diff --git a/src/core/webview/ClineProvider.ts b/src/core/webview/ClineProvider.ts
index 1fb272604d3..754c88d9081 100644
--- a/src/core/webview/ClineProvider.ts
+++ b/src/core/webview/ClineProvider.ts
@@ -145,6 +145,7 @@ export class ClineProvider
 	private recentTasksCache?: string[]
 	private pendingOperations: Map<string, PendingEditOperation> = new Map()
 	private static readonly PENDING_OPERATION_TIMEOUT_MS = 30000 // 30 seconds
+	private static readonly DRAFT_MESSAGE_KEY = "roo.draftMessage"
 
 	private cloudOrganizationsCache: CloudOrganizationMembership[] | null = null
 	private cloudOrganizationsCacheTimestamp: number | null = null
@@ -550,6 +551,43 @@ export class ClineProvider
 		this.log(`[clearAllPendingEditOperations] Cleared all pending operations`)
 	}
 
+	// Draft Message Management
+
+	/**
+	 * Save draft message to workspace state
+	 * @param text - The draft message text
+	 * @param images - Array of base64 image data URLs
+	 */
+	public async saveDraftMessage(text: string, images: string[]): Promise<void> {
+		// Don't save empty drafts
+		if (!text.trim() && images.length === 0) {
+			await this.clearDraftMessage()
+			return
+		}
+
+		const draft = {
+			text,
+			images,
+			timestamp: Date.now(),
+		}
+		await this.context.workspaceState.update(ClineProvider.DRAFT_MESSAGE_KEY, draft)
+	}
+
+	/**
+	 * Get draft message from workspace state
+	 * @returns The saved draft or undefined
+	 */
+	public getDraftMessage(): { text: string; images: string[]; timestamp: number } | undefined {
+		return this.context.workspaceState.get(ClineProvider.DRAFT_MESSAGE_KEY)
+	}
+
+	/**
+	 * Clear draft message from workspace state
+	 */
+	public async clearDraftMessage(): Promise<void> {
+		await this.context.workspaceState.update(ClineProvider.DRAFT_MESSAGE_KEY, undefined)
+	}
+
 	/*
 	VSCode extensions use the disposable pattern to clean up resources when the sidebar/editor tab is closed by the user or system. This applies to event listening, commands, interacting with the UI, etc.
 	- https://vscode-docs.readthedocs.io/en/stable/extensions/patterns-and-principles/
diff --git a/src/core/webview/__tests__/webviewMessageHandler.draftMessage.spec.ts b/src/core/webview/__tests__/webviewMessageHandler.draftMessage.spec.ts
new file mode 100644
index 00000000000..bd1c8b61680
--- /dev/null
+++ b/src/core/webview/__tests__/webviewMessageHandler.draftMessage.spec.ts
@@ -0,0 +1,150 @@
+// npx vitest run src/core/webview/__tests__/webviewMessageHandler.draftMessage.spec.ts
+
+import { webviewMessageHandler } from "../webviewMessageHandler"
+import type { ClineProvider } from "../ClineProvider"
+
+vi.mock("vscode", () => ({
+	window: {
+		showInformationMessage: vi.fn(),
+		showErrorMessage: vi.fn(),
+	},
+	workspace: {
+		workspaceFolders: [{ uri: { fsPath: "/mock/workspace" } }],
+	},
+}))
+
+describe("webviewMessageHandler - Draft Message", () => {
+	let mockClineProvider: ClineProvider
+
+	beforeEach(() => {
+		vi.clearAllMocks()
+
+		mockClineProvider = {
+			saveDraftMessage: vi.fn().mockResolvedValue(undefined),
+			getDraftMessage: vi.fn(),
+			clearDraftMessage: vi.fn().mockResolvedValue(undefined),
+			postMessageToWebview: vi.fn(),
+			getState: vi.fn().mockResolvedValue({
+				apiConfiguration: {},
+			}),
+			contextProxy: {
+				context: {
+					extensionPath: "/mock/extension/path",
+					globalStorageUri: { fsPath: "/mock/global/storage" },
+				},
+				setValue: vi.fn(),
+				getValue: vi.fn(),
+			},
+			log: vi.fn(),
+		} as unknown as ClineProvider
+	})
+
+	describe("saveDraftMessage", () => {
+		it("should save draft message with text and images", async () => {
+			await webviewMessageHandler(mockClineProvider, {
+				type: "saveDraftMessage",
+				text: "Test draft message",
+				images: ["data:image/png;base64,abc123"],
+			})
+
+			expect(mockClineProvider.saveDraftMessage).toHaveBeenCalledWith("Test draft message", [
+				"data:image/png;base64,abc123",
+			])
+		})
+
+		it("should save draft message with only text", async () => {
+			await webviewMessageHandler(mockClineProvider, {
+				type: "saveDraftMessage",
+				text: "Text only draft",
+			})
+
+			expect(mockClineProvider.saveDraftMessage).toHaveBeenCalledWith("Text only draft", [])
+		})
+
+		it("should save draft message with only images", async () => {
+			await webviewMessageHandler(mockClineProvider, {
+				type: "saveDraftMessage",
+				images: ["data:image/png;base64,image1", "data:image/png;base64,image2"],
+			})
+
+			expect(mockClineProvider.saveDraftMessage).toHaveBeenCalledWith("", [
+				"data:image/png;base64,image1",
+				"data:image/png;base64,image2",
+			])
+		})
+
+		it("should handle empty text and images", async () => {
+			await webviewMessageHandler(mockClineProvider, {
+				type: "saveDraftMessage",
+			})
+
+			expect(mockClineProvider.saveDraftMessage).toHaveBeenCalledWith("", [])
+		})
+	})
+
+	describe("getDraftMessage", () => {
+		it("should return saved draft with text and images", async () => {
+			const mockDraft = {
+				text: "Saved draft",
+				images: ["data:image/png;base64,savedImage"],
+				timestamp: 1234567890,
+			}
+			;(mockClineProvider.getDraftMessage as ReturnType<typeof vi.fn>).mockReturnValue(mockDraft)
+
+			await webviewMessageHandler(mockClineProvider, {
+				type: "getDraftMessage",
+			})
+
+			expect(mockClineProvider.getDraftMessage).toHaveBeenCalled()
+			expect(mockClineProvider.postMessageToWebview).toHaveBeenCalledWith({
+				type: "draftMessage",
+				text: "Saved draft",
+				images: ["data:image/png;base64,savedImage"],
+			})
+		})
+
+		it("should handle when no draft is saved", async () => {
+			;(mockClineProvider.getDraftMessage as ReturnType<typeof vi.fn>).mockReturnValue(undefined)
+
+			await webviewMessageHandler(mockClineProvider, {
+				type: "getDraftMessage",
+			})
+
+			expect(mockClineProvider.getDraftMessage).toHaveBeenCalled()
+			expect(mockClineProvider.postMessageToWebview).toHaveBeenCalledWith({
+				type: "draftMessage",
+				text: undefined,
+				images: undefined,
+			})
+		})
+
+		it("should handle draft with only text", async () => {
+			const mockDraft = {
+				text: "Text only",
+				images: [],
+				timestamp: 1234567890,
+			}
+			;(mockClineProvider.getDraftMessage as ReturnType<typeof vi.fn>).mockReturnValue(mockDraft)
+
+			await webviewMessageHandler(mockClineProvider, {
+				type: "getDraftMessage",
+			})
+
+			expect(mockClineProvider.postMessageToWebview).toHaveBeenCalledWith({
+				type: "draftMessage",
+				text: "Text only",
+				images: [],
+			})
+		})
+	})
+
+	describe("clearDraftMessage", () => {
+		it("should clear the draft message", async () => {
+			await webviewMessageHandler(mockClineProvider, {
+				type: "clearDraftMessage",
+			})
+
+			expect(mockClineProvider.clearDraftMessage).toHaveBeenCalled()
+		})
+	})
+})
diff --git a/src/core/webview/webviewMessageHandler.ts b/src/core/webview/webviewMessageHandler.ts
index 21a515b6107..c9a1ea957d5 100644
--- a/src/core/webview/webviewMessageHandler.ts
+++ b/src/core/webview/webviewMessageHandler.ts
@@ -3100,6 +3100,28 @@ export const webviewMessageHandler = async (
 			break
 		}
 
+		/**
+		 * Draft Message Persistence
+		 */
+
+		case "saveDraftMessage":
+			await provider.saveDraftMessage(message.text || "", message.images || [])
+			break
+
+		case "getDraftMessage": {
+			const draft = provider.getDraftMessage()
+			await provider.postMessageToWebview({
+				type: "draftMessage",
+				text: draft?.text,
+				images: draft?.images,
+			})
+			break
+		}
+
+		case "clearDraftMessage":
+			await provider.clearDraftMessage()
+			break
+
 		default: {
 			// console.log(`Unhandled message type: ${message.type}`)
 			//
diff --git a/src/shared/ExtensionMessage.ts b/src/shared/ExtensionMessage.ts
index b9424f0bf21..47da08b2726 100644
--- a/src/shared/ExtensionMessage.ts
+++ b/src/shared/ExtensionMessage.ts
@@ -131,6 +131,7 @@ export interface ExtensionMessage {
 		| "interactionRequired"
 		| "browserSessionUpdate"
 		| "browserSessionNavigate"
+		| "draftMessage"
 	text?: string
 	payload?: any // Add a generic payload for now, can refine later
 	// Checkpoint warning message
diff --git a/src/shared/WebviewMessage.ts b/src/shared/WebviewMessage.ts
index eeae8e70cb0..fcf0de63d87 100644
--- a/src/shared/WebviewMessage.ts
+++ b/src/shared/WebviewMessage.ts
@@ -175,6 +175,9 @@ export interface WebviewMessage {
 		| "browserPanelDidLaunch"
 		| "openDebugApiHistory"
 		| "openDebugUiHistory"
+		| "saveDraftMessage"
+		| "getDraftMessage"
+		| "clearDraftMessage"
 	text?: string
 	editedMessageContent?: string
 	tab?: "settings" | "history" | "mcp" | "modes" | "chat" | "marketplace" | "cloud"
diff --git a/webview-ui/src/components/chat/ChatView.tsx b/webview-ui/src/components/chat/ChatView.tsx
index 243e583613b..53102d9b1d8 100644
--- a/webview-ui/src/components/chat/ChatView.tsx
+++ b/webview-ui/src/components/chat/ChatView.tsx
@@ -137,6 +137,29 @@ const ChatViewComponent: React.ForwardRefRenderFunction<ChatViewRef, ChatViewPro
 	const [sendingDisabled, setSendingDisabled] = useState(false)
 	const [selectedImages, setSelectedImages] = useState<string[]>([])
 
+	// Debounced draft save to prevent excessive writes
+	const saveDraftDebounced = useMemo(
+		() =>
+			debounce((text: string, images: string[]) => {
+				vscode.postMessage({ type: "saveDraftMessage", text, images })
+			}, 500),
+		[],
+	)
+
+	// Cleanup debounce on unmount
+	useEffect(() => {
+		return () => {
+			if (saveDraftDebounced && typeof (saveDraftDebounced as any).clear === "function") {
+				;(saveDraftDebounced as any).clear()
+			}
+		}
+	}, [saveDraftDebounced])
+
+	// Request saved draft on mount
+	useEffect(() => {
+		vscode.postMessage({ type: "getDraftMessage" })
+	}, [])
+
 	// We need to hold on to the ask because useEffect > lastMessage will always
 	// let us know when an ask comes in and handle it, but by the time
 	// handleMessage is called, the last message might not be the ask anymore
@@ -557,8 +580,20 @@ const ChatViewComponent: React.ForwardRefRenderFunction<ChatViewRef, ChatViewPro
 		// setPrimaryButtonText(undefined)
 		// setSecondaryButtonText(undefined)
 		disableAutoScrollRef.current = false
+
+		// Clear saved draft
+		vscode.postMessage({ type: "clearDraftMessage" })
 	}, [])
 
+	// Wrapper to save draft when input value changes
+	const handleInputValueChange = useCallback(
+		(value: string) => {
+			setInputValue(value)
+			saveDraftDebounced(value, selectedImages)
+		},
+		[selectedImages, saveDraftDebounced],
+	)
+
 	/**
 	 * Handles sending messages to the extension
 	 * @param text - The message text to send
@@ -840,6 +875,17 @@ const ChatViewComponent: React.ForwardRefRenderFunction<ChatViewRef, ChatViewPro
 				case "interactionRequired":
 					playSound("notification")
 					break
+				case "draftMessage":
+					// Only restore draft if there's no active task input
+					if (messagesRef.current.length === 0 || clineAskRef.current === undefined) {
+						if (message.text) {
+							setInputValue(message.text)
+						}
+						if (message.images && message.images.length > 0) {
+							setSelectedImages(message.images)
+						}
+					}
+					break
 			}
 			// textAreaRef.current is not explicitly required here since React
 			// guarantees that ref will be stable across re-renders, and we're
@@ -1568,7 +1614,7 @@ const ChatViewComponent: React.ForwardRefRenderFunction<ChatViewRef, ChatViewPro
 			<ChatTextArea
 				ref={textAreaRef}
 				inputValue={inputValue}
-				setInputValue={setInputValue}
+				setInputValue={handleInputValueChange}
 				sendingDisabled={sendingDisabled || isProfileDisabled}
 				selectApiConfigDisabled={sendingDisabled && clineAsk !== "api_req_failed"}
 				placeholderText={placeholderText}