diff --git a/packages/cloud/src/index.ts b/packages/cloud/src/index.ts
index 65b92ebc13c..2ed696a03c2 100644
--- a/packages/cloud/src/index.ts
+++ b/packages/cloud/src/index.ts
@@ -6,3 +6,6 @@ export { BridgeOrchestrator } from "./bridge/index.js"
 
 export { RetryQueue } from "./retry-queue/index.js"
 export type { QueuedRequest, QueueStats, RetryQueueConfig, RetryQueueEvents } from "./retry-queue/index.js"
+
+export { RefreshTimer } from "./RefreshTimer.js"
+export type { RefreshTimerOptions } from "./RefreshTimer.js"
diff --git a/src/extension.ts b/src/extension.ts
index dcb941fa581..752906ed8cb 100644
--- a/src/extension.ts
+++ b/src/extension.ts
@@ -96,7 +96,7 @@ export async function activate(context: vscode.ExtensionContext) {
 	TerminalRegistry.initialize()
 
 	// Initialize Claude Code OAuth manager for direct API access.
-	claudeCodeOAuthManager.initialize(context)
+	await claudeCodeOAuthManager.initialize(context)
 
 	// Get default commands from configuration.
 	const defaultCommands = vscode.workspace.getConfiguration(Package.name).get<string[]>("allowedCommands") || []
@@ -424,6 +424,9 @@ export async function deactivate() {
 		await bridge.disconnect()
 	}
 
+	// Cleanup Claude Code OAuth manager
+	claudeCodeOAuthManager.dispose()
+
 	await McpServerManager.cleanup(extensionContext)
 	TelemetryService.instance.shutdown()
 	TerminalRegistry.cleanup()
diff --git a/src/integrations/claude-code/__tests__/oauth.spec.ts b/src/integrations/claude-code/__tests__/oauth.spec.ts
index 526ef2f6f7d..3d9cd01b21a 100644
--- a/src/integrations/claude-code/__tests__/oauth.spec.ts
+++ b/src/integrations/claude-code/__tests__/oauth.spec.ts
@@ -5,10 +5,22 @@ import {
 	generateUserId,
 	buildAuthorizationUrl,
 	isTokenExpired,
+	refreshAccessToken,
 	CLAUDE_CODE_OAUTH_CONFIG,
+	ClaudeCodeOAuthManager,
 	type ClaudeCodeCredentials,
 } from "../oauth"
 
+// Mock vscode module
+vi.mock("vscode", () => ({
+	window: {
+		showWarningMessage: vi.fn(),
+	},
+}))
+
+// Mock fetch for token refresh tests
+global.fetch = vi.fn()
+
 describe("Claude Code OAuth", () => {
 	describe("generateCodeVerifier", () => {
 		test("should generate a base64url encoded verifier", () => {
@@ -195,4 +207,239 @@ describe("Claude Code OAuth", () => {
 			expect(CLAUDE_CODE_OAUTH_CONFIG.callbackPort).toBe(54545)
 		})
 	})
+
+	describe("refreshAccessToken", () => {
+		beforeEach(() => {
+			vi.clearAllMocks()
+		})
+
+		test("should successfully refresh token", async () => {
+			const mockResponse = {
+				access_token: "new-access-token",
+				refresh_token: "new-refresh-token",
+				expires_in: 3600,
+				email: "test@example.com",
+			}
+
+			;(global.fetch as any).mockResolvedValue({
+				ok: true,
+				json: async () => mockResponse,
+			})
+
+			const credentials = await refreshAccessToken("old-refresh-token")
+
+			expect(credentials.access_token).toBe("new-access-token")
+			expect(credentials.refresh_token).toBe("new-refresh-token")
+			expect(credentials.email).toBe("test@example.com")
+			expect(credentials.type).toBe("claude")
+			expect(new Date(credentials.expired).getTime()).toBeGreaterThan(Date.now())
+		})
+
+		test("should throw error on failed refresh", async () => {
+			;(global.fetch as any).mockResolvedValue({
+				ok: false,
+				status: 401,
+				statusText: "Unauthorized",
+				text: async () => "Invalid refresh token",
+			})
+
+			await expect(refreshAccessToken("invalid-refresh-token")).rejects.toThrow(
+				/Token refresh failed.*401.*Unauthorized/,
+			)
+		})
+	})
+
+	describe("ClaudeCodeOAuthManager", () => {
+		let manager: ClaudeCodeOAuthManager
+		let mockContext: any
+
+		beforeEach(() => {
+			vi.clearAllMocks()
+			manager = new ClaudeCodeOAuthManager()
+			mockContext = {
+				secrets: {
+					get: vi.fn(),
+					store: vi.fn(),
+					delete: vi.fn(),
+				},
+			}
+		})
+
+		afterEach(() => {
+			manager.dispose()
+		})
+
+		describe("initialize", () => {
+			test("should initialize without credentials", async () => {
+				mockContext.secrets.get.mockResolvedValue(null)
+
+				await manager.initialize(mockContext)
+
+				expect(mockContext.secrets.get).toHaveBeenCalled()
+			})
+
+			test("should load and start refresh timer with existing credentials", async () => {
+				const futureDate = new Date(Date.now() + 60 * 60 * 1000)
+				const credentials: ClaudeCodeCredentials = {
+					type: "claude",
+					access_token: "test-token",
+					refresh_token: "test-refresh",
+					expired: futureDate.toISOString(),
+				}
+
+				mockContext.secrets.get.mockResolvedValue(JSON.stringify(credentials))
+
+				await manager.initialize(mockContext)
+
+				// Credentials should be loaded
+				expect(manager.getCredentials()).toMatchObject(credentials)
+			})
+		})
+
+		describe("getAccessToken", () => {
+			test("should return null when not authenticated", async () => {
+				mockContext.secrets.get.mockResolvedValue(null)
+				await manager.initialize(mockContext)
+
+				const token = await manager.getAccessToken()
+
+				expect(token).toBeNull()
+			})
+
+			test("should return existing valid token", async () => {
+				const futureDate = new Date(Date.now() + 60 * 60 * 1000)
+				const credentials: ClaudeCodeCredentials = {
+					type: "claude",
+					access_token: "valid-token",
+					refresh_token: "test-refresh",
+					expired: futureDate.toISOString(),
+				}
+
+				mockContext.secrets.get.mockResolvedValue(JSON.stringify(credentials))
+				await manager.initialize(mockContext)
+
+				const token = await manager.getAccessToken()
+
+				expect(token).toBe("valid-token")
+			})
+
+			test("should refresh expired token automatically", async () => {
+				const pastDate = new Date(Date.now() - 60 * 60 * 1000)
+				const credentials: ClaudeCodeCredentials = {
+					type: "claude",
+					access_token: "expired-token",
+					refresh_token: "test-refresh",
+					expired: pastDate.toISOString(),
+				}
+
+				mockContext.secrets.get.mockResolvedValue(JSON.stringify(credentials))
+
+				const mockResponse = {
+					access_token: "new-token",
+					refresh_token: "new-refresh",
+					expires_in: 3600,
+				}
+
+				;(global.fetch as any).mockResolvedValue({
+					ok: true,
+					json: async () => mockResponse,
+				})
+
+				await manager.initialize(mockContext)
+
+				const token = await manager.getAccessToken()
+
+				expect(token).toBe("new-token")
+				expect(mockContext.secrets.store).toHaveBeenCalled()
+			})
+		})
+
+		describe("saveCredentials", () => {
+			test("should save credentials and start refresh timer", async () => {
+				await manager.initialize(mockContext)
+
+				const credentials: ClaudeCodeCredentials = {
+					type: "claude",
+					access_token: "new-token",
+					refresh_token: "new-refresh",
+					expired: new Date(Date.now() + 3600 * 1000).toISOString(),
+				}
+
+				await manager.saveCredentials(credentials)
+
+				expect(mockContext.secrets.store).toHaveBeenCalledWith(
+					"claude-code-oauth-credentials",
+					JSON.stringify(credentials),
+				)
+				expect(manager.getCredentials()).toMatchObject(credentials)
+			})
+		})
+
+		describe("clearCredentials", () => {
+			test("should clear credentials and stop refresh timer", async () => {
+				const credentials: ClaudeCodeCredentials = {
+					type: "claude",
+					access_token: "test-token",
+					refresh_token: "test-refresh",
+					expired: new Date(Date.now() + 3600 * 1000).toISOString(),
+				}
+
+				mockContext.secrets.get.mockResolvedValue(JSON.stringify(credentials))
+				await manager.initialize(mockContext)
+
+				await manager.clearCredentials()
+
+				expect(mockContext.secrets.delete).toHaveBeenCalled()
+				expect(manager.getCredentials()).toBeNull()
+			})
+		})
+
+		describe("isAuthenticated", () => {
+			test("should return false when no credentials", async () => {
+				mockContext.secrets.get.mockResolvedValue(null)
+				await manager.initialize(mockContext)
+
+				const isAuth = await manager.isAuthenticated()
+
+				expect(isAuth).toBe(false)
+			})
+
+			test("should return true with valid credentials", async () => {
+				const futureDate = new Date(Date.now() + 60 * 60 * 1000)
+				const credentials: ClaudeCodeCredentials = {
+					type: "claude",
+					access_token: "valid-token",
+					refresh_token: "test-refresh",
+					expired: futureDate.toISOString(),
+				}
+
+				mockContext.secrets.get.mockResolvedValue(JSON.stringify(credentials))
+				await manager.initialize(mockContext)
+
+				const isAuth = await manager.isAuthenticated()
+
+				expect(isAuth).toBe(true)
+			})
+		})
+
+		describe("dispose", () => {
+			test("should stop refresh timer and cancel auth flow", async () => {
+				const credentials: ClaudeCodeCredentials = {
+					type: "claude",
+					access_token: "test-token",
+					refresh_token: "test-refresh",
+					expired: new Date(Date.now() + 3600 * 1000).toISOString(),
+				}
+
+				mockContext.secrets.get.mockResolvedValue(JSON.stringify(credentials))
+				await manager.initialize(mockContext)
+
+				// Should not throw
+				manager.dispose()
+
+				// Calling dispose multiple times should be safe
+				manager.dispose()
+			})
+		})
+	})
 })
diff --git a/src/integrations/claude-code/oauth.ts b/src/integrations/claude-code/oauth.ts
index 036ad70b631..46ad8750591 100644
--- a/src/integrations/claude-code/oauth.ts
+++ b/src/integrations/claude-code/oauth.ts
@@ -3,6 +3,7 @@ import * as http from "http"
 import { URL } from "url"
 import type { ExtensionContext } from "vscode"
 import { z } from "zod"
+import { RefreshTimer } from "@roo-code/cloud"
 
 // OAuth Configuration
 export const CLAUDE_CODE_OAUTH_CONFIG = {
@@ -205,12 +206,21 @@ export class ClaudeCodeOAuthManager {
 		state: string
 		server?: http.Server
 	} | null = null
+	private refreshTimer: RefreshTimer | null = null
+	private refreshAttempts: number = 0
+	private maxRefreshAttempts: number = 3
 
 	/**
 	 * Initialize the OAuth manager with VS Code extension context
 	 */
-	initialize(context: ExtensionContext): void {
+	async initialize(context: ExtensionContext): Promise<void> {
 		this.context = context
+
+		// Load existing credentials and start refresh timer if authenticated
+		await this.loadCredentials()
+		if (this.credentials) {
+			this.startRefreshTimer()
+		}
 	}
 
 	/**
@@ -246,6 +256,14 @@ export class ClaudeCodeOAuthManager {
 
 		await this.context.secrets.store(CLAUDE_CODE_CREDENTIALS_KEY, JSON.stringify(credentials))
 		this.credentials = credentials
+
+		// Reset refresh attempts on successful save
+		this.refreshAttempts = 0
+
+		// Start refresh timer if not already running
+		if (!this.refreshTimer) {
+			this.startRefreshTimer()
+		}
 	}
 
 	/**
@@ -258,6 +276,8 @@ export class ClaudeCodeOAuthManager {
 
 		await this.context.secrets.delete(CLAUDE_CODE_CREDENTIALS_KEY)
 		this.credentials = null
+		this.stopRefreshTimer()
+		this.refreshAttempts = 0
 	}
 
 	/**
@@ -278,11 +298,25 @@ export class ClaudeCodeOAuthManager {
 			try {
 				const newCredentials = await refreshAccessToken(this.credentials.refresh_token)
 				await this.saveCredentials(newCredentials)
+				console.log("[claude-code-oauth] Token refreshed successfully")
 			} catch (error) {
 				console.error("[claude-code-oauth] Failed to refresh token:", error)
-				// Clear invalid credentials
-				await this.clearCredentials()
-				return null
+
+				// Increment refresh attempts
+				this.refreshAttempts++
+
+				// Only clear credentials after max attempts to allow retry
+				if (this.refreshAttempts >= this.maxRefreshAttempts) {
+					console.error(
+						`[claude-code-oauth] Max refresh attempts (${this.maxRefreshAttempts}) reached, clearing credentials`,
+					)
+					await this.clearCredentials()
+					await this.notifyReauthRequired()
+					return null
+				}
+
+				// Don't return null immediately - let the old token be tried
+				// It might still work for some grace period
 			}
 		}
 
@@ -473,6 +507,120 @@ export class ClaudeCodeOAuthManager {
 	getCredentials(): ClaudeCodeCredentials | null {
 		return this.credentials
 	}
+
+	/**
+	 * Start the background token refresh timer
+	 * Refreshes tokens proactively before they expire
+	 */
+	private startRefreshTimer(): void {
+		// Don't start if already running
+		if (this.refreshTimer) {
+			return
+		}
+
+		this.refreshTimer = new RefreshTimer({
+			callback: async () => {
+				try {
+					await this.performBackgroundRefresh()
+					return true // Success
+				} catch (error) {
+					console.error("[claude-code-oauth] Background refresh failed:", error)
+					return false // Failure - will trigger backoff
+				}
+			},
+			// Refresh every 50 minutes (tokens typically last 1 hour, we refresh with 10min buffer)
+			successInterval: 50 * 60 * 1000,
+			initialBackoffMs: 1000,
+			maxBackoffMs: 5 * 60 * 1000, // Max 5 minutes backoff
+		})
+
+		this.refreshTimer.start()
+		console.log("[claude-code-oauth] Started background token refresh timer")
+	}
+
+	/**
+	 * Stop the background token refresh timer
+	 */
+	private stopRefreshTimer(): void {
+		if (this.refreshTimer) {
+			this.refreshTimer.stop()
+			this.refreshTimer = null
+			console.log("[claude-code-oauth] Stopped background token refresh timer")
+		}
+	}
+
+	/**
+	 * Perform a background token refresh
+	 */
+	private async performBackgroundRefresh(): Promise<void> {
+		if (!this.credentials) {
+			throw new Error("No credentials available for refresh")
+		}
+
+		// Only refresh if token is close to expiring (within 10 minutes)
+		const expiryTime = new Date(this.credentials.expired).getTime()
+		const timeUntilExpiry = expiryTime - Date.now()
+		const tenMinutes = 10 * 60 * 1000
+
+		if (timeUntilExpiry > tenMinutes) {
+			// Token is still fresh, no need to refresh yet
+			console.log(
+				`[claude-code-oauth] Token still valid for ${Math.round(timeUntilExpiry / 60000)} minutes, skipping refresh`,
+			)
+			return
+		}
+
+		console.log("[claude-code-oauth] Performing background token refresh...")
+
+		try {
+			const newCredentials = await refreshAccessToken(this.credentials.refresh_token)
+			await this.saveCredentials(newCredentials)
+			console.log("[claude-code-oauth] Background token refresh successful")
+		} catch (error) {
+			this.refreshAttempts++
+
+			if (this.refreshAttempts >= this.maxRefreshAttempts) {
+				console.error(
+					`[claude-code-oauth] Max refresh attempts (${this.maxRefreshAttempts}) reached in background refresh`,
+				)
+				await this.clearCredentials()
+				await this.notifyReauthRequired()
+				throw new Error("Failed to refresh token after multiple attempts")
+			}
+
+			throw error
+		}
+	}
+
+	/**
+	 * Notify the user that re-authentication is required
+	 */
+	private async notifyReauthRequired(): Promise<void> {
+		try {
+			const vscode = await import("vscode")
+			const action = await vscode.window.showWarningMessage(
+				"Your Claude.ai authentication has expired. Please sign in again to continue using Claude models.",
+				"Sign In",
+				"Later",
+			)
+
+			if (action === "Sign In") {
+				// Trigger the sign-in flow through the webview message handler
+				// This will be handled by the UI layer
+				console.log("[claude-code-oauth] User requested re-authentication")
+			}
+		} catch (error) {
+			console.error("[claude-code-oauth] Failed to show re-auth notification:", error)
+		}
+	}
+
+	/**
+	 * Dispose of resources (call this when extension deactivates)
+	 */
+	dispose(): void {
+		this.stopRefreshTimer()
+		this.cancelAuthorizationFlow()
+	}
 }
 
 // Singleton instance