mockPostMessage({
+			clineMessages: [
+				{
+					type: "say",
+					say: "task",
+					ts: Date.now() - 2000,
+					text: "Initial task",
+				},
+				{
+					type: "ask",
+					ask: "tool",
+					ts: Date.now(),
+					text: JSON.stringify({
+						tool: "editedExistingFile",
+						path: "test.txt",
+						content: "new content",
+					}),
+					partial: false,
+				},
+			],
+		})
+
+		// Wait for buttons to appear
+		await waitFor(() => {
+			expect(screen.getByTestId("primary-button")).toBeInTheDocument()
+		})
+
+		// Type a message in the input
+		const input = screen.getByTestId("chat-textarea").querySelector("input")!
+		await act(async () => {
+			fireEvent.change(input, { target: { value: "Looks good, please proceed" } })
+		})
+
+		// Click Save button
+		const saveButton = screen.getByTestId("primary-button")
+		await act(async () => {
+			fireEvent.click(saveButton)
+		})
+
+		// Input should still be there initially
+		expect(input.value).toBe("Looks good, please proceed")
+
+		// Simulate successful tool execution (api_req_started after tool approval)
+		mockPostMessage({
+			clineMessages: [
+				{
+					type: "say",
+					say: "task",
+					ts: Date.now() - 3000,
+					text: "Initial task",
+				},
+				{
+					type: "ask",
+					ask: "tool",
+					ts: Date.now() - 2000,
+					text: JSON.stringify({
+						tool: "editedExistingFile",
+						path: "test.txt",
+						content: "new content",
+					}),
+					partial: false,
+				},
+				{
+					type: "say",
+					say: "api_req_started",
+					ts: Date.now(),
+					text: JSON.stringify({ apiProtocol: "anthropic" }),
+					partial: false,
+				},
+			],
+		})
+
+		// Wait for state update
+		await waitFor(() => {
+			// After successful tool execution start, input should be cleared
+			expect(input.value).toBe("")
+		})
+	})
+
+	it("preserves input when multiple errors occur in sequence", async () => {
+		renderChatView()
+
+		// Set up initial state with a tool ask
+		mockPostMessage({
+			clineMessages: [
+				{
+					type: "say",
+					say: "task",
+					ts: Date.now() - 2000,
+					text: "Initial task",
+				},
+				{
+					type: "ask",
+					ask: "tool",
+					ts: Date.now(),
+					text: JSON.stringify({
+						tool: "editedExistingFile",
+						path: "test.txt",
+						content: "new content",
+					}),
+					partial: false,
+				},
+			],
+		})
+
+		// Type a message
+		const input = screen.getByTestId("chat-textarea").querySelector("input")!
+		await act(async () => {
+			fireEvent.change(input, { target: { value: "Important context for the fix" } })
+		})
+
+		// Click Save
+		const saveButton = screen.getByTestId("primary-button")
+		await act(async () => {
+			fireEvent.click(saveButton)
+		})
+
+		// First error
+		mockPostMessage({
+			clineMessages: [
+				{
+					type: "say",
+					say: "task",
+					ts: Date.now() - 4000,
+					text: "Initial task",
+				},
+				{
+					type: "ask",
+					ask: "tool",
+					ts: Date.now() - 3000,
+					text: JSON.stringify({
+						tool: "editedExistingFile",
+						path: "test.txt",
+						content: "new content",
+					}),
+					partial: false,
+				},
+				{
+					type: "say",
+					say: "error",
+					ts: Date.now() - 2000,
+					text: "First error: File not found",
+				},
+				{
+					type: "ask",
+					ask: "api_req_failed",
+					ts: Date.now() - 1000,
+					text: "The operation failed. Would you like to retry?",
+					partial: false,
+				},
+			],
+		})
+
+		// Input should still be preserved after first error
+		await waitFor(() => {
+			expect(input.value).toBe("Important context for the fix")
+		})
+
+		// Click Retry
+		await act(async () => {
+			const retryButton = screen.getByTestId("primary-button")
+			fireEvent.click(retryButton)
+		})
+
+		// Second error
+		mockPostMessage({
+			clineMessages: [
+				{
+					type: "say",
+					say: "task",
+					ts: Date.now() - 5000,
+					text: "Initial task",
+				},
+				{
+					type: "ask",
+					ask: "tool",
+					ts: Date.now() - 4000,
+					text: JSON.stringify({
+						tool: "editedExistingFile",
+						path: "test.txt",
+						content: "new content",
+					}),
+					partial: false,
+				},
+				{
+					type: "say",
+					say: "error",
+					ts: Date.now() - 3000,
+					text: "First error: File not found",
+				},
+				{
+					type: "say",
+					say: "error",
+					ts: Date.now() - 2000,
+					text: "Second error: Permission denied",
+				},
+				{
+					type: "ask",
+					ask: "api_req_failed",
+					ts: Date.now(),
+					text: "The operation failed again. Would you like to retry?",
+					partial: false,
+				},
+			],
+		})
+
+		// Input should STILL be preserved after second error
+		await waitFor(() => {
+			expect(input.value).toBe("Important context for the fix")
+		})
+	})
+})