diff --git a/apps/cli/src/__tests__/extension-host.test.ts b/apps/cli/src/__tests__/extension-host.test.ts
index 55f299d0e8..af46f945ff 100644
--- a/apps/cli/src/__tests__/extension-host.test.ts
+++ b/apps/cli/src/__tests__/extension-host.test.ts
@@ -1,8 +1,13 @@
 // pnpm --filter @roo-code/cli test src/__tests__/extension-host.test.ts
 
-import { ExtensionHost, type ExtensionHostOptions } from "../extension-host.js"
 import { EventEmitter } from "events"
-import type { ProviderName } from "@roo-code/types"
+import fs from "fs"
+import os from "os"
+import path from "path"
+
+import type { ProviderName, WebviewMessage } from "@roo-code/types"
+
+import { ExtensionHost, type ExtensionHostOptions } from "../extension-host.js"
 
 vi.mock("@roo-code/vscode-shim", () => ({
 	createVSCodeAPI: vi.fn(() => ({
@@ -369,15 +374,15 @@ describe("ExtensionHost", () => {
 				const emitSpy = vi.spyOn(host, "emit")
 
 				// Queue messages before ready
-				host.sendToExtension({ type: "test1" })
-				host.sendToExtension({ type: "test2" })
+				host.sendToExtension({ type: "requestModes" })
+				host.sendToExtension({ type: "requestCommands" })
 
 				// Mark ready (should flush)
 				host.markWebviewReady()
 
 				// Check that webviewMessage events were emitted for pending messages
-				expect(emitSpy).toHaveBeenCalledWith("webviewMessage", { type: "test1" })
-				expect(emitSpy).toHaveBeenCalledWith("webviewMessage", { type: "test2" })
+				expect(emitSpy).toHaveBeenCalledWith("webviewMessage", { type: "requestModes" })
+				expect(emitSpy).toHaveBeenCalledWith("webviewMessage", { type: "requestCommands" })
 			})
 		})
 	})
@@ -385,7 +390,7 @@ describe("ExtensionHost", () => {
 	describe("sendToExtension", () => {
 		it("should queue message when webview not ready", () => {
 			const host = createTestHost()
-			const message = { type: "test" }
+			const message: WebviewMessage = { type: "requestModes" }
 
 			host.sendToExtension(message)
 
@@ -396,7 +401,7 @@ describe("ExtensionHost", () => {
 		it("should emit webviewMessage event when webview is ready", () => {
 			const host = createTestHost()
 			const emitSpy = vi.spyOn(host, "emit")
-			const message = { type: "test" }
+			const message: WebviewMessage = { type: "requestModes" }
 
 			host.markWebviewReady()
 			host.sendToExtension(message)
@@ -408,7 +413,7 @@ describe("ExtensionHost", () => {
 			const host = createTestHost()
 
 			host.markWebviewReady()
-			host.sendToExtension({ type: "test" })
+			host.sendToExtension({ type: "requestModes" })
 
 			const pending = getPrivate<unknown[]>(host, "pendingMessages")
 			expect(pending).toHaveLength(0)
@@ -792,7 +797,7 @@ describe("ExtensionHost", () => {
 			callPrivate(host, "handleFollowupQuestionWithTimeout", 123, text)
 
 			// Should show prompt with timeout hint
-			expect(stdoutWriteSpy).toHaveBeenCalledWith(expect.stringContaining("auto-select in 10s"))
+			expect(stdoutWriteSpy).toHaveBeenCalledWith(expect.stringContaining("auto-select in 60s"))
 		})
 	})
 
@@ -1144,9 +1149,8 @@ describe("ExtensionHost", () => {
 		})
 	})
 
-	describe("handleStateMessage - mode change detection", () => {
+	describe("handleStateMessage - mode tracking", () => {
 		let host: ExtensionHost
-		let sendToExtensionSpy: ReturnType<typeof vi.spyOn>
 
 		beforeEach(() => {
 			host = createTestHost({
@@ -1157,99 +1161,194 @@ describe("ExtensionHost", () => {
 			})
 			// Mock process.stdout.write which is used by output()
 			vi.spyOn(process.stdout, "write").mockImplementation(() => true)
-			sendToExtensionSpy = vi.spyOn(host, "sendToExtension")
 		})
 
 		afterEach(() => {
 			vi.restoreAllMocks()
 		})
 
-		it("should re-apply API configuration when mode changes in state", () => {
-			// First state update establishes current mode
+		it("should track current mode when state updates with a mode", () => {
+			// Initial state update establishes current mode
 			callPrivate(host, "handleStateMessage", { type: "state", state: { mode: "code", clineMessages: [] } })
-			sendToExtensionSpy.mockClear()
+			expect(getPrivate(host, "currentMode")).toBe("code")
 
-			// Second state update with different mode should trigger re-apply
+			// Second state update should update tracked mode
 			callPrivate(host, "handleStateMessage", { type: "state", state: { mode: "architect", clineMessages: [] } })
-
-			// Should have sent updateSettings with the API configuration
-			expect(sendToExtensionSpy).toHaveBeenCalledWith(
-				expect.objectContaining({
-					type: "updateSettings",
-					updatedSettings: expect.objectContaining({
-						apiProvider: "anthropic",
-						apiKey: "test-key",
-						apiModelId: "test-model",
-					}),
-				}),
-			)
+			expect(getPrivate(host, "currentMode")).toBe("architect")
 		})
 
-		it("should not re-apply API configuration when mode stays the same", () => {
-			// First state update establishes current mode
+		it("should not change current mode when state has no mode", () => {
+			// Initial state update establishes current mode
 			callPrivate(host, "handleStateMessage", { type: "state", state: { mode: "code", clineMessages: [] } })
-			sendToExtensionSpy.mockClear()
+			expect(getPrivate(host, "currentMode")).toBe("code")
 
-			// Second state update with same mode should not trigger re-apply
-			callPrivate(host, "handleStateMessage", { type: "state", state: { mode: "code", clineMessages: [] } })
-
-			// Should not have sent updateSettings
-			expect(sendToExtensionSpy).not.toHaveBeenCalled()
-		})
-
-		it("should re-apply API configuration without apiKey when mode changes", () => {
-			// Create host without apiKey - API configuration should still be sent
-			// to preserve provider/model settings across mode switches
-			const hostNoKey = createTestHost({
-				mode: "code",
-				apiProvider: "anthropic",
-				model: "test-model",
-			})
-			const sendSpy = vi.spyOn(hostNoKey, "sendToExtension")
-
-			// First state update establishes current mode
-			callPrivate(hostNoKey, "handleStateMessage", { type: "state", state: { mode: "code", clineMessages: [] } })
-			sendSpy.mockClear()
-
-			// Second state update with different mode
-			callPrivate(hostNoKey, "handleStateMessage", {
-				type: "state",
-				state: { mode: "architect", clineMessages: [] },
-			})
-
-			// Should have sent updateSettings with provider and model (but no apiKey)
-			expect(sendSpy).toHaveBeenCalledWith(
-				expect.objectContaining({
-					type: "updateSettings",
-					updatedSettings: expect.objectContaining({
-						apiProvider: "anthropic",
-						apiModelId: "test-model",
-					}),
-				}),
-			)
-			// Verify apiKey is NOT in the config
-			const call = sendSpy.mock.calls[0]?.[0] as { updatedSettings: { apiKey?: string } } | undefined
-			expect(call?.updatedSettings.apiKey).toBeUndefined()
+			// State without mode should not change tracked mode
+			callPrivate(host, "handleStateMessage", { type: "state", state: { clineMessages: [] } })
+			expect(getPrivate(host, "currentMode")).toBe("code")
 		})
 
 		it("should track current mode across multiple changes", () => {
 			// Start with code mode
 			callPrivate(host, "handleStateMessage", { type: "state", state: { mode: "code", clineMessages: [] } })
-			sendToExtensionSpy.mockClear()
+			expect(getPrivate(host, "currentMode")).toBe("code")
 
 			// Change to architect
 			callPrivate(host, "handleStateMessage", { type: "state", state: { mode: "architect", clineMessages: [] } })
-			expect(sendToExtensionSpy).toHaveBeenCalledTimes(1)
-			sendToExtensionSpy.mockClear()
+			expect(getPrivate(host, "currentMode")).toBe("architect")
 
 			// Change to debug
 			callPrivate(host, "handleStateMessage", { type: "state", state: { mode: "debug", clineMessages: [] } })
-			expect(sendToExtensionSpy).toHaveBeenCalledTimes(1)
+			expect(getPrivate(host, "currentMode")).toBe("debug")
+
+			// Another state update with debug
+			callPrivate(host, "handleStateMessage", { type: "state", state: { mode: "debug", clineMessages: [] } })
+			expect(getPrivate(host, "currentMode")).toBe("debug")
+		})
+
+		it("should not send updateSettings on mode change (CLI settings are applied once during runTask)", () => {
+			// This test ensures mode changes don't trigger automatic re-application of API settings.
+			// CLI settings are applied once during runTask() via updateSettings.
+			// Mode-specific provider profiles are handled by the extension's handleModeSwitch.
+			const sendToExtensionSpy = vi.spyOn(host, "sendToExtension")
+
+			// Initial state
+			callPrivate(host, "handleStateMessage", { type: "state", state: { mode: "code", clineMessages: [] } })
 			sendToExtensionSpy.mockClear()
 
-			// Stay on debug
-			callPrivate(host, "handleStateMessage", { type: "state", state: { mode: "debug", clineMessages: [] } })
+			// Mode change should NOT trigger sendToExtension
+			callPrivate(host, "handleStateMessage", { type: "state", state: { mode: "architect", clineMessages: [] } })
 			expect(sendToExtensionSpy).not.toHaveBeenCalled()
 		})
 	})
+
+	describe("ephemeral mode", () => {
+		describe("constructor", () => {
+			it("should store ephemeral option", () => {
+				const host = createTestHost({ ephemeral: true })
+				const options = getPrivate<ExtensionHostOptions>(host, "options")
+				expect(options.ephemeral).toBe(true)
+			})
+
+			it("should default ephemeral to undefined", () => {
+				const host = createTestHost()
+				const options = getPrivate<ExtensionHostOptions>(host, "options")
+				expect(options.ephemeral).toBeUndefined()
+			})
+
+			it("should initialize ephemeralStorageDir to null", () => {
+				const host = createTestHost({ ephemeral: true })
+				expect(getPrivate(host, "ephemeralStorageDir")).toBeNull()
+			})
+		})
+
+		describe("createEphemeralStorageDir", () => {
+			let createdDirs: string[] = []
+
+			afterEach(async () => {
+				// Clean up any directories created during tests
+				for (const dir of createdDirs) {
+					try {
+						await fs.promises.rm(dir, { recursive: true, force: true })
+					} catch {
+						// Ignore cleanup errors
+					}
+				}
+				createdDirs = []
+			})
+
+			it("should create a directory in the system temp folder", async () => {
+				const host = createTestHost({ ephemeral: true })
+				const tmpDir = await callPrivate<Promise<string>>(host, "createEphemeralStorageDir")
+				createdDirs.push(tmpDir)
+
+				expect(tmpDir).toContain(os.tmpdir())
+				expect(tmpDir).toContain("roo-cli-")
+				expect(fs.existsSync(tmpDir)).toBe(true)
+			})
+
+			it("should create a unique directory each time", async () => {
+				const host = createTestHost({ ephemeral: true })
+				const dir1 = await callPrivate<Promise<string>>(host, "createEphemeralStorageDir")
+				const dir2 = await callPrivate<Promise<string>>(host, "createEphemeralStorageDir")
+				createdDirs.push(dir1, dir2)
+
+				expect(dir1).not.toBe(dir2)
+				expect(fs.existsSync(dir1)).toBe(true)
+				expect(fs.existsSync(dir2)).toBe(true)
+			})
+
+			it("should include timestamp and random id in directory name", async () => {
+				const host = createTestHost({ ephemeral: true })
+				const tmpDir = await callPrivate<Promise<string>>(host, "createEphemeralStorageDir")
+				createdDirs.push(tmpDir)
+
+				const dirName = path.basename(tmpDir)
+				// Format: roo-cli-{timestamp}-{randomId}
+				expect(dirName).toMatch(/^roo-cli-\d+-[a-z0-9]+$/)
+			})
+		})
+
+		describe("dispose - ephemeral cleanup", () => {
+			it("should clean up ephemeral storage directory on dispose", async () => {
+				const host = createTestHost({ ephemeral: true })
+
+				// Create the ephemeral directory
+				const tmpDir = await callPrivate<Promise<string>>(host, "createEphemeralStorageDir")
+				;(host as unknown as Record<string, unknown>).ephemeralStorageDir = tmpDir
+
+				// Verify directory exists
+				expect(fs.existsSync(tmpDir)).toBe(true)
+
+				// Dispose the host
+				await host.dispose()
+
+				// Directory should be removed
+				expect(fs.existsSync(tmpDir)).toBe(false)
+				expect(getPrivate(host, "ephemeralStorageDir")).toBeNull()
+			})
+
+			it("should not fail dispose if ephemeral directory doesn't exist", async () => {
+				const host = createTestHost({ ephemeral: true })
+
+				// Set a non-existent directory
+				;(host as unknown as Record<string, unknown>).ephemeralStorageDir = "/non/existent/path/roo-cli-test"
+
+				// Dispose should not throw
+				await expect(host.dispose()).resolves.toBeUndefined()
+			})
+
+			it("should clean up ephemeral directory with contents", async () => {
+				const host = createTestHost({ ephemeral: true })
+
+				// Create the ephemeral directory with some content
+				const tmpDir = await callPrivate<Promise<string>>(host, "createEphemeralStorageDir")
+				;(host as unknown as Record<string, unknown>).ephemeralStorageDir = tmpDir
+
+				// Add some files and subdirectories
+				await fs.promises.writeFile(path.join(tmpDir, "test.txt"), "test content")
+				await fs.promises.mkdir(path.join(tmpDir, "subdir"))
+				await fs.promises.writeFile(path.join(tmpDir, "subdir", "nested.txt"), "nested content")
+
+				// Verify content exists
+				expect(fs.existsSync(path.join(tmpDir, "test.txt"))).toBe(true)
+				expect(fs.existsSync(path.join(tmpDir, "subdir", "nested.txt"))).toBe(true)
+
+				// Dispose the host
+				await host.dispose()
+
+				// Directory and all contents should be removed
+				expect(fs.existsSync(tmpDir)).toBe(false)
+			})
+
+			it("should not clean up anything if not in ephemeral mode", async () => {
+				const host = createTestHost({ ephemeral: false })
+
+				// ephemeralStorageDir should be null
+				expect(getPrivate(host, "ephemeralStorageDir")).toBeNull()
+
+				// Dispose should complete normally
+				await expect(host.dispose()).resolves.toBeUndefined()
+			})
+		})
+	})
 })
diff --git a/apps/cli/src/extension-host.ts b/apps/cli/src/extension-host.ts
index c93109892e..6f7ec6e01e 100644
--- a/apps/cli/src/extension-host.ts
+++ b/apps/cli/src/extension-host.ts
@@ -16,8 +16,15 @@ import fs from "fs"
 import os from "os"
 import readline from "readline"
 
-import { ProviderName, ReasoningEffortExtended, RooCodeSettings, ExtensionMessage } from "@roo-code/types"
+import {
+	ProviderName,
+	ReasoningEffortExtended,
+	RooCodeSettings,
+	ExtensionMessage,
+	WebviewMessage,
+} from "@roo-code/types"
 import { createVSCodeAPI, setRuntimeConfigValues } from "@roo-code/vscode-shim"
+import { debugLog } from "@roo-code/core/debug-log"
 
 // Get the CLI package root directory (for finding node_modules/@vscode/ripgrep)
 // When bundled, import.meta.url points to dist/index.js, so go up to package root
@@ -40,6 +47,11 @@ export interface ExtensionHostOptions {
 	 * Use this when running in TUI mode where Ink controls the terminal.
 	 */
 	disableOutput?: boolean
+	/**
+	 * When true, uses a temporary storage directory that is cleaned up on exit.
+	 * No state persists between runs - all configuration from CLI flags/environment.
+	 */
+	ephemeral?: boolean
 }
 
 interface ExtensionModule {
@@ -54,8 +66,6 @@ interface WebviewViewProvider {
 	resolveWebviewView?(webviewView: unknown, context: unknown, token: unknown): void | Promise<void>
 }
 
-const DEBUG_LOG_PATH = path.join(os.homedir(), ".roo", "cli-debug.log")
-
 export class ExtensionHost extends EventEmitter {
 	private vscode: ReturnType<typeof createVSCodeAPI> | null = null
 	private extensionModule: ExtensionModule | null = null
@@ -94,6 +104,9 @@ export class ExtensionHost extends EventEmitter {
 	// Track the current mode to detect mode changes
 	private currentMode: string | null = null
 
+	// Track ephemeral storage directory for cleanup
+	private ephemeralStorageDir: string | null = null
+
 	constructor(options: ExtensionHostOptions) {
 		super()
 		this.options = options
@@ -105,48 +118,7 @@ export class ExtensionHost extends EventEmitter {
 	 * This avoids console output which breaks the TUI.
 	 */
 	private log(message: string, data?: unknown): void {
-		try {
-			const logDir = path.dirname(DEBUG_LOG_PATH)
-
-			if (!fs.existsSync(logDir)) {
-				fs.mkdirSync(logDir, { recursive: true })
-			}
-
-			const timestamp = new Date().toISOString()
-
-			const entry = data
-				? `[${timestamp}] ${message}: ${JSON.stringify(data, null, 2)}\n`
-				: `[${timestamp}] ${message}\n`
-
-			fs.appendFileSync(DEBUG_LOG_PATH, entry)
-		} catch {
-			// NO-OP
-		}
-	}
-
-	/**
-	 * Get the shape (keys) of an object for logging
-	 */
-	private getMessageShape(msg: unknown): Record<string, string> {
-		if (!msg || typeof msg !== "object") {
-			return { _type: typeof msg }
-		}
-
-		const shape: Record<string, string> = {}
-
-		for (const [key, value] of Object.entries(msg as Record<string, unknown>)) {
-			if (value === null) {
-				shape[key] = "null"
-			} else if (Array.isArray(value)) {
-				shape[key] = `array[${value.length}]`
-			} else if (typeof value === "object") {
-				shape[key] = `object{${Object.keys(value).join(",")}}`
-			} else {
-				shape[key] = typeof value
-			}
-		}
-
-		return shape
+		debugLog(message, data)
 	}
 
 	private suppressNodeWarnings(): void {
@@ -204,6 +176,17 @@ export class ExtensionHost extends EventEmitter {
 		}
 	}
 
+	/**
+	 * Create a unique ephemeral storage directory in the system temp folder.
+	 * This directory will be cleaned up when dispose() is called.
+	 */
+	private async createEphemeralStorageDir(): Promise<string> {
+		const uniqueId = `${Date.now()}-${Math.random().toString(36).slice(2, 11)}`
+		const tmpDir = path.join(os.tmpdir(), `roo-cli-${uniqueId}`)
+		await fs.promises.mkdir(tmpDir, { recursive: true })
+		return tmpDir
+	}
+
 	async activate(): Promise<void> {
 		// Suppress Node.js warnings (like MaxListenersExceededWarning) before anything else
 		this.suppressNodeWarnings()
@@ -219,12 +202,20 @@ export class ExtensionHost extends EventEmitter {
 			throw new Error(`Extension bundle not found at: ${bundlePath}`)
 		}
 
+		// Create ephemeral storage directory if ephemeral mode is enabled
+		let storageDir: string | undefined
+
+		if (this.options.ephemeral) {
+			storageDir = await this.createEphemeralStorageDir()
+			this.ephemeralStorageDir = storageDir
+		}
+
 		// 1. Create VSCode API mock
 		this.vscode = createVSCodeAPI(
 			this.options.extensionPath,
 			this.options.workspacePath,
 			undefined, // identity
-			{ appRoot: CLI_PACKAGE_ROOT }, // options - point appRoot to CLI package for ripgrep
+			{ appRoot: CLI_PACKAGE_ROOT, storageDir }, // options - point appRoot to CLI package for ripgrep, custom storageDir for ephemeral mode
 		)
 
 		// 2. Set global vscode reference for the extension
@@ -332,7 +323,7 @@ export class ExtensionHost extends EventEmitter {
 	/**
 	 * Send a message to the extension (simulating webview -> extension communication).
 	 */
-	sendToExtension(message: unknown): void {
+	sendToExtension(message: WebviewMessage): void {
 		if (!this.isWebviewReady) {
 			this.pendingMessages.push(message)
 			return
@@ -554,99 +545,55 @@ export class ExtensionHost extends EventEmitter {
 			})
 		}
 
-		// Set up message listener for extension responses
-		this.setupMessageListener()
+		// Should this only be done once?
+		this.messageListener = (message: ExtensionMessage) => this.handleExtensionMessage(message)
+		this.on("extensionWebviewMessage", this.messageListener)
+
+		let defaultSettings: RooCodeSettings
 
-		// Configure approval settings based on mode
-		// In non-interactive mode (-y flag), enable auto-approval for everything
-		// In interactive mode (default), we'll prompt the user for each action
 		if (this.options.nonInteractive) {
-			const settings: RooCodeSettings = {
+			defaultSettings = {
 				autoApprovalEnabled: true,
 				alwaysAllowReadOnly: true,
 				alwaysAllowReadOnlyOutsideWorkspace: true,
 				alwaysAllowWrite: true,
 				alwaysAllowWriteOutsideWorkspace: true,
-				alwaysAllowWriteProtected: false, // Keep protected files safe.
+				alwaysAllowWriteProtected: false,
 				alwaysAllowBrowser: true,
 				alwaysAllowMcp: true,
 				alwaysAllowModeSwitch: true,
 				alwaysAllowSubtasks: true,
 				alwaysAllowExecute: true,
 				alwaysAllowFollowupQuestions: true,
+				// NOTE: Setting to 0 should disable extension's internal timeout,
+				// but we need to verify this is working correctly.
+				followupAutoApproveTimeoutMs: 0,
 				allowedCommands: ["*"],
 				commandExecutionTimeout: 20,
 				enableCheckpoints: false, // Checkpoints disabled until CLI UI is implemented.
 			}
-
-			this.applyRuntimeSettings(settings)
-			this.sendToExtension({ type: "updateSettings", updatedSettings: settings })
-			await new Promise<void>((resolve) => setTimeout(resolve, 100))
 		} else {
-			const settings: RooCodeSettings = {
+			defaultSettings = {
 				autoApprovalEnabled: false,
-				enableCheckpoints: false, // Checkpoints disabled until CLI UI is implemented.
+				enableCheckpoints: false,
 			}
-
-			this.applyRuntimeSettings(settings)
-			this.sendToExtension({ type: "updateSettings", updatedSettings: settings })
-			await new Promise<void>((resolve) => setTimeout(resolve, 100))
 		}
 
-		// Always send API configuration - it may include API key from environment variables
-		const apiConfig = this.buildApiConfiguration()
-		this.sendToExtension({ type: "updateSettings", updatedSettings: apiConfig })
+		const settings = { ...defaultSettings, ...this.buildApiConfiguration() }
+		this.applyRuntimeSettings(settings)
+
+		this.sendToExtension({
+			type: "updateSettings",
+			updatedSettings: settings,
+		})
+
 		await new Promise<void>((resolve) => setTimeout(resolve, 100))
 
 		this.sendToExtension({ type: "newTask", text: prompt })
 		await this.waitForCompletion()
 	}
 
-	/**
-	 * Set up listener for messages from the extension
-	 */
-	private setupMessageListener(): void {
-		this.messageListener = (message: ExtensionMessage) => this.handleExtensionMessage(message)
-		this.on("extensionWebviewMessage", this.messageListener)
-	}
-
 	private handleExtensionMessage(msg: ExtensionMessage): void {
-		// Log all incoming messages for debugging
-		this.log(`[MSG] type=${msg.type}`, this.getMessageShape(msg))
-
-		// For state messages, log additional details about the state
-		if (msg.type === "state" && msg.state) {
-			const state = msg.state
-			// Extract model ID based on provider (different providers use different fields)
-			const apiConfig = state.apiConfiguration
-			let modelId = apiConfig?.apiModelId
-
-			if (apiConfig?.apiProvider === "openrouter") {
-				modelId = apiConfig?.openRouterModelId
-			} else if (apiConfig?.apiProvider === "openai") {
-				modelId = apiConfig?.openAiModelId
-			} else if (apiConfig?.apiProvider === "ollama") {
-				modelId = apiConfig?.ollamaModelId
-			}
-
-			this.log(`[STATE] mode=${state.mode}, clineMessages=${state.clineMessages?.length || 0}`, {
-				apiProvider: apiConfig?.apiProvider,
-				modelId: modelId,
-				mode: state.mode,
-				cliProvider: this.options.apiProvider,
-				cliModel: this.options.model,
-			})
-
-			// Log any ask messages in the state that might indicate resume
-			if (state.clineMessages) {
-				for (const clineMsg of state.clineMessages) {
-					if (clineMsg?.ask === "resume_task" || clineMsg?.ask === "resume_completed_task") {
-						this.log(`[RESUME DETECTED] ask=${clineMsg.ask}, ts=${clineMsg.ts}`)
-					}
-				}
-			}
-		}
-
 		switch (msg.type) {
 			case "state":
 				this.handleStateMessage(msg)
@@ -658,12 +605,11 @@ export class ExtensionHost extends EventEmitter {
 				break
 
 			case "modes":
-				// Forward modes list to the TUI.
-				this.emit("extensionWebviewMessage", msg)
+				// Forward modes list to the TUI via a dedicated event.
+				// DO NOT emit to "extensionWebviewMessage" - that would create an infinite loop
+				// since messageListener listens on that event and calls this function.
+				this.emit("modesUpdated", msg)
 				break
-
-			default:
-			// NO-OP
 		}
 	}
 
@@ -752,29 +698,11 @@ export class ExtensionHost extends EventEmitter {
 		// Track current mode for mode switch detection (in tool execution).
 		const newMode = state.mode
 
-		if (newMode && this.currentMode !== null && this.currentMode !== newMode) {
-			this.log(`[MODE CHANGE] from=${this.currentMode} to=${newMode}, re-applying CLI settings`)
-			const updatedSettings = this.buildApiConfiguration()
-			this.sendToExtension({ type: "updateSettings", updatedSettings })
-		}
-
 		if (newMode) {
 			this.currentMode = newMode
 		}
 
-		// Detect when the model in state differs from CLI-specified model.
-		// This catches task resume scenarios where the extension loads stored apiConfiguration
-		// which may differ from CLI-provided settings. We re-apply CLI settings proactively.
-		const apiConfig = state.apiConfiguration as Record<string, unknown> | undefined
-		const stateModelId = this.getStateModelId(apiConfig)
-		const expectedModelId = this.getExpectedModelId()
-
-		if (expectedModelId && stateModelId && stateModelId !== expectedModelId) {
-			this.log(`[MODEL MISMATCH] state has ${stateModelId}, CLI expects ${expectedModelId}, re-applying settings`)
-			const updatedSettings = this.buildApiConfiguration()
-			this.sendToExtension({ type: "updateSettings", updatedSettings })
-		}
-
+		// Why do we do this?
 		const clineMessages = state.clineMessages
 
 		if (clineMessages && clineMessages.length > 0) {
@@ -807,28 +735,19 @@ export class ExtensionHost extends EventEmitter {
 	 * Handle messageUpdated - individual streaming updates for a single message
 	 * This is where real-time streaming happens!
 	 */
-	private handleMessageUpdated(msg: ExtensionMessage): void {
-		const clineMessage = msg.clineMessage
+	private handleMessageUpdated({ clineMessage: msg }: ExtensionMessage): void {
+		// if (msg?.ask) {
+		// 	this.log(`[MSG] ts=${msg.ts}, ask=${msg.ask} -> ${msg.partial ? "partial" : msg.text}`)
+		// } else if (msg?.say) {
+		// 	this.log(`[MSG] ts=${msg.ts}, say=${msg.say} -> ${msg.partial ? "partial" : msg.text}`)
+		// } else if (msg) {
+		// 	this.log(`[MSG] ts=${msg.ts}, type=${msg.type}, text=${msg.text}`)
+		// }
 
-		if (!clineMessage) {
-			return
-		}
-
-		const ts = clineMessage.ts
-		const isPartial = clineMessage.partial
-		const text = clineMessage.text
-		const type = clineMessage.type
-		const say = clineMessage.say
-		const ask = clineMessage.ask
-
-		if (!ts) {
-			return
-		}
-
-		if (type === "say" && say && typeof text === "string") {
-			this.handleSayMessage(ts, say, text, isPartial)
-		} else if (type === "ask" && ask && typeof text === "string") {
-			this.handleAskMessage(ts, ask, text, isPartial)
+		if (msg?.type === "say" && msg.say && typeof msg.text === "string") {
+			this.handleSayMessage(msg.ts, msg.say, msg.text, msg.partial)
+		} else if (msg?.type === "ask" && msg.ask && typeof msg.text === "string") {
+			this.handleAskMessage(msg.ts, msg.ask, msg.text, msg.partial)
 		}
 	}
 
@@ -903,6 +822,7 @@ export class ExtensionHost extends EventEmitter {
 							const delta = text.slice(streamed.text.length)
 							this.writeStream(delta)
 						}
+
 						this.finishStream(ts)
 					} else {
 						// Not streamed yet - output complete message
@@ -1005,37 +925,40 @@ export class ExtensionHost extends EventEmitter {
 	 * In non-interactive mode: auto-approve (handled by extension settings)
 	 */
 	private handleAskMessage(ts: number, ask: string, text: string, isPartial: boolean | undefined): void {
-		// Special handling for command_output - stream it in real-time
-		// This needs to happen before the isPartial skip
+		// Special handling for command_output - stream it in real-time.
+		// This needs to happen before the isPartial skip.
 		if (ask === "command_output") {
 			this.handleCommandOutputAsk(ts, text, isPartial)
 			return
 		}
 
-		// Skip partial messages - wait for the complete ask
+		// Skip partial messages - wait for the complete ask.
 		if (isPartial) {
 			return
 		}
 
-		// Check if we already handled this ask
+		// Check if we already handled this ask.
 		if (this.pendingAsks.has(ts)) {
 			return
 		}
 
-		// In non-interactive mode, the extension's auto-approval settings handle everything
-		// We just need to display the action being taken
+		// IMPORTANT: Check disableOutput FIRST, before nonInteractive!
+		// In TUI mode (disableOutput=true), don't handle asks here - let the TUI handle them.
+		// The TUI listens to the same extensionWebviewMessage events and renders its own UI.
+		// If we don't check this first, the non-interactive handler would capture stdin input
+		// that's meant for the TUI (e.g., arrow keys show as "[B[B[B[B" escape codes).
+		if (this.options.disableOutput) {
+			return
+		}
+
+		// In non-interactive mode (without TUI), the extension's auto-approval settings handle
+		// most things, but followup questions need special handling with timeout.
 		if (this.options.nonInteractive) {
 			this.handleAskMessageNonInteractive(ts, ask, text)
 			return
 		}
 
-		// In TUI mode (disableOutput), don't handle asks here - let the TUI handle them
-		// The TUI listens to the same extensionWebviewMessage events and renders its own UI
-		if (this.options.disableOutput) {
-			return
-		}
-
-		// Interactive mode - prompt user for input
+		// Interactive mode - prompt user for input.
 		this.handleAskMessageInteractive(ts, ask, text)
 	}
 
@@ -1070,9 +993,12 @@ export class ExtensionHost extends EventEmitter {
 
 			case "tool":
 				if (!alreadyDisplayed && text) {
+					let toolInfo
+					let toolName
+
 					try {
-						const toolInfo = JSON.parse(text)
-						const toolName = toolInfo.tool || "unknown"
+						toolInfo = JSON.parse(text)
+						toolName = toolInfo.tool || "unknown"
 						this.output(`\n[tool] ${toolName}`)
 
 						// Display all tool parameters (excluding 'tool' which is the name).
@@ -1241,8 +1167,10 @@ export class ExtensionHost extends EventEmitter {
 
 			// Check if user entered a number corresponding to a suggestion
 			const num = parseInt(responseText, 10)
+
 			if (!isNaN(num) && num >= 1 && num <= suggestions.length) {
 				const selectedSuggestion = suggestions[num - 1]
+
 				if (selectedSuggestion) {
 					responseText = selectedSuggestion.answer || String(selectedSuggestion)
 					this.output(`Selected: ${responseText}`)
@@ -1267,8 +1195,9 @@ export class ExtensionHost extends EventEmitter {
 
 	/**
 	 * Handle followup questions with a timeout (for non-interactive mode)
-	 * Shows the prompt but auto-selects the first option after 10 seconds
+	 * Shows the prompt but auto-selects the first option after the timeout
 	 * if the user doesn't type anything. Cancels the timeout on any keypress.
+	 * Default timeout is 60 seconds, configurable via followupAutoApproveTimeoutMs.
 	 */
 	private async handleFollowupQuestionWithTimeout(ts: number, text: string): Promise<void> {
 		let question = text
@@ -1289,33 +1218,40 @@ export class ExtensionHost extends EventEmitter {
 		// Show numbered suggestions
 		if (suggestions.length > 0) {
 			this.output("\nSuggested answers:")
+
 			suggestions.forEach((suggestion, index) => {
 				const suggestionText = suggestion.answer || String(suggestion)
 				const modeHint = suggestion.mode ? ` (mode: ${suggestion.mode})` : ""
 				this.output(`  ${index + 1}. ${suggestionText}${modeHint}`)
 			})
+
 			this.output("")
 		}
 
-		// Default to first suggestion or empty string
+		// Default to first suggestion or empty string.
 		const firstSuggestion = suggestions.length > 0 ? suggestions[0] : null
 		const defaultAnswer = firstSuggestion?.answer ?? ""
 
+		// Default timeout is 10 seconds for testing (will be configurable later).
+		const timeoutMs = 60_000
+
 		try {
 			const answer = await this.promptForInputWithTimeout(
 				suggestions.length > 0
-					? `Enter number (1-${suggestions.length}) or type your answer (auto-select in 10s): `
-					: "Your answer (auto-select in 10s): ",
-				10000, // 10 second timeout
+					? `Enter number (1-${suggestions.length}) or type your answer (auto-select in ${Math.round(timeoutMs / 1000)}s): `
+					: `Your answer (auto-select in ${Math.round(timeoutMs / 1000)}s): `,
+				timeoutMs,
 				defaultAnswer,
 			)
 
 			let responseText = answer.trim()
 
-			// Check if user entered a number corresponding to a suggestion
+			// Check if user entered a number corresponding to a suggestion.
 			const num = parseInt(responseText, 10)
+
 			if (!isNaN(num) && num >= 1 && num <= suggestions.length) {
 				const selectedSuggestion = suggestions[num - 1]
+
 				if (selectedSuggestion) {
 					responseText = selectedSuggestion.answer || String(selectedSuggestion)
 					this.output(`Selected: ${responseText}`)
@@ -1323,8 +1259,8 @@ export class ExtensionHost extends EventEmitter {
 			}
 
 			this.sendFollowupResponse(responseText)
-		} catch {
-			// If prompt fails, use default
+		} catch (_error) {
+			// If prompt fails, use default.
 			this.output(`[Using default: ${defaultAnswer || "(empty)"}]`)
 			this.sendFollowupResponse(defaultAnswer)
 		}
@@ -1339,15 +1275,18 @@ export class ExtensionHost extends EventEmitter {
 		return new Promise((resolve) => {
 			// Temporarily restore console for interactive prompts
 			const wasQuiet = this.options.quiet
+
 			if (wasQuiet) {
 				this.restoreConsole()
 			}
 
 			// Put stdin in raw mode to detect individual keypresses
 			const wasRaw = process.stdin.isRaw
+
 			if (process.stdin.isTTY) {
 				process.stdin.setRawMode(true)
 			}
+
 			process.stdin.resume()
 
 			let inputBuffer = ""
@@ -1371,10 +1310,13 @@ export class ExtensionHost extends EventEmitter {
 			const cleanup = () => {
 				clearTimeout(timeout)
 				process.stdin.removeListener("data", onData)
+
 				if (process.stdin.isTTY && wasRaw !== undefined) {
 					process.stdin.setRawMode(wasRaw)
 				}
+
 				process.stdin.pause()
+
 				if (wasQuiet) {
 					this.setupQuietMode()
 				}
@@ -1486,13 +1428,14 @@ export class ExtensionHost extends EventEmitter {
 		try {
 			const approved = await this.promptForYesNo("Approve this action? (y/n): ")
 			this.sendApprovalResponse(approved)
-			// Note: Mode switch detection and API config re-application is handled in handleStateMessage
-			// This works for both interactive and non-interactive (auto-approved) modes
+			// Note: Mode switch detection and API config re-application is handled in handleStateMessage.
+			// This works for both interactive and non-interactive (auto-approved) modes.
 		} catch {
 			this.output("[Defaulting to: no]")
 			this.sendApprovalResponse(false)
 		}
-		// Note: Don't delete from pendingAsks - see handleFollowupQuestion comment
+
+		// Note: Don't delete from pendingAsks - see handleFollowupQuestion comment.
 	}
 
 	/**
@@ -1776,22 +1719,22 @@ export class ExtensionHost extends EventEmitter {
 	 * Clean up resources
 	 */
 	async dispose(): Promise<void> {
-		// Clear pending asks
+		// Clear pending asks.
 		this.pendingAsks.clear()
 
-		// Close readline interface if open
+		// Close readline interface if open.
 		if (this.rl) {
 			this.rl.close()
 			this.rl = null
 		}
 
-		// Remove message listener
+		// Remove message listener.
 		if (this.messageListener) {
 			this.off("extensionWebviewMessage", this.messageListener)
 			this.messageListener = null
 		}
 
-		// Deactivate extension if it has a deactivate function
+		// Deactivate extension if it has a deactivate function.
 		if (this.extensionModule?.deactivate) {
 			try {
 				await this.extensionModule.deactivate()
@@ -1800,17 +1743,27 @@ export class ExtensionHost extends EventEmitter {
 			}
 		}
 
-		// Clear references
+		// Clear references.
 		this.vscode = null
 		this.extensionModule = null
 		this.extensionAPI = null
 		this.webviewProviders.clear()
 
-		// Clear globals
+		// Clear globals.
 		delete (global as Record<string, unknown>).vscode
 		delete (global as Record<string, unknown>).__extensionHost
 
-		// Restore console if it was suppressed
+		// Restore console if it was suppressed.
 		this.restoreConsole()
+
+		// Clean up ephemeral storage directory if it exists.
+		if (this.ephemeralStorageDir) {
+			try {
+				await fs.promises.rm(this.ephemeralStorageDir, { recursive: true, force: true })
+				this.ephemeralStorageDir = null
+			} catch (_error) {
+				// NO-OP
+			}
+		}
 	}
 }
diff --git a/apps/cli/src/index.ts b/apps/cli/src/index.ts
index 1eead41a17..7c9a0e7e7c 100644
--- a/apps/cli/src/index.ts
+++ b/apps/cli/src/index.ts
@@ -58,6 +58,7 @@ program
 		"Reasoning effort level (unspecified, disabled, none, minimal, low, medium, high, xhigh)",
 		DEFAULTS.reasoningEffort,
 	)
+	.option("--ephemeral", "Run without persisting state (uses temporary storage)", false)
 	.option("--no-tui", "Disable TUI, use plain text output")
 	.action(
 		async (
@@ -74,6 +75,7 @@ program
 				model?: string
 				mode?: string
 				reasoningEffort?: ReasoningEffortExtended | "unspecified" | "disabled"
+				ephemeral: boolean
 				tui: boolean
 			},
 		) => {
@@ -153,6 +155,7 @@ program
 						quiet: boolean
 						nonInteractive: boolean
 						disableOutput: boolean
+						ephemeral?: boolean
 					}) => {
 						return new ExtensionHost({
 							mode: opts.mode,
@@ -169,6 +172,7 @@ program
 							quiet: opts.quiet,
 							nonInteractive: opts.nonInteractive,
 							disableOutput: opts.disableOutput,
+							ephemeral: opts.ephemeral,
 						})
 					}
 
@@ -186,6 +190,7 @@ program
 							debug: options.debug,
 							exitOnComplete: options.exitOnComplete,
 							reasoningEffort: options.reasoningEffort,
+							ephemeral: options.ephemeral,
 							createExtensionHost: createExtensionHost,
 							version: packageJson.version,
 						}),
@@ -219,6 +224,7 @@ program
 					verbose: options.debug,
 					quiet: !options.verbose && !options.debug,
 					nonInteractive: options.yes,
+					ephemeral: options.ephemeral,
 				})
 
 				// Handle SIGINT (Ctrl+C)
diff --git a/apps/cli/src/ui/App.tsx b/apps/cli/src/ui/App.tsx
index 167f82e5f0..ff43b7b886 100644
--- a/apps/cli/src/ui/App.tsx
+++ b/apps/cli/src/ui/App.tsx
@@ -4,9 +4,9 @@ import { useState, useEffect, useCallback, useRef, useMemo } from "react"
 import { EventEmitter } from "events"
 import { randomUUID } from "crypto"
 
+import type { ClineMessage, TodoItem, WebviewMessage } from "@roo-code/types"
 // Import only message-utils to avoid custom-tools dependencies (execa/child_process)
 import { consolidateTokenUsage, consolidateApiRequests, consolidateCommands } from "@roo-code/core/message-utils"
-import type { ClineMessage, TodoItem } from "@roo-code/types"
 
 import { useCLIStore } from "./store.js"
 import { getContextWindow } from "../utils/getContextWindow.js"
@@ -56,7 +56,7 @@ const PICKER_HEIGHT = 10 // Max height for picker when open
 interface ExtensionHostInterface extends EventEmitter {
 	activate(): Promise<void>
 	runTask(prompt: string): Promise<void>
-	sendToExtension(message: unknown): void
+	sendToExtension(message: WebviewMessage): void
 	dispose(): Promise<void>
 }
 
@@ -77,6 +77,7 @@ interface ExtensionHostOptions {
 	quiet: boolean
 	nonInteractive: boolean
 	disableOutput: boolean
+	ephemeral?: boolean
 }
 
 /**
@@ -155,6 +156,7 @@ function AppInner({
 	debug,
 	exitOnComplete,
 	reasoningEffort,
+	ephemeral,
 	createExtensionHost,
 	version,
 }: TUIAppProps) {
@@ -228,6 +230,11 @@ function AppInner({
 	const exitHintTimeout = useRef<NodeJS.Timeout | null>(null)
 	const pendingExit = useRef(false)
 
+	// Countdown timer for auto-accepting followup questions (10 seconds for testing)
+	const FOLLOWUP_TIMEOUT_SECONDS = 10
+	const [countdownSeconds, setCountdownSeconds] = useState<number | null>(null)
+	const countdownIntervalRef = useRef<NodeJS.Timeout | null>(null)
+
 	// Track whether user wants to type custom response for followup questions
 	const [showCustomInput, setShowCustomInput] = useState(false)
 	// Ref to track transition state (handles async state update timing)
@@ -313,10 +320,7 @@ function AppInner({
 			return
 		}
 
-		hostRef.current.sendToExtension({
-			type: "searchFiles",
-			query,
-		})
+		hostRef.current.sendToExtension({ type: "searchFiles", query })
 	}, [])
 
 	// Create autocomplete triggers
@@ -413,9 +417,64 @@ function AppInner({
 			if (exitHintTimeout.current) {
 				clearTimeout(exitHintTimeout.current)
 			}
+			if (countdownIntervalRef.current) {
+				clearInterval(countdownIntervalRef.current)
+			}
 		}
 	}, [])
 
+	// Countdown timer for auto-accepting followup questions
+	// Start countdown when a followup question with suggestions appears
+	useEffect(() => {
+		// Clear any existing countdown
+		if (countdownIntervalRef.current) {
+			clearInterval(countdownIntervalRef.current)
+			countdownIntervalRef.current = null
+		}
+
+		// Only start countdown for followup questions with suggestions (not custom input mode)
+		if (
+			pendingAsk?.type === "followup" &&
+			pendingAsk.suggestions &&
+			pendingAsk.suggestions.length > 0 &&
+			!showCustomInput
+		) {
+			// Start countdown
+			setCountdownSeconds(FOLLOWUP_TIMEOUT_SECONDS)
+
+			countdownIntervalRef.current = setInterval(() => {
+				setCountdownSeconds((prev) => {
+					if (prev === null || prev <= 1) {
+						// Time's up! Auto-select first option
+						if (countdownIntervalRef.current) {
+							clearInterval(countdownIntervalRef.current)
+							countdownIntervalRef.current = null
+						}
+						// Auto-submit the first suggestion
+						if (pendingAsk?.suggestions && pendingAsk.suggestions.length > 0) {
+							const firstSuggestion = pendingAsk.suggestions[0]
+							if (firstSuggestion) {
+								handleSubmit(firstSuggestion.answer)
+							}
+						}
+						return null
+					}
+					return prev - 1
+				})
+			}, 1000)
+		} else {
+			// No countdown needed
+			setCountdownSeconds(null)
+		}
+
+		return () => {
+			if (countdownIntervalRef.current) {
+				clearInterval(countdownIntervalRef.current)
+				countdownIntervalRef.current = null
+			}
+		}
+	}, [pendingAsk?.id, pendingAsk?.type, showCustomInput]) // Re-run when pendingAsk changes or user switches to custom input
+
 	// Refresh search results when fileSearchResults changes while file picker is open
 	// This handles the async timing where API results arrive after initial search
 	// IMPORTANT: Only run when fileSearchResults array identity changes (new API response)
@@ -774,6 +833,7 @@ function AppInner({
 					quiet: !verbose && !debug,
 					nonInteractive,
 					disableOutput: true,
+					ephemeral,
 				})
 
 				hostRef.current = host
@@ -943,6 +1003,28 @@ function AppInner({
 		}
 	})
 
+	// Cancel countdown timer when user navigates in the followup suggestion menu
+	// This provides better UX - any user interaction cancels the auto-accept timer
+	const showFollowupSuggestions =
+		pendingAsk?.type === "followup" &&
+		pendingAsk.suggestions &&
+		pendingAsk.suggestions.length > 0 &&
+		!showCustomInput
+
+	useInput((_input, key) => {
+		// Only handle when followup suggestions are shown and countdown is active
+		if (showFollowupSuggestions && countdownSeconds !== null) {
+			// Cancel countdown on any arrow key navigation
+			if (key.upArrow || key.downArrow) {
+				if (countdownIntervalRef.current) {
+					clearInterval(countdownIntervalRef.current)
+					countdownIntervalRef.current = null
+				}
+				setCountdownSeconds(null)
+			}
+		}
+	})
+
 	// Handle picker state changes from AutocompleteInput
 	// eslint-disable-next-line @typescript-eslint/no-explicit-any
 	const handlePickerStateChange = useCallback((state: AutocompletePickerState<any>) => setPickerState(state), [])
@@ -999,9 +1081,10 @@ function AppInner({
 	}
 
 	// Status bar content
+	// Don't show spinner when waiting for user input (pendingAsk is set)
 	const statusBarMessage = showExitHint ? (
 		<Text color="yellow">Press Ctrl+C again to exit</Text>
-	) : isLoading ? (
+	) : isLoading && !pendingAsk ? (
 		<Box>
 			<LoadingText>{view === "ToolUse" ? "Using tool" : "Thinking"}</LoadingText>
 			<Text color={theme.dimText}> • </Text>
@@ -1082,6 +1165,13 @@ function AppInner({
 										if (showCustomInput || isTransitioningToCustomInput.current) return
 
 										if (value === "__CUSTOM__") {
+											// Clear countdown timer synchronously BEFORE state update
+											// This prevents race condition where interval fires before useEffect cleanup
+											if (countdownIntervalRef.current) {
+												clearInterval(countdownIntervalRef.current)
+												countdownIntervalRef.current = null
+											}
+											setCountdownSeconds(null)
 											isTransitioningToCustomInput.current = true
 											setShowCustomInput(true)
 										} else if (value.trim()) {
@@ -1090,7 +1180,12 @@ function AppInner({
 									}}
 								/>
 								<HorizontalLine active={true} />
-								<Text color={theme.dimText}>↑↓ navigate • Enter select</Text>
+								<Text color={theme.dimText}>
+									↑↓ navigate • Enter select
+									{countdownSeconds !== null && (
+										<Text color="yellow"> • Auto-select in {countdownSeconds}s</Text>
+									)}
+								</Text>
 							</Box>
 						) : (
 							<Box flexDirection="column" marginTop={1}>
diff --git a/apps/cli/src/ui/types.ts b/apps/cli/src/ui/types.ts
index 5f708bf4c6..a9e5ada1cb 100644
--- a/apps/cli/src/ui/types.ts
+++ b/apps/cli/src/ui/types.ts
@@ -72,6 +72,8 @@ export interface AppProps {
 	debug: boolean
 	exitOnComplete: boolean
 	reasoningEffort?: string
+	/** Run in ephemeral mode - no state persists after this session */
+	ephemeral?: boolean
 	version: string
 }
 
diff --git a/packages/core/package.json b/packages/core/package.json
index 41f2dfa95c..ad25cc863d 100644
--- a/packages/core/package.json
+++ b/packages/core/package.json
@@ -5,7 +5,8 @@
 	"type": "module",
 	"exports": {
 		".": "./src/index.ts",
-		"./message-utils": "./src/message-utils/index.ts"
+		"./message-utils": "./src/message-utils/index.ts",
+		"./debug-log": "./src/debug-log/index.ts"
 	},
 	"scripts": {
 		"lint": "eslint src --ext=ts --max-warnings=0",
diff --git a/packages/core/src/debug-log/index.ts b/packages/core/src/debug-log/index.ts
new file mode 100644
index 0000000000..797ec60ba9
--- /dev/null
+++ b/packages/core/src/debug-log/index.ts
@@ -0,0 +1,91 @@
+/**
+ * File-based debug logging utility
+ *
+ * This writes logs to ~/.roo/cli-debug.log, avoiding stdout/stderr
+ * which would break TUI applications. The log format is timestamped JSON.
+ *
+ * Usage:
+ *   import { debugLog, DebugLogger } from "@roo-code/core/debug-log"
+ *
+ *   // Simple logging
+ *   debugLog("handleModeSwitch", { mode: newMode, configId })
+ *
+ *   // Or create a named logger for a component
+ *   const log = new DebugLogger("ClineProvider")
+ *   log.info("handleModeSwitch", { mode: newMode })
+ */
+
+import * as fs from "fs"
+import * as path from "path"
+import * as os from "os"
+
+const DEBUG_LOG_PATH = path.join(os.homedir(), ".roo", "cli-debug.log")
+
+/**
+ * Simple file-based debug log function.
+ * Writes timestamped entries to ~/.roo/cli-debug.log
+ */
+export function debugLog(message: string, data?: unknown): void {
+	try {
+		const logDir = path.dirname(DEBUG_LOG_PATH)
+
+		if (!fs.existsSync(logDir)) {
+			fs.mkdirSync(logDir, { recursive: true })
+		}
+
+		const timestamp = new Date().toISOString()
+
+		const entry = data
+			? `[${timestamp}] ${message}: ${JSON.stringify(data, null, 2)}\n`
+			: `[${timestamp}] ${message}\n`
+
+		fs.appendFileSync(DEBUG_LOG_PATH, entry)
+	} catch {
+		// NO-OP - don't let logging errors break functionality
+	}
+}
+
+/**
+ * Debug logger with component context.
+ * Prefixes all messages with the component name.
+ */
+export class DebugLogger {
+	private component: string
+
+	constructor(component: string) {
+		this.component = component
+	}
+
+	/**
+	 * Log a debug message with optional data
+	 */
+	debug(message: string, data?: unknown): void {
+		debugLog(`[${this.component}] ${message}`, data)
+	}
+
+	/**
+	 * Alias for debug
+	 */
+	info(message: string, data?: unknown): void {
+		this.debug(message, data)
+	}
+
+	/**
+	 * Log a warning
+	 */
+	warn(message: string, data?: unknown): void {
+		debugLog(`[${this.component}] WARN: ${message}`, data)
+	}
+
+	/**
+	 * Log an error
+	 */
+	error(message: string, data?: unknown): void {
+		debugLog(`[${this.component}] ERROR: ${message}`, data)
+	}
+}
+
+/**
+ * Pre-configured logger for provider/mode debugging
+ */
+export const providerDebugLog = new DebugLogger("ProviderSettings")
diff --git a/packages/types/src/vscode-extension-host.ts b/packages/types/src/vscode-extension-host.ts
index 68e132f572..81018ee44a 100644
--- a/packages/types/src/vscode-extension-host.ts
+++ b/packages/types/src/vscode-extension-host.ts
@@ -1,11 +1,18 @@
-import type { GlobalSettings } from "./global-settings.js"
+import { z } from "zod"
+
+import type { GlobalSettings, RooCodeSettings } from "./global-settings.js"
 import type { ProviderSettings, ProviderSettingsEntry } from "./provider-settings.js"
 import type { HistoryItem } from "./history.js"
-import type { ModeConfig } from "./mode.js"
+import type { ModeConfig, PromptComponent } from "./mode.js"
 import type { TelemetrySetting } from "./telemetry.js"
 import type { Experiments } from "./experiment.js"
 import type { ClineMessage, QueuedMessage } from "./message.js"
-import type { MarketplaceItem, MarketplaceInstalledMetadata } from "./marketplace.js"
+import {
+	type MarketplaceItem,
+	type MarketplaceInstalledMetadata,
+	type InstallMarketplaceItemOptions,
+	marketplaceItemSchema,
+} from "./marketplace.js"
 import type { TodoItem } from "./todo.js"
 import type { CloudUserInfo, CloudOrganizationMembership, OrganizationAllowList, ShareVisibility } from "./cloud.js"
 import type { SerializedCustomToolDefinition } from "./custom-tool.js"
@@ -13,7 +20,10 @@ import type { GitCommit } from "./git.js"
 import type { McpServer } from "./mcp.js"
 import type { ModelRecord, RouterModels } from "./model.js"
 
-// Represents JSON data that is sent from extension to the webview or cli.
+/**
+ * ExtensionMessage
+ * Extension -> Webview | CLI
+ */
 export interface ExtensionMessage {
 	type:
 		| "action"
@@ -325,3 +335,310 @@ export interface Command {
 	description?: string
 	argumentHint?: string
 }
+
+/**
+ * WebviewMessage
+ * Webview | CLI -> Extension
+ */
+
+export type ClineAskResponse = "yesButtonClicked" | "noButtonClicked" | "messageResponse" | "objectResponse"
+
+export type AudioType = "notification" | "celebration" | "progress_loop"
+
+export interface UpdateTodoListPayload {
+	// eslint-disable-next-line @typescript-eslint/no-explicit-any
+	todos: any[]
+}
+
+export type EditQueuedMessagePayload = Pick<QueuedMessage, "id" | "text" | "images">
+
+export interface WebviewMessage {
+	type:
+		| "updateTodoList"
+		| "deleteMultipleTasksWithIds"
+		| "currentApiConfigName"
+		| "saveApiConfiguration"
+		| "upsertApiConfiguration"
+		| "deleteApiConfiguration"
+		| "loadApiConfiguration"
+		| "loadApiConfigurationById"
+		| "renameApiConfiguration"
+		| "getListApiConfiguration"
+		| "customInstructions"
+		| "webviewDidLaunch"
+		| "newTask"
+		| "askResponse"
+		| "terminalOperation"
+		| "clearTask"
+		| "didShowAnnouncement"
+		| "selectImages"
+		| "exportCurrentTask"
+		| "shareCurrentTask"
+		| "showTaskWithId"
+		| "deleteTaskWithId"
+		| "exportTaskWithId"
+		| "importSettings"
+		| "exportSettings"
+		| "resetState"
+		| "flushRouterModels"
+		| "requestRouterModels"
+		| "requestOpenAiModels"
+		| "requestOllamaModels"
+		| "requestLmStudioModels"
+		| "requestRooModels"
+		| "requestRooCreditBalance"
+		| "requestVsCodeLmModels"
+		| "requestHuggingFaceModels"
+		| "openImage"
+		| "saveImage"
+		| "openFile"
+		| "openMention"
+		| "cancelTask"
+		| "cancelAutoApproval"
+		| "updateVSCodeSetting"
+		| "getVSCodeSetting"
+		| "vsCodeSetting"
+		| "updateCondensingPrompt"
+		| "playSound"
+		| "playTts"
+		| "stopTts"
+		| "ttsEnabled"
+		| "ttsSpeed"
+		| "openKeyboardShortcuts"
+		| "openMcpSettings"
+		| "openProjectMcpSettings"
+		| "restartMcpServer"
+		| "refreshAllMcpServers"
+		| "toggleToolAlwaysAllow"
+		| "toggleToolEnabledForPrompt"
+		| "toggleMcpServer"
+		| "updateMcpTimeout"
+		| "enhancePrompt"
+		| "enhancedPrompt"
+		| "draggedImages"
+		| "deleteMessage"
+		| "deleteMessageConfirm"
+		| "submitEditedMessage"
+		| "editMessageConfirm"
+		| "enableMcpServerCreation"
+		| "remoteControlEnabled"
+		| "taskSyncEnabled"
+		| "searchCommits"
+		| "setApiConfigPassword"
+		| "mode"
+		| "updatePrompt"
+		| "getSystemPrompt"
+		| "copySystemPrompt"
+		| "systemPrompt"
+		| "enhancementApiConfigId"
+		| "autoApprovalEnabled"
+		| "updateCustomMode"
+		| "deleteCustomMode"
+		| "setopenAiCustomModelInfo"
+		| "openCustomModesSettings"
+		| "checkpointDiff"
+		| "checkpointRestore"
+		| "deleteMcpServer"
+		| "codebaseIndexEnabled"
+		| "telemetrySetting"
+		| "testBrowserConnection"
+		| "browserConnectionResult"
+		| "searchFiles"
+		| "toggleApiConfigPin"
+		| "hasOpenedModeSelector"
+		| "clearCloudAuthSkipModel"
+		| "cloudButtonClicked"
+		| "rooCloudSignIn"
+		| "cloudLandingPageSignIn"
+		| "rooCloudSignOut"
+		| "rooCloudManualUrl"
+		| "claudeCodeSignIn"
+		| "claudeCodeSignOut"
+		| "switchOrganization"
+		| "condenseTaskContextRequest"
+		| "requestIndexingStatus"
+		| "startIndexing"
+		| "clearIndexData"
+		| "indexingStatusUpdate"
+		| "indexCleared"
+		| "focusPanelRequest"
+		| "openExternal"
+		| "filterMarketplaceItems"
+		| "marketplaceButtonClicked"
+		| "installMarketplaceItem"
+		| "installMarketplaceItemWithParameters"
+		| "cancelMarketplaceInstall"
+		| "removeInstalledMarketplaceItem"
+		| "marketplaceInstallResult"
+		| "fetchMarketplaceData"
+		| "switchTab"
+		| "shareTaskSuccess"
+		| "exportMode"
+		| "exportModeResult"
+		| "importMode"
+		| "importModeResult"
+		| "checkRulesDirectory"
+		| "checkRulesDirectoryResult"
+		| "saveCodeIndexSettingsAtomic"
+		| "requestCodeIndexSecretStatus"
+		| "requestCommands"
+		| "openCommandFile"
+		| "deleteCommand"
+		| "createCommand"
+		| "insertTextIntoTextarea"
+		| "showMdmAuthRequiredNotification"
+		| "imageGenerationSettings"
+		| "queueMessage"
+		| "removeQueuedMessage"
+		| "editQueuedMessage"
+		| "dismissUpsell"
+		| "getDismissedUpsells"
+		| "updateSettings"
+		| "allowedCommands"
+		| "deniedCommands"
+		| "killBrowserSession"
+		| "openBrowserSessionPanel"
+		| "showBrowserSessionPanelAtStep"
+		| "refreshBrowserSessionPanel"
+		| "browserPanelDidLaunch"
+		| "openDebugApiHistory"
+		| "openDebugUiHistory"
+		| "downloadErrorDiagnostics"
+		| "requestClaudeCodeRateLimits"
+		| "refreshCustomTools"
+		| "requestModes"
+		| "switchMode"
+	text?: string
+	editedMessageContent?: string
+	tab?: "settings" | "history" | "mcp" | "modes" | "chat" | "marketplace" | "cloud"
+	disabled?: boolean
+	context?: string
+	dataUri?: string
+	askResponse?: ClineAskResponse
+	apiConfiguration?: ProviderSettings
+	images?: string[]
+	bool?: boolean
+	value?: number
+	stepIndex?: number
+	isLaunchAction?: boolean
+	forceShow?: boolean
+	commands?: string[]
+	audioType?: AudioType
+	serverName?: string
+	toolName?: string
+	alwaysAllow?: boolean
+	isEnabled?: boolean
+	mode?: string
+	promptMode?: string | "enhance"
+	customPrompt?: PromptComponent
+	dataUrls?: string[]
+	// eslint-disable-next-line @typescript-eslint/no-explicit-any
+	values?: Record<string, any>
+	query?: string
+	setting?: string
+	slug?: string
+	modeConfig?: ModeConfig
+	timeout?: number
+	payload?: WebViewMessagePayload
+	source?: "global" | "project"
+	requestId?: string
+	ids?: string[]
+	hasSystemPromptOverride?: boolean
+	terminalOperation?: "continue" | "abort"
+	messageTs?: number
+	restoreCheckpoint?: boolean
+	historyPreviewCollapsed?: boolean
+	filters?: { type?: string; search?: string; tags?: string[] }
+	// eslint-disable-next-line @typescript-eslint/no-explicit-any
+	settings?: any
+	url?: string // For openExternal
+	mpItem?: MarketplaceItem
+	mpInstallOptions?: InstallMarketplaceItemOptions
+	// eslint-disable-next-line @typescript-eslint/no-explicit-any
+	config?: Record<string, any> // Add config to the payload
+	visibility?: ShareVisibility // For share visibility
+	hasContent?: boolean // For checkRulesDirectoryResult
+	checkOnly?: boolean // For deleteCustomMode check
+	upsellId?: string // For dismissUpsell
+	list?: string[] // For dismissedUpsells response
+	organizationId?: string | null // For organization switching
+	useProviderSignup?: boolean // For rooCloudSignIn to use provider signup flow
+	codeIndexSettings?: {
+		// Global state settings
+		codebaseIndexEnabled: boolean
+		codebaseIndexQdrantUrl: string
+		codebaseIndexEmbedderProvider:
+			| "openai"
+			| "ollama"
+			| "openai-compatible"
+			| "gemini"
+			| "mistral"
+			| "vercel-ai-gateway"
+			| "bedrock"
+			| "openrouter"
+		codebaseIndexEmbedderBaseUrl?: string
+		codebaseIndexEmbedderModelId: string
+		codebaseIndexEmbedderModelDimension?: number // Generic dimension for all providers
+		codebaseIndexOpenAiCompatibleBaseUrl?: string
+		codebaseIndexBedrockRegion?: string
+		codebaseIndexBedrockProfile?: string
+		codebaseIndexSearchMaxResults?: number
+		codebaseIndexSearchMinScore?: number
+		codebaseIndexOpenRouterSpecificProvider?: string // OpenRouter provider routing
+
+		// Secret settings
+		codeIndexOpenAiKey?: string
+		codeIndexQdrantApiKey?: string
+		codebaseIndexOpenAiCompatibleApiKey?: string
+		codebaseIndexGeminiApiKey?: string
+		codebaseIndexMistralApiKey?: string
+		codebaseIndexVercelAiGatewayApiKey?: string
+		codebaseIndexOpenRouterApiKey?: string
+	}
+	updatedSettings?: RooCodeSettings
+}
+
+export const checkoutDiffPayloadSchema = z.object({
+	ts: z.number().optional(),
+	previousCommitHash: z.string().optional(),
+	commitHash: z.string(),
+	mode: z.enum(["full", "checkpoint", "from-init", "to-current"]),
+})
+
+export type CheckpointDiffPayload = z.infer<typeof checkoutDiffPayloadSchema>
+
+export const checkoutRestorePayloadSchema = z.object({
+	ts: z.number(),
+	commitHash: z.string(),
+	mode: z.enum(["preview", "restore"]),
+})
+
+export type CheckpointRestorePayload = z.infer<typeof checkoutRestorePayloadSchema>
+
+export interface IndexingStatusPayload {
+	state: "Standby" | "Indexing" | "Indexed" | "Error"
+	message: string
+}
+
+export interface IndexClearedPayload {
+	success: boolean
+	error?: string
+}
+
+export const installMarketplaceItemWithParametersPayloadSchema = z.object({
+	item: marketplaceItemSchema,
+	parameters: z.record(z.string(), z.any()),
+})
+
+export type InstallMarketplaceItemWithParametersPayload = z.infer<
+	typeof installMarketplaceItemWithParametersPayloadSchema
+>
+
+export type WebViewMessagePayload =
+	| CheckpointDiffPayload
+	| CheckpointRestorePayload
+	| IndexingStatusPayload
+	| IndexClearedPayload
+	| InstallMarketplaceItemWithParametersPayload
+	| UpdateTodoListPayload
+	| EditQueuedMessagePayload
diff --git a/packages/vscode-shim/src/api/create-vscode-api-mock.ts b/packages/vscode-shim/src/api/create-vscode-api-mock.ts
index 1eb22d3675..fd4a94a8a6 100644
--- a/packages/vscode-shim/src/api/create-vscode-api-mock.ts
+++ b/packages/vscode-shim/src/api/create-vscode-api-mock.ts
@@ -68,6 +68,13 @@ export interface VSCodeAPIMockOptions {
 	 * Defaults to the directory containing this module.
 	 */
 	appRoot?: string
+
+	/**
+	 * Custom storage directory for persistent state.
+	 * Defaults to ~/.vscode-mock.
+	 * Set to a temp directory for ephemeral/no-persist mode.
+	 */
+	storageDir?: string
 }
 
 /**
@@ -82,6 +89,7 @@ export function createVSCodeAPIMock(
 	const context = new ExtensionContextImpl({
 		extensionPath: extensionRootPath,
 		workspacePath: workspacePath,
+		storageDir: options?.storageDir,
 	})
 	const workspace = new WorkspaceAPI(workspacePath, context)
 	const window = new WindowAPI()
diff --git a/src/core/config/ProviderSettingsManager.ts b/src/core/config/ProviderSettingsManager.ts
index 420ab332b2..e7ae0d96b5 100644
--- a/src/core/config/ProviderSettingsManager.ts
+++ b/src/core/config/ProviderSettingsManager.ts
@@ -2,6 +2,8 @@ import { ExtensionContext } from "vscode"
 import { z, ZodError } from "zod"
 import deepEqual from "fast-deep-equal"
 
+import { debugLog } from "../../utils/debug-log"
+
 import {
 	type ProviderSettingsWithId,
 	providerSettingsWithIdSchema,
@@ -377,12 +379,21 @@ export class ProviderSettingsManager {
 			return await this.lock(async () => {
 				const providerProfiles = await this.load()
 
-				return Object.entries(providerProfiles.apiConfigs).map(([name, apiConfig]) => ({
+				const configs = Object.entries(providerProfiles.apiConfigs).map(([name, apiConfig]) => ({
 					name,
 					id: apiConfig.id || "",
 					apiProvider: apiConfig.apiProvider,
 					modelId: this.cleanModelId(getModelId(apiConfig)),
 				}))
+
+				// DEBUG: Log listed configs
+				debugLog("[ProviderSettingsManager.listConfig]", {
+					configCount: configs.length,
+					configs: configs.map((c) => ({ name: c.name, id: c.id, provider: c.apiProvider })),
+					modeApiConfigs: providerProfiles.modeApiConfigs,
+				})
+
+				return configs
 			})
 		} catch (error) {
 			throw new Error(`Failed to list configs: ${error}`)
@@ -458,16 +469,40 @@ export class ProviderSettingsManager {
 	public async activateProfile(
 		params: { name: string } | { id: string },
 	): Promise<ProviderSettingsWithId & { name: string }> {
+		// DEBUG: Log entry point
+		debugLog("[ProviderSettingsManager.activateProfile] START", { params })
+
 		const { name, ...providerSettings } = await this.getProfile(params)
 
+		// DEBUG: Log what was retrieved from getProfile
+		debugLog("[ProviderSettingsManager.activateProfile] getProfile result", {
+			name,
+			id: providerSettings.id,
+			apiProvider: providerSettings.apiProvider,
+			hasSettings: Object.keys(providerSettings).length > 0,
+			settingsKeys: Object.keys(providerSettings).filter(
+				(k) => providerSettings[k as keyof typeof providerSettings] !== undefined,
+			),
+		})
+
 		try {
 			return await this.lock(async () => {
 				const providerProfiles = await this.load()
 				providerProfiles.currentApiConfigName = name
 				await this.store(providerProfiles)
+
+				debugLog("[ProviderSettingsManager.activateProfile] END - profile activated", {
+					name,
+					id: providerSettings.id,
+				})
+
 				return { name, ...providerSettings }
 			})
 		} catch (error) {
+			debugLog("[ProviderSettingsManager.activateProfile] ERROR", {
+				params,
+				error: error instanceof Error ? error.message : String(error),
+			})
 			throw new Error(`Failed to activate profile: ${error instanceof Error ? error.message : error}`)
 		}
 	}
@@ -536,10 +571,27 @@ export class ProviderSettingsManager {
 	public async getModeConfigId(mode: Mode) {
 		try {
 			return await this.lock(async () => {
-				const { modeApiConfigs } = await this.load()
-				return modeApiConfigs?.[mode]
+				const providerProfiles = await this.load()
+				const configId = providerProfiles.modeApiConfigs?.[mode]
+
+				// DEBUG: Log mode config lookup
+				debugLog("[ProviderSettingsManager.getModeConfigId]", {
+					mode,
+					configId,
+					allModeApiConfigs: providerProfiles.modeApiConfigs,
+					availableConfigIds: Object.entries(providerProfiles.apiConfigs).map(([name, c]) => ({
+						name,
+						id: c.id,
+					})),
+				})
+
+				return configId
 			})
 		} catch (error) {
+			debugLog("[ProviderSettingsManager.getModeConfigId] ERROR", {
+				mode,
+				error: error instanceof Error ? error.message : String(error),
+			})
 			throw new Error(`Failed to get mode config: ${error}`)
 		}
 	}
@@ -610,7 +662,15 @@ export class ProviderSettingsManager {
 		try {
 			const content = await this.context.secrets.get(this.secretsKey)
 
+			// DEBUG: Log raw secrets content
+			debugLog("[ProviderSettingsManager.load] secrets.get result", {
+				secretsKey: this.secretsKey,
+				hasContent: !!content,
+				contentLength: content?.length ?? 0,
+			})
+
 			if (!content) {
+				debugLog("[ProviderSettingsManager.load] returning default profiles (no content found)")
 				return this.defaultProviderProfiles
 			}
 
@@ -631,12 +691,31 @@ export class ProviderSettingsManager {
 				{} as Record<string, ProviderSettingsWithId>,
 			)
 
-			return {
+			const result = {
 				...providerProfiles,
 				apiConfigs: Object.fromEntries(
 					Object.entries(apiConfigs).filter(([_, apiConfig]) => apiConfig !== null),
 				),
 			}
+
+			// DEBUG: Log loaded profiles summary
+			debugLog("[ProviderSettingsManager.load] loaded profiles", {
+				currentApiConfigName: result.currentApiConfigName,
+				apiConfigNames: Object.keys(result.apiConfigs),
+				modeApiConfigs: result.modeApiConfigs,
+				configDetails: Object.entries(result.apiConfigs).map(([name, config]) => ({
+					name,
+					id: config.id,
+					apiProvider: config.apiProvider,
+					hasApiKey: !!(
+						(config as any)?.apiKey ||
+						(config as any)?.openRouterApiKey ||
+						(config as any)?.requestyApiKey
+					),
+				})),
+			})
+
+			return result
 		} catch (error) {
 			if (error instanceof ZodError) {
 				TelemetryService.instance.captureSchemaValidationError({
@@ -645,6 +724,10 @@ export class ProviderSettingsManager {
 				})
 			}
 
+			debugLog("[ProviderSettingsManager.load] ERROR", {
+				error: error instanceof Error ? error.message : String(error),
+			})
+
 			throw new Error(`Failed to read provider profiles from secrets: ${error}`)
 		}
 	}
diff --git a/src/core/webview/ClineProvider.ts b/src/core/webview/ClineProvider.ts
index 1c5ceb64ae..42f53b7a67 100644
--- a/src/core/webview/ClineProvider.ts
+++ b/src/core/webview/ClineProvider.ts
@@ -3,6 +3,8 @@ import * as path from "path"
 import fs from "fs/promises"
 import EventEmitter from "events"
 
+import { debugLog, DebugLogger } from "../../utils/debug-log"
+
 import { Anthropic } from "@anthropic-ai/sdk"
 import delay from "delay"
 import axios from "axios"
@@ -904,7 +906,24 @@ export class ClineProvider
 
 				if (profile?.name) {
 					try {
-						await this.activateProviderProfile({ name: profile.name })
+						// Check if the profile has actual API configuration (not just an id).
+						// In CLI mode, the ProviderSettingsManager may return empty default profiles
+						// that only contain 'id' and 'name' fields. Activating such a profile would
+						// overwrite the CLI's working API configuration with empty settings.
+						const fullProfile = await this.providerSettingsManager.getProfile({ name: profile.name })
+						const hasActualSettings = !!fullProfile.apiProvider
+
+						if (hasActualSettings) {
+							await this.activateProviderProfile({ name: profile.name })
+						} else {
+							debugLog(
+								"[createTaskWithHistoryItem] SKIPPING profile activation - profile has no apiProvider",
+								{
+									savedConfigId,
+									profileName: profile.name,
+								},
+							)
+						}
 					} catch (error) {
 						// Log the error but continue with task restoration.
 						this.log(
@@ -1241,6 +1260,15 @@ export class ClineProvider
 	 * @param newMode The mode to switch to
 	 */
 	public async handleModeSwitch(newMode: Mode) {
+		// DEBUG: Log entry point with current state
+		const currentApiConfigName = this.getGlobalState("currentApiConfigName")
+		const currentMode = this.getGlobalState("mode")
+		debugLog("[handleModeSwitch] START", {
+			newMode,
+			currentMode,
+			currentApiConfigName,
+		})
+
 		const task = this.getCurrentTask()
 
 		if (task) {
@@ -1279,6 +1307,14 @@ export class ClineProvider
 		const savedConfigId = await this.providerSettingsManager.getModeConfigId(newMode)
 		const listApiConfig = await this.providerSettingsManager.listConfig()
 
+		// DEBUG: Log mode config lookup results
+		debugLog("[handleModeSwitch] getModeConfigId result", {
+			newMode,
+			savedConfigId,
+			listApiConfigCount: listApiConfig.length,
+			listApiConfigNames: listApiConfig.map((c) => ({ name: c.name, id: c.id, provider: c.apiProvider })),
+		})
+
 		// Update listApiConfigMeta first to ensure UI has latest data.
 		await this.updateGlobalState("listApiConfigMeta", listApiConfig)
 
@@ -1286,22 +1322,80 @@ export class ClineProvider
 		if (savedConfigId) {
 			const profile = listApiConfig.find(({ id }) => id === savedConfigId)
 
+			// DEBUG: Log profile activation attempt
+			debugLog("[handleModeSwitch] activating saved config", {
+				savedConfigId,
+				foundProfile: profile ? { name: profile.name, id: profile.id, provider: profile.apiProvider } : null,
+			})
+
 			if (profile?.name) {
-				await this.activateProviderProfile({ name: profile.name })
+				// Check if the profile has actual API configuration (not just an id).
+				// In CLI mode, the ProviderSettingsManager may return empty default profiles
+				// that only contain 'id' and 'name' fields. Activating such a profile would
+				// overwrite the CLI's working API configuration with empty settings.
+				// Skip activation if the profile has no apiProvider set - this indicates
+				// an unconfigured/empty profile.
+				const fullProfile = await this.providerSettingsManager.getProfile({ name: profile.name })
+				const hasActualSettings = !!fullProfile.apiProvider
+
+				if (hasActualSettings) {
+					await this.activateProviderProfile({ name: profile.name })
+				} else {
+					debugLog(
+						"[handleModeSwitch] SKIPPING profile activation - profile has no apiProvider (CLI mode workaround)",
+						{
+							savedConfigId,
+							profileName: profile.name,
+							profileKeys: Object.keys(fullProfile).filter(
+								(k) => fullProfile[k as keyof typeof fullProfile] !== undefined,
+							),
+						},
+					)
+				}
+			} else {
+				debugLog("[handleModeSwitch] WARNING: savedConfigId exists but profile not found in listApiConfig", {
+					savedConfigId,
+					availableIds: listApiConfig.map((c) => c.id),
+				})
 			}
 		} else {
 			// If no saved config for this mode, save current config as default.
-			const currentApiConfigName = this.getGlobalState("currentApiConfigName")
+			const currentApiConfigNameAfter = this.getGlobalState("currentApiConfigName")
 
-			if (currentApiConfigName) {
-				const config = listApiConfig.find((c) => c.name === currentApiConfigName)
+			// DEBUG: Log no saved config case
+			debugLog("[handleModeSwitch] no saved config for mode, using current", {
+				newMode,
+				currentApiConfigNameAfter,
+			})
+
+			if (currentApiConfigNameAfter) {
+				const config = listApiConfig.find((c) => c.name === currentApiConfigNameAfter)
 
 				if (config?.id) {
+					debugLog("[handleModeSwitch] saving current config as mode default", {
+						newMode,
+						configId: config.id,
+						configName: config.name,
+					})
 					await this.providerSettingsManager.setModeConfig(newMode, config.id)
 				}
 			}
 		}
 
+		// DEBUG: Log final state after mode switch
+		const finalState = await this.getState()
+		debugLog("[handleModeSwitch] END - final state", {
+			newMode,
+			finalApiProvider: finalState.apiConfiguration?.apiProvider,
+			finalApiConfigName: finalState.currentApiConfigName,
+			// Check various provider API keys to see if any are set
+			hasAnyApiKey: !!(
+				(finalState.apiConfiguration as any)?.apiKey ||
+				(finalState.apiConfiguration as any)?.openRouterApiKey ||
+				(finalState.apiConfiguration as any)?.requestyApiKey
+			),
+		})
+
 		await this.postStateToWebview()
 	}
 
@@ -1441,8 +1535,27 @@ export class ClineProvider
 	}
 
 	async activateProviderProfile(args: { name: string } | { id: string }) {
+		// DEBUG: Log entry point
+		debugLog("[activateProviderProfile] START", { args })
+
 		const { name, id, ...providerSettings } = await this.providerSettingsManager.activateProfile(args)
 
+		// DEBUG: Log what was returned from activateProfile
+		debugLog("[activateProviderProfile] activateProfile result", {
+			name,
+			id,
+			apiProvider: providerSettings.apiProvider,
+			hasApiKey: !!(
+				(providerSettings as any)?.apiKey ||
+				(providerSettings as any)?.openRouterApiKey ||
+				(providerSettings as any)?.requestyApiKey
+			),
+			// Log all keys that have values (but not the values themselves for security)
+			settingsKeys: Object.keys(providerSettings).filter(
+				(k) => providerSettings[k as keyof typeof providerSettings] !== undefined,
+			),
+		})
+
 		// See `upsertProviderProfile` for a description of what this is doing.
 		await Promise.all([
 			this.contextProxy.setValue("listApiConfigMeta", await this.providerSettingsManager.listConfig()),
@@ -1452,6 +1565,9 @@ export class ClineProvider
 
 		const { mode } = await this.getState()
 
+		// DEBUG: Log mode config update
+		debugLog("[activateProviderProfile] setting mode config", { mode, id })
+
 		if (id) {
 			await this.providerSettingsManager.setModeConfig(mode, id)
 		}
@@ -1460,6 +1576,18 @@ export class ClineProvider
 
 		await this.postStateToWebview()
 
+		// DEBUG: Log final state
+		const finalState = this.contextProxy.getProviderSettings()
+		debugLog("[activateProviderProfile] END - final provider settings", {
+			name,
+			apiProvider: finalState.apiProvider,
+			hasApiKey: !!(
+				(finalState as any)?.apiKey ||
+				(finalState as any)?.openRouterApiKey ||
+				(finalState as any)?.requestyApiKey
+			),
+		})
+
 		if (providerSettings.apiProvider) {
 			this.emit(RooCodeEventName.ProviderProfileChanged, { name, provider: providerSettings.apiProvider })
 		}
diff --git a/src/core/webview/webviewMessageHandler.ts b/src/core/webview/webviewMessageHandler.ts
index 5505f77c55..4b0281e9e3 100644
--- a/src/core/webview/webviewMessageHandler.ts
+++ b/src/core/webview/webviewMessageHandler.ts
@@ -13,9 +13,13 @@ import {
 	type TelemetrySetting,
 	type UserSettingsConfig,
 	type ModelRecord,
+	type WebviewMessage,
+	type EditQueuedMessagePayload,
 	TelemetryEventName,
 	RooCodeSettings,
 	ExperimentId,
+	checkoutDiffPayloadSchema,
+	checkoutRestorePayloadSchema,
 } from "@roo-code/types"
 import { customToolRegistry } from "@roo-code/core"
 import { CloudService } from "@roo-code/cloud"
@@ -33,12 +37,6 @@ import { Package } from "../../shared/package"
 import { type RouterName, toRouterName } from "../../shared/api"
 import { MessageEnhancer } from "./messageEnhancer"
 
-import {
-	type WebviewMessage,
-	type EditQueuedMessagePayload,
-	checkoutDiffPayloadSchema,
-	checkoutRestorePayloadSchema,
-} from "../../shared/WebviewMessage"
 import { checkExistKey } from "../../shared/checkExistApiConfig"
 import { experimentDefault } from "../../shared/experiments"
 import { Terminal } from "../../integrations/terminal/Terminal"
diff --git a/src/shared/WebviewMessage.ts b/src/shared/WebviewMessage.ts
index e915d0d6be..9ec3eba5aa 100644
--- a/src/shared/WebviewMessage.ts
+++ b/src/shared/WebviewMessage.ts
@@ -1,315 +1,3 @@
-import { z } from "zod"
-
-import {
-	type RooCodeSettings,
-	type ProviderSettings,
-	type PromptComponent,
-	type ModeConfig,
-	type InstallMarketplaceItemOptions,
-	type MarketplaceItem,
-	type ShareVisibility,
-	type QueuedMessage,
-	marketplaceItemSchema,
-} from "@roo-code/types"
-
-import { Mode } from "./modes"
+export type { WebviewMessage, WebViewMessagePayload } from "@roo-code/types"
 
 export type ClineAskResponse = "yesButtonClicked" | "noButtonClicked" | "messageResponse" | "objectResponse"
-
-export type PromptMode = Mode | "enhance"
-
-export type AudioType = "notification" | "celebration" | "progress_loop"
-
-export interface UpdateTodoListPayload {
-	todos: any[]
-}
-
-export type EditQueuedMessagePayload = Pick<QueuedMessage, "id" | "text" | "images">
-
-export interface WebviewMessage {
-	type:
-		| "updateTodoList"
-		| "deleteMultipleTasksWithIds"
-		| "currentApiConfigName"
-		| "saveApiConfiguration"
-		| "upsertApiConfiguration"
-		| "deleteApiConfiguration"
-		| "loadApiConfiguration"
-		| "loadApiConfigurationById"
-		| "renameApiConfiguration"
-		| "getListApiConfiguration"
-		| "customInstructions"
-		| "webviewDidLaunch"
-		| "newTask"
-		| "askResponse"
-		| "terminalOperation"
-		| "clearTask"
-		| "didShowAnnouncement"
-		| "selectImages"
-		| "exportCurrentTask"
-		| "shareCurrentTask"
-		| "showTaskWithId"
-		| "deleteTaskWithId"
-		| "exportTaskWithId"
-		| "importSettings"
-		| "exportSettings"
-		| "resetState"
-		| "flushRouterModels"
-		| "requestRouterModels"
-		| "requestOpenAiModels"
-		| "requestOllamaModels"
-		| "requestLmStudioModels"
-		| "requestRooModels"
-		| "requestRooCreditBalance"
-		| "requestVsCodeLmModels"
-		| "requestHuggingFaceModels"
-		| "openImage"
-		| "saveImage"
-		| "openFile"
-		| "openMention"
-		| "cancelTask"
-		| "cancelAutoApproval"
-		| "updateVSCodeSetting"
-		| "getVSCodeSetting"
-		| "vsCodeSetting"
-		| "updateCondensingPrompt"
-		| "playSound"
-		| "playTts"
-		| "stopTts"
-		| "ttsEnabled"
-		| "ttsSpeed"
-		| "openKeyboardShortcuts"
-		| "openMcpSettings"
-		| "openProjectMcpSettings"
-		| "restartMcpServer"
-		| "refreshAllMcpServers"
-		| "toggleToolAlwaysAllow"
-		| "toggleToolEnabledForPrompt"
-		| "toggleMcpServer"
-		| "updateMcpTimeout"
-		| "enhancePrompt"
-		| "enhancedPrompt"
-		| "draggedImages"
-		| "deleteMessage"
-		| "deleteMessageConfirm"
-		| "submitEditedMessage"
-		| "editMessageConfirm"
-		| "enableMcpServerCreation"
-		| "remoteControlEnabled"
-		| "taskSyncEnabled"
-		| "searchCommits"
-		| "setApiConfigPassword"
-		| "mode"
-		| "updatePrompt"
-		| "getSystemPrompt"
-		| "copySystemPrompt"
-		| "systemPrompt"
-		| "enhancementApiConfigId"
-		| "autoApprovalEnabled"
-		| "updateCustomMode"
-		| "deleteCustomMode"
-		| "setopenAiCustomModelInfo"
-		| "openCustomModesSettings"
-		| "checkpointDiff"
-		| "checkpointRestore"
-		| "deleteMcpServer"
-		| "codebaseIndexEnabled"
-		| "telemetrySetting"
-		| "testBrowserConnection"
-		| "browserConnectionResult"
-		| "searchFiles"
-		| "toggleApiConfigPin"
-		| "hasOpenedModeSelector"
-		| "clearCloudAuthSkipModel"
-		| "cloudButtonClicked"
-		| "rooCloudSignIn"
-		| "cloudLandingPageSignIn"
-		| "rooCloudSignOut"
-		| "rooCloudManualUrl"
-		| "claudeCodeSignIn"
-		| "claudeCodeSignOut"
-		| "switchOrganization"
-		| "condenseTaskContextRequest"
-		| "requestIndexingStatus"
-		| "startIndexing"
-		| "clearIndexData"
-		| "indexingStatusUpdate"
-		| "indexCleared"
-		| "focusPanelRequest"
-		| "openExternal"
-		| "filterMarketplaceItems"
-		| "marketplaceButtonClicked"
-		| "installMarketplaceItem"
-		| "installMarketplaceItemWithParameters"
-		| "cancelMarketplaceInstall"
-		| "removeInstalledMarketplaceItem"
-		| "marketplaceInstallResult"
-		| "fetchMarketplaceData"
-		| "switchTab"
-		| "shareTaskSuccess"
-		| "exportMode"
-		| "exportModeResult"
-		| "importMode"
-		| "importModeResult"
-		| "checkRulesDirectory"
-		| "checkRulesDirectoryResult"
-		| "saveCodeIndexSettingsAtomic"
-		| "requestCodeIndexSecretStatus"
-		| "requestCommands"
-		| "openCommandFile"
-		| "deleteCommand"
-		| "createCommand"
-		| "insertTextIntoTextarea"
-		| "showMdmAuthRequiredNotification"
-		| "imageGenerationSettings"
-		| "queueMessage"
-		| "removeQueuedMessage"
-		| "editQueuedMessage"
-		| "dismissUpsell"
-		| "getDismissedUpsells"
-		| "updateSettings"
-		| "allowedCommands"
-		| "deniedCommands"
-		| "killBrowserSession"
-		| "openBrowserSessionPanel"
-		| "showBrowserSessionPanelAtStep"
-		| "refreshBrowserSessionPanel"
-		| "browserPanelDidLaunch"
-		| "openDebugApiHistory"
-		| "openDebugUiHistory"
-		| "downloadErrorDiagnostics"
-		| "requestClaudeCodeRateLimits"
-		| "refreshCustomTools"
-		| "requestModes"
-		| "switchMode"
-	text?: string
-	editedMessageContent?: string
-	tab?: "settings" | "history" | "mcp" | "modes" | "chat" | "marketplace" | "cloud"
-	disabled?: boolean
-	context?: string
-	dataUri?: string
-	askResponse?: ClineAskResponse
-	apiConfiguration?: ProviderSettings
-	images?: string[]
-	bool?: boolean
-	value?: number
-	stepIndex?: number
-	isLaunchAction?: boolean
-	forceShow?: boolean
-	commands?: string[]
-	audioType?: AudioType
-	serverName?: string
-	toolName?: string
-	alwaysAllow?: boolean
-	isEnabled?: boolean
-	mode?: Mode
-	promptMode?: PromptMode
-	customPrompt?: PromptComponent
-	dataUrls?: string[]
-	values?: Record<string, any>
-	query?: string
-	setting?: string
-	slug?: string
-	modeConfig?: ModeConfig
-	timeout?: number
-	payload?: WebViewMessagePayload
-	source?: "global" | "project"
-	requestId?: string
-	ids?: string[]
-	hasSystemPromptOverride?: boolean
-	terminalOperation?: "continue" | "abort"
-	messageTs?: number
-	restoreCheckpoint?: boolean
-	historyPreviewCollapsed?: boolean
-	filters?: { type?: string; search?: string; tags?: string[] }
-	settings?: any
-	url?: string // For openExternal
-	mpItem?: MarketplaceItem
-	mpInstallOptions?: InstallMarketplaceItemOptions
-	config?: Record<string, any> // Add config to the payload
-	visibility?: ShareVisibility // For share visibility
-	hasContent?: boolean // For checkRulesDirectoryResult
-	checkOnly?: boolean // For deleteCustomMode check
-	upsellId?: string // For dismissUpsell
-	list?: string[] // For dismissedUpsells response
-	organizationId?: string | null // For organization switching
-	useProviderSignup?: boolean // For rooCloudSignIn to use provider signup flow
-	codeIndexSettings?: {
-		// Global state settings
-		codebaseIndexEnabled: boolean
-		codebaseIndexQdrantUrl: string
-		codebaseIndexEmbedderProvider:
-			| "openai"
-			| "ollama"
-			| "openai-compatible"
-			| "gemini"
-			| "mistral"
-			| "vercel-ai-gateway"
-			| "bedrock"
-			| "openrouter"
-		codebaseIndexEmbedderBaseUrl?: string
-		codebaseIndexEmbedderModelId: string
-		codebaseIndexEmbedderModelDimension?: number // Generic dimension for all providers
-		codebaseIndexOpenAiCompatibleBaseUrl?: string
-		codebaseIndexBedrockRegion?: string
-		codebaseIndexBedrockProfile?: string
-		codebaseIndexSearchMaxResults?: number
-		codebaseIndexSearchMinScore?: number
-		codebaseIndexOpenRouterSpecificProvider?: string // OpenRouter provider routing
-
-		// Secret settings
-		codeIndexOpenAiKey?: string
-		codeIndexQdrantApiKey?: string
-		codebaseIndexOpenAiCompatibleApiKey?: string
-		codebaseIndexGeminiApiKey?: string
-		codebaseIndexMistralApiKey?: string
-		codebaseIndexVercelAiGatewayApiKey?: string
-		codebaseIndexOpenRouterApiKey?: string
-	}
-	updatedSettings?: RooCodeSettings
-}
-
-export const checkoutDiffPayloadSchema = z.object({
-	ts: z.number().optional(),
-	previousCommitHash: z.string().optional(),
-	commitHash: z.string(),
-	mode: z.enum(["full", "checkpoint", "from-init", "to-current"]),
-})
-
-export type CheckpointDiffPayload = z.infer<typeof checkoutDiffPayloadSchema>
-
-export const checkoutRestorePayloadSchema = z.object({
-	ts: z.number(),
-	commitHash: z.string(),
-	mode: z.enum(["preview", "restore"]),
-})
-
-export type CheckpointRestorePayload = z.infer<typeof checkoutRestorePayloadSchema>
-
-export interface IndexingStatusPayload {
-	state: "Standby" | "Indexing" | "Indexed" | "Error"
-	message: string
-}
-
-export interface IndexClearedPayload {
-	success: boolean
-	error?: string
-}
-
-export const installMarketplaceItemWithParametersPayloadSchema = z.object({
-	item: marketplaceItemSchema,
-	parameters: z.record(z.string(), z.any()),
-})
-
-export type InstallMarketplaceItemWithParametersPayload = z.infer<
-	typeof installMarketplaceItemWithParametersPayloadSchema
->
-
-export type WebViewMessagePayload =
-	| CheckpointDiffPayload
-	| CheckpointRestorePayload
-	| IndexingStatusPayload
-	| IndexClearedPayload
-	| InstallMarketplaceItemWithParametersPayload
-	| UpdateTodoListPayload
-	| EditQueuedMessagePayload
diff --git a/src/utils/debug-log.ts b/src/utils/debug-log.ts
new file mode 100644
index 0000000000..3257531755
--- /dev/null
+++ b/src/utils/debug-log.ts
@@ -0,0 +1,19 @@
+/**
+ * File-based debug logging utility
+ *
+ * Re-exports from @roo-code/core/debug-log for consistency across the codebase.
+ * This writes logs to ~/.roo/cli-debug.log, avoiding stdout/stderr
+ * which would break TUI applications.
+ *
+ * Usage:
+ *   import { debugLog, DebugLogger } from "../utils/debug-log"
+ *
+ *   // Simple logging
+ *   debugLog("handleModeSwitch", { mode: newMode, configId })
+ *
+ *   // Or create a named logger for a component
+ *   const log = new DebugLogger("ClineProvider")
+ *   log.info("handleModeSwitch", { mode: newMode })
+ */
+
+export { debugLog, DebugLogger, providerDebugLog } from "@roo-code/core/debug-log"
diff --git a/webview-ui/src/components/chat/ChatView.tsx b/webview-ui/src/components/chat/ChatView.tsx
index 2b784e1fe0..e92d998d81 100644
--- a/webview-ui/src/components/chat/ChatView.tsx
+++ b/webview-ui/src/components/chat/ChatView.tsx
@@ -11,7 +11,7 @@ import { Trans } from "react-i18next"
 import { useDebounceEffect } from "@src/utils/useDebounceEffect"
 import { appendImages } from "@src/utils/imageUtils"
 
-import type { ClineAsk, ClineMessage, ExtensionMessage } from "@roo-code/types"
+import type { ClineAsk, ClineMessage, ExtensionMessage, AudioType } from "@roo-code/types"
 
 import { ClineSayTool } from "@roo/ExtensionMessage"
 import { findLast } from "@roo/array"
@@ -19,7 +19,6 @@ import { SuggestionItem } from "@roo-code/types"
 import { combineApiRequests } from "@roo/combineApiRequests"
 import { combineCommandSequences } from "@roo/combineCommandSequences"
 import { getApiMetrics } from "@roo/getApiMetrics"
-import { AudioType } from "@roo/WebviewMessage"
 import { getAllModes } from "@roo/modes"
 import { ProfileValidator } from "@roo/ProfileValidator"
 import { getLatestTodo } from "@roo/todo"