fix(token-refresh): microsoft, notion, x, linear (#2933)

* fix(microsoft): proactive refresh needed

* fix(x): missing token refresh flag

* notion and linear missing flag too

* address bugbot comment

Author: icecrasher321

apps/sim/app/api/auth/oauth/utils.ts

@@ -4,6 +4,11 @@ import { createLogger } from '@sim/logger'
 import { and, desc, eq, inArray } from 'drizzle-orm'
 import { getSession } from '@/lib/auth'
 import { refreshOAuthToken } from '@/lib/oauth'
+import {
+  getMicrosoftRefreshTokenExpiry,
+  isMicrosoftProvider,
+  PROACTIVE_REFRESH_THRESHOLD_DAYS,
+} from '@/lib/oauth/microsoft'
 
 const logger = createLogger('OAuthUtilsAPI')
 
@@ -205,15 +210,32 @@ export async function refreshAccessTokenIfNeeded(
   }
 
   // Decide if we should refresh: token missing OR expired
-  const expiresAt = credential.accessTokenExpiresAt
+  const accessTokenExpiresAt = credential.accessTokenExpiresAt
+  const refreshTokenExpiresAt = credential.refreshTokenExpiresAt
   const now = new Date()
-  const shouldRefresh =
-    !!credential.refreshToken && (!credential.accessToken || (expiresAt && expiresAt <= now))
+
+  // Check if access token needs refresh (missing or expired)
+  const accessTokenNeedsRefresh =
+    !!credential.refreshToken &&
+    (!credential.accessToken || (accessTokenExpiresAt && accessTokenExpiresAt <= now))
+
+  // Check if we should proactively refresh to prevent refresh token expiry
+  // This applies to Microsoft providers whose refresh tokens expire after 90 days of inactivity
+  const proactiveRefreshThreshold = new Date(
+    now.getTime() + PROACTIVE_REFRESH_THRESHOLD_DAYS * 24 * 60 * 60 * 1000
+  )
+  const refreshTokenNeedsProactiveRefresh =
+    !!credential.refreshToken &&
+    isMicrosoftProvider(credential.providerId) &&
+    refreshTokenExpiresAt &&
+    refreshTokenExpiresAt <= proactiveRefreshThreshold
+
+  const shouldRefresh = accessTokenNeedsRefresh || refreshTokenNeedsProactiveRefresh
 
   const accessToken = credential.accessToken
 
   if (shouldRefresh) {
-    logger.info(`[${requestId}] Token expired, attempting to refresh for credential`)
+    logger.info(`[${requestId}] Refreshing token for credential`)
     try {
       const refreshedToken = await refreshOAuthToken(
         credential.providerId,
@@ -227,11 +249,15 @@ export async function refreshAccessTokenIfNeeded(
           userId: credential.userId,
           hasRefreshToken: !!credential.refreshToken,
         })
+        if (!accessTokenNeedsRefresh && accessToken) {
+          logger.info(`[${requestId}] Proactive refresh failed but access token still valid`)
+          return accessToken
+        }
         return null
       }
 
       // Prepare update data
-      const updateData: any = {
+      const updateData: Record<string, unknown> = {
         accessToken: refreshedToken.accessToken,
         accessTokenExpiresAt: new Date(Date.now() + refreshedToken.expiresIn * 1000),
         updatedAt: new Date(),
@@ -243,6 +269,10 @@ export async function refreshAccessTokenIfNeeded(
         updateData.refreshToken = refreshedToken.refreshToken
       }
 
+      if (isMicrosoftProvider(credential.providerId)) {
+        updateData.refreshTokenExpiresAt = getMicrosoftRefreshTokenExpiry()
+      }
+
       // Update the token in the database
       await db.update(account).set(updateData).where(eq(account.id, credentialId))
 
@@ -256,6 +286,10 @@ export async function refreshAccessTokenIfNeeded(
         credentialId,
         userId: credential.userId,
       })
+      if (!accessTokenNeedsRefresh && accessToken) {
+        logger.info(`[${requestId}] Proactive refresh failed but access token still valid`)
+        return accessToken
+      }
       return null
     }
   } else if (!accessToken) {
@@ -277,10 +311,27 @@ export async function refreshTokenIfNeeded(
   credentialId: string
 ): Promise<{ accessToken: string; refreshed: boolean }> {
   // Decide if we should refresh: token missing OR expired
-  const expiresAt = credential.accessTokenExpiresAt
+  const accessTokenExpiresAt = credential.accessTokenExpiresAt
+  const refreshTokenExpiresAt = credential.refreshTokenExpiresAt
   const now = new Date()
-  const shouldRefresh =
-    !!credential.refreshToken && (!credential.accessToken || (expiresAt && expiresAt <= now))
+
+  // Check if access token needs refresh (missing or expired)
+  const accessTokenNeedsRefresh =
+    !!credential.refreshToken &&
+    (!credential.accessToken || (accessTokenExpiresAt && accessTokenExpiresAt <= now))
+
+  // Check if we should proactively refresh to prevent refresh token expiry
+  // This applies to Microsoft providers whose refresh tokens expire after 90 days of inactivity
+  const proactiveRefreshThreshold = new Date(
+    now.getTime() + PROACTIVE_REFRESH_THRESHOLD_DAYS * 24 * 60 * 60 * 1000
+  )
+  const refreshTokenNeedsProactiveRefresh =
+    !!credential.refreshToken &&
+    isMicrosoftProvider(credential.providerId) &&
+    refreshTokenExpiresAt &&
+    refreshTokenExpiresAt <= proactiveRefreshThreshold
+
+  const shouldRefresh = accessTokenNeedsRefresh || refreshTokenNeedsProactiveRefresh
 
   // If token appears valid and present, return it directly
   if (!shouldRefresh) {
@@ -293,13 +344,17 @@ export async function refreshTokenIfNeeded(
 
     if (!refreshResult) {
       logger.error(`[${requestId}] Failed to refresh token for credential`)
+      if (!accessTokenNeedsRefresh && credential.accessToken) {
+        logger.info(`[${requestId}] Proactive refresh failed but access token still valid`)
+        return { accessToken: credential.accessToken, refreshed: false }
+      }
       throw new Error('Failed to refresh token')
     }
 
     const { accessToken: refreshedToken, expiresIn, refreshToken: newRefreshToken } = refreshResult
 
     // Prepare update data
-    const updateData: any = {
+    const updateData: Record<string, unknown> = {
       accessToken: refreshedToken,
       accessTokenExpiresAt: new Date(Date.now() + expiresIn * 1000), // Use provider's expiry
       updatedAt: new Date(),
@@ -311,6 +366,10 @@ export async function refreshTokenIfNeeded(
       updateData.refreshToken = newRefreshToken
     }
 
+    if (isMicrosoftProvider(credential.providerId)) {
+      updateData.refreshTokenExpiresAt = getMicrosoftRefreshTokenExpiry()
+    }
+
     await db.update(account).set(updateData).where(eq(account.id, credentialId))
 
     logger.info(`[${requestId}] Successfully refreshed access token`)
@@ -331,6 +390,11 @@ export async function refreshTokenIfNeeded(
       }
     }
 
+    if (!accessTokenNeedsRefresh && credential.accessToken) {
+      logger.info(`[${requestId}] Proactive refresh failed but access token still valid`)
+      return { accessToken: credential.accessToken, refreshed: false }
+    }
+
     logger.error(`[${requestId}] Refresh failed and no valid token found in DB`, error)
     throw error
   }

apps/sim/lib/auth/auth.ts

@@ -64,6 +64,8 @@ import { SSO_TRUSTED_PROVIDERS } from './sso/constants'
 
 const logger = createLogger('Auth')
 
+import { getMicrosoftRefreshTokenExpiry, isMicrosoftProvider } from '@/lib/oauth/microsoft'
+
 const validStripeKey = env.STRIPE_SECRET_KEY
 
 let stripeClient = null
@@ -187,6 +189,10 @@ export const auth = betterAuth({
               }
             }
 
+            const refreshTokenExpiresAt = isMicrosoftProvider(account.providerId)
+              ? getMicrosoftRefreshTokenExpiry()
+              : account.refreshTokenExpiresAt
+
             await db
               .update(schema.account)
               .set({
@@ -195,7 +201,7 @@ export const auth = betterAuth({
                 refreshToken: account.refreshToken,
                 idToken: account.idToken,
                 accessTokenExpiresAt: account.accessTokenExpiresAt,
-                refreshTokenExpiresAt: account.refreshTokenExpiresAt,
+                refreshTokenExpiresAt,
                 scope: scopeToStore,
                 updatedAt: new Date(),
               })
@@ -292,6 +298,13 @@ export const auth = betterAuth({
             }
           }
 
+          if (isMicrosoftProvider(account.providerId)) {
+            await db
+              .update(schema.account)
+              .set({ refreshTokenExpiresAt: getMicrosoftRefreshTokenExpiry() })
+              .where(eq(schema.account.id, account.id))
+          }
+
           // Sync webhooks for credential sets after connecting a new credential
           const requestId = crypto.randomUUID().slice(0, 8)
           const userMemberships = await db

apps/sim/lib/oauth/index.ts

@@ -1,3 +1,4 @@
+export * from './microsoft'
 export * from './oauth'
 export * from './types'
 export * from './utils'

apps/sim/lib/oauth/microsoft.ts

@@ -0,0 +1,19 @@
+export const MICROSOFT_REFRESH_TOKEN_LIFETIME_DAYS = 90
+export const PROACTIVE_REFRESH_THRESHOLD_DAYS = 7
+
+export const MICROSOFT_PROVIDERS = new Set([
+  'microsoft-excel',
+  'microsoft-planner',
+  'microsoft-teams',
+  'outlook',
+  'onedrive',
+  'sharepoint',
+])
+
+export function isMicrosoftProvider(providerId: string): boolean {
+  return MICROSOFT_PROVIDERS.has(providerId)
+}
+
+export function getMicrosoftRefreshTokenExpiry(): Date {
+  return new Date(Date.now() + MICROSOFT_REFRESH_TOKEN_LIFETIME_DAYS * 24 * 60 * 60 * 1000)
+}

apps/sim/lib/oauth/oauth.ts

@@ -835,6 +835,7 @@ function getProviderAuthConfig(provider: string): ProviderAuthConfig {
         clientId,
         clientSecret,
         useBasicAuth: true,
+        supportsRefreshTokenRotation: true,
       }
     }
     case 'confluence': {
@@ -883,6 +884,7 @@ function getProviderAuthConfig(provider: string): ProviderAuthConfig {
         clientId,
         clientSecret,
         useBasicAuth: false,
+        supportsRefreshTokenRotation: true,
       }
     }
     case 'microsoft':
@@ -910,6 +912,7 @@ function getProviderAuthConfig(provider: string): ProviderAuthConfig {
         clientId,
         clientSecret,
         useBasicAuth: true,
+        supportsRefreshTokenRotation: true,
       }
     }
     case 'dropbox': {