diff --git a/apps/sim/contexts/socket-context.test.tsx b/apps/sim/contexts/socket-context.test.tsx
new file mode 100644
index 000000000..5f1c8df74
--- /dev/null
+++ b/apps/sim/contexts/socket-context.test.tsx
@@ -0,0 +1,278 @@
+/**
+ * @vitest-environment jsdom
+ */
+
+import { act, renderHook, waitFor } from '@testing-library/react'
+import { io } from 'socket.io-client'
+import { afterEach, beforeEach, describe, expect, it, vi } from 'vitest'
+import { SocketProvider, useSocket } from './socket-context'
+
+vi.mock('socket.io-client')
+const mockIo = vi.mocked(io)
+
+global.fetch = vi.fn()
+const mockFetch = vi.mocked(fetch)
+
+vi.mock('@/lib/logs/console-logger', () => ({
+  createLogger: () => ({
+    info: vi.fn(),
+    error: vi.fn(),
+    warn: vi.fn(),
+    debug: vi.fn(),
+  }),
+}))
+
+describe('SocketContext Token Refresh', () => {
+  let mockSocket: any
+  let eventHandlers: Record<string, any>
+
+  beforeEach(() => {
+    eventHandlers = {}
+    mockSocket = {
+      id: 'test-socket-id',
+      connected: true,
+      io: { engine: { transport: { name: 'websocket' } } },
+      auth: { token: 'initial-token' },
+      on: vi.fn((event, handler) => {
+        eventHandlers[event] = handler
+      }),
+      connect: vi.fn(),
+      disconnect: vi.fn(),
+      emit: vi.fn(),
+      close: vi.fn(),
+    }
+
+    mockIo.mockReturnValue(mockSocket)
+
+    mockFetch.mockResolvedValue({
+      ok: true,
+      json: async () => ({ token: 'fresh-token' }),
+    } as Response)
+  })
+
+  afterEach(() => {
+    vi.clearAllMocks()
+  })
+
+  const renderSocketProvider = async (user = { id: 'test-user', name: 'Test User' }) => {
+    const result = renderHook(() => useSocket(), {
+      wrapper: ({ children }) => <SocketProvider user={user}>{children}</SocketProvider>,
+    })
+
+    await waitFor(() => {
+      expect(mockSocket.on).toHaveBeenCalledWith('connect_error', expect.any(Function))
+    })
+
+    vi.clearAllMocks()
+
+    mockFetch.mockResolvedValue({
+      ok: true,
+      json: async () => ({ token: 'fresh-token' }),
+    } as Response)
+
+    return result
+  }
+
+  describe('Token Refresh on Connection Error', () => {
+    it('should refresh token on authentication failure', async () => {
+      const { result } = await renderSocketProvider()
+
+      const error = { message: 'Token validation failed' }
+
+      await act(async () => {
+        await eventHandlers.connect_error(error)
+      })
+
+      expect(mockFetch).toHaveBeenCalledWith('/api/auth/socket-token', {
+        method: 'POST',
+        credentials: 'include',
+      })
+
+      // Should update socket auth and reconnect
+      expect(mockSocket.auth.token).toBe('fresh-token')
+      expect(mockSocket.connect).toHaveBeenCalled()
+    })
+
+    it('should limit token refresh attempts to 3', async () => {
+      const { result } = await renderSocketProvider()
+
+      const error = { message: 'Token validation failed' }
+
+      for (let i = 0; i < 4; i++) {
+        await act(async () => {
+          await eventHandlers.connect_error(error)
+        })
+      }
+
+      // Should only call fetch 3 times (max attempts)
+      expect(mockFetch).toHaveBeenCalledTimes(3)
+      expect(mockSocket.connect).toHaveBeenCalledTimes(3)
+    })
+
+    it('should prevent concurrent token refresh attempts', async () => {
+      const { result } = await renderSocketProvider()
+
+      let resolveTokenFetch!: (value: {
+        ok: boolean
+        json: () => Promise<{ token: string }>
+      }) => void
+      const slowTokenPromise = new Promise((resolve) => {
+        resolveTokenFetch = resolve
+      })
+
+      mockFetch.mockReturnValue(slowTokenPromise as any)
+
+      const error = { message: 'Authentication failed' }
+
+      // Start two concurrent refresh attempts
+      const promise1 = act(async () => {
+        await eventHandlers.connect_error(error)
+      })
+
+      const promise2 = act(async () => {
+        await eventHandlers.connect_error(error)
+      })
+
+      // Resolve the slow fetch
+      resolveTokenFetch({
+        ok: true,
+        json: async () => ({ token: 'fresh-token' }),
+      })
+
+      await Promise.all([promise1, promise2])
+
+      // Should only call fetch once (concurrent protection)
+      expect(mockFetch).toHaveBeenCalledTimes(1)
+    })
+
+    it('should reset retry counter on successful connection', async () => {
+      const { result } = await renderSocketProvider()
+
+      const error = { message: 'Token validation failed' }
+
+      // Use up 2 retry attempts
+      await act(async () => {
+        await eventHandlers.connect_error(error)
+      })
+      await act(async () => {
+        await eventHandlers.connect_error(error)
+      })
+
+      expect(mockFetch).toHaveBeenCalledTimes(2)
+
+      // Simulate successful connection (resets counter)
+      await act(async () => {
+        eventHandlers.connect()
+      })
+
+      // Should be able to retry again (counter reset)
+      await act(async () => {
+        await eventHandlers.connect_error(error)
+      })
+
+      expect(mockFetch).toHaveBeenCalledTimes(3)
+    })
+
+    it('should handle token refresh failure gracefully', async () => {
+      const { result } = await renderSocketProvider()
+
+      // Mock failed token refresh after initialization
+      mockFetch.mockResolvedValue({
+        ok: false,
+        status: 401,
+      } as Response)
+
+      const error = { message: 'Token validation failed' }
+
+      await act(async () => {
+        await eventHandlers.connect_error(error)
+      })
+
+      // Should attempt refresh but not update auth or reconnect
+      expect(mockFetch).toHaveBeenCalled()
+      expect(mockSocket.auth.token).toBe('initial-token') // unchanged
+      expect(mockSocket.connect).not.toHaveBeenCalled()
+    })
+
+    it('should handle fetch errors gracefully', async () => {
+      const { result } = await renderSocketProvider()
+
+      // Mock fetch error after initialization
+      mockFetch.mockRejectedValue(new Error('Network error'))
+
+      const error = { message: 'Authentication failed' }
+
+      // Should not throw error
+      await act(async () => {
+        await eventHandlers.connect_error(error)
+      })
+
+      expect(mockFetch).toHaveBeenCalled()
+      expect(mockSocket.connect).not.toHaveBeenCalled()
+    })
+
+    it('should only refresh token on authentication-related errors', async () => {
+      const { result } = await renderSocketProvider()
+
+      // Non-authentication error
+      const networkError = { message: 'Network timeout' }
+
+      await act(async () => {
+        await eventHandlers.connect_error(networkError)
+      })
+
+      // Should not attempt token refresh
+      expect(mockFetch).not.toHaveBeenCalled()
+      expect(mockSocket.connect).not.toHaveBeenCalled()
+    })
+  })
+
+  describe('Interaction with Socket.IO Reconnection', () => {
+    it('should work with Socket.IO built-in reconnection attempts', async () => {
+      const { result } = await renderSocketProvider()
+
+      // Simulate Socket.IO reconnection cycle
+      await act(async () => {
+        // Reconnection attempt starts
+        eventHandlers.reconnect_attempt(1)
+      })
+
+      await act(async () => {
+        // Fails with auth error
+        await eventHandlers.connect_error({ message: 'Token validation failed' })
+      })
+
+      // Should refresh token and attempt reconnection
+      expect(mockFetch).toHaveBeenCalled()
+      expect(mockSocket.connect).toHaveBeenCalled()
+    })
+
+    it('should reset counters on successful reconnect', async () => {
+      const { result } = await renderSocketProvider()
+
+      // Use up retry attempts
+      const error = { message: 'Authentication failed' }
+      await act(async () => {
+        await eventHandlers.connect_error(error)
+      })
+
+      await act(async () => {
+        await eventHandlers.connect_error(error)
+      })
+
+      expect(mockFetch).toHaveBeenCalledTimes(2)
+
+      // Simulate successful reconnection
+      await act(async () => {
+        eventHandlers.reconnect(1)
+      })
+
+      // Should reset and allow new attempts
+      await act(async () => {
+        await eventHandlers.connect_error(error)
+      })
+
+      expect(mockFetch).toHaveBeenCalledTimes(3)
+    })
+  })
+})
diff --git a/apps/sim/contexts/socket-context.tsx b/apps/sim/contexts/socket-context.tsx
index a8045e196..cccb7c20f 100644
--- a/apps/sim/contexts/socket-context.tsx
+++ b/apps/sim/contexts/socket-context.tsx
@@ -87,6 +87,8 @@ export function SocketProvider({ children, user }: SocketProviderProps) {
 
   // Connection state tracking
   const reconnectCount = useRef(0)
+  const tokenRefreshAttempts = useRef(0)
+  const isRefreshingToken = useRef(false)
 
   // Use refs to store event handlers to avoid stale closures
   const eventHandlers = useRef<{
@@ -138,7 +140,9 @@ export function SocketProvider({ children, user }: SocketProviderProps) {
         const socketInstance = io(socketUrl, {
           transports: ['websocket', 'polling'], // Keep polling fallback for reliability
           withCredentials: true,
-          reconnectionAttempts: 5, // Back to original conservative setting
+          reconnectionAttempts: 5, // Socket.IO handles base reconnection
+          reconnectionDelay: 1000, // Start with 1 second delay
+          reconnectionDelayMax: 5000, // Max 5 second delay
           timeout: 10000, // Back to original timeout
           auth: {
             token, // Send one-time token for authentication
@@ -150,6 +154,7 @@ export function SocketProvider({ children, user }: SocketProviderProps) {
           setIsConnected(true)
           setIsConnecting(false)
           reconnectCount.current = 0
+          tokenRefreshAttempts.current = 0
 
           logger.info('Socket connected successfully', {
             socketId: socketInstance.id,
@@ -172,7 +177,7 @@ export function SocketProvider({ children, user }: SocketProviderProps) {
           setPresenceUsers([])
         })
 
-        socketInstance.on('connect_error', (error: any) => {
+        socketInstance.on('connect_error', async (error: any) => {
           setIsConnecting(false)
           logger.error('Socket connection error:', {
             message: error.message,
@@ -181,11 +186,54 @@ export function SocketProvider({ children, user }: SocketProviderProps) {
             type: error.type,
             transport: error.transport,
           })
+
+          if (
+            error.message?.includes('Token validation failed') ||
+            error.message?.includes('Authentication failed')
+          ) {
+            // Prevent infinite loops - limit refresh attempts
+            if (tokenRefreshAttempts.current >= 3) {
+              logger.warn('Max token refresh attempts reached - user needs to refresh page')
+              return
+            }
+
+            // Prevent concurrent refresh attempts
+            if (isRefreshingToken.current) {
+              logger.info('Token refresh already in progress, skipping...')
+              return
+            }
+
+            isRefreshingToken.current = true
+            tokenRefreshAttempts.current++
+            logger.info(`Token expired, attempting refresh (${tokenRefreshAttempts.current}/3)...`)
+
+            try {
+              const tokenResponse = await fetch('/api/auth/socket-token', {
+                method: 'POST',
+                credentials: 'include',
+              })
+
+              if (tokenResponse.ok) {
+                const { token } = await tokenResponse.json()
+                socketInstance.auth = { ...socketInstance.auth, token }
+                logger.info('Token refreshed successfully, reconnecting...')
+                socketInstance.connect()
+              } else {
+                logger.warn('Failed to refresh token - user may need to refresh page')
+              }
+            } catch (refreshError) {
+              logger.error('Token refresh failed:', refreshError)
+            } finally {
+              isRefreshingToken.current = false
+            }
+          }
         })
 
         // Add reconnection logging
         socketInstance.on('reconnect', (attemptNumber) => {
           reconnectCount.current = attemptNumber
+          // Reset token refresh attempts on successful reconnection
+          tokenRefreshAttempts.current = 0
           logger.info('Socket reconnected', {
             attemptNumber,
           })
diff --git a/apps/sim/lib/auth.ts b/apps/sim/lib/auth.ts
index 68a3125ce..8608da260 100644
--- a/apps/sim/lib/auth.ts
+++ b/apps/sim/lib/auth.ts
@@ -187,7 +187,7 @@ export const auth = betterAuth({
   plugins: [
     nextCookies(),
     oneTimeToken({
-      expiresIn: 10, // 10 minutes - enough time for socket connection
+      expiresIn: 30, // 30 minutes - covers typical work sessions
     }),
     emailOTP({
       sendVerificationOTP: async (data: {
diff --git a/apps/sim/socket-server/config/socket.ts b/apps/sim/socket-server/config/socket.ts
index 0ec9f3261..681c3fda9 100644
--- a/apps/sim/socket-server/config/socket.ts
+++ b/apps/sim/socket-server/config/socket.ts
@@ -36,7 +36,7 @@ export function createSocketIOServer(httpServer: HttpServer): Server {
       allowedHeaders: ['Content-Type', 'Authorization', 'Cookie', 'socket.io'],
       credentials: true, // Enable credentials to accept cookies
     },
-    transports: ['polling', 'websocket'], // Keep both transports for reliability
+    transports: ['websocket', 'polling'], // WebSocket first, polling as fallback
     allowEIO3: true, // Keep legacy support for compatibility
     pingTimeout: 60000, // Back to original conservative setting
     pingInterval: 25000, // Back to original interval
@@ -52,7 +52,7 @@ export function createSocketIOServer(httpServer: HttpServer): Server {
 
   logger.info('Socket.IO server configured with:', {
     allowedOrigins: allowedOrigins.length,
-    transports: ['polling', 'websocket'],
+    transports: ['websocket', 'polling'],
     pingTimeout: 60000,
     pingInterval: 25000,
     maxHttpBufferSize: 1e6,