diff --git a/apps/web/app/api/google/linking/auth-url/route.ts b/apps/web/app/api/google/linking/auth-url/route.ts
index af22452591..71df65c785 100644
--- a/apps/web/app/api/google/linking/auth-url/route.ts
+++ b/apps/web/app/api/google/linking/auth-url/route.ts
@@ -16,6 +16,7 @@ const getAuthUrl = ({ userId }: { userId: string }) => {
   const url = googleAuth.generateAuthUrl({
     access_type: "offline",
     scope: [...new Set([...SCOPES, "openid", "email"])].join(" "),
+    prompt: "consent",
     state,
   });
 
diff --git a/apps/web/utils/gmail/permissions.ts b/apps/web/utils/gmail/permissions.ts
index 5ad6ccd510..b6e93a4eb8 100644
--- a/apps/web/utils/gmail/permissions.ts
+++ b/apps/web/utils/gmail/permissions.ts
@@ -81,10 +81,20 @@ export async function handleGmailPermissionsCheck({
   refreshToken: string | null | undefined;
   emailAccountId: string;
 }) {
-  const { hasAllPermissions, error, missingScopes } =
-    await checkGmailPermissions({ accessToken, emailAccountId });
+  const permissionsBeforeRefresh = await checkGmailPermissions({
+    accessToken,
+    emailAccountId,
+  });
 
-  if (error === "invalid_token") {
+  if (
+    permissionsBeforeRefresh.error &&
+    [
+      "invalid_token",
+      "invalid_grant",
+      "invalid_scope",
+      "access_denied",
+    ].includes(permissionsBeforeRefresh.error)
+  ) {
     // attempt to refresh the token one last time using only the refresh token
     if (refreshToken) {
       try {
@@ -97,39 +107,57 @@ export async function handleGmailPermissionsCheck({
         });
 
         // re-check permissions with the new access token
-        const newAccessToken = getAccessTokenFromClient(gmailClient);
-        return await checkGmailPermissions({
-          accessToken: newAccessToken,
+        const accessToken = getAccessTokenFromClient(gmailClient);
+        const permissionsAfterRefresh = await checkGmailPermissions({
+          accessToken,
           emailAccountId,
         });
+
+        if (
+          permissionsAfterRefresh.error &&
+          permissionsAfterRefresh.error === "invalid_grant"
+        ) {
+          logger.info("Cleaning up invalid Gmail tokens", { emailAccountId });
+          const emailAccount = await prisma.emailAccount.findUnique({
+            where: { id: emailAccountId },
+            select: { accountId: true },
+          });
+          if (!emailAccount)
+            return {
+              hasAllPermissions: false,
+              error: "Email account not found",
+            };
+
+          await prisma.account.update({
+            where: { id: emailAccount.accountId },
+            data: {
+              access_token: null,
+              refresh_token: null,
+              expires_at: null,
+            },
+          });
+
+          return {
+            hasAllPermissions: false,
+            error: "Gmail access expired. Please reconnect your account.",
+            missingScopes: permissionsBeforeRefresh.missingScopes,
+          };
+        }
+
+        return permissionsAfterRefresh;
       } catch (_) {
-        // getGmailClientWithRefresh, getAccessTokenFromClient will throw if access token is invalid
-        // Refresh failed, fall through to cleanup
+        return {
+          hasAllPermissions: false,
+          error: "Gmail access expired. Please reconnect your account.",
+          missingScopes: permissionsBeforeRefresh.missingScopes,
+        };
       }
+    } else {
+      logger.warn("Got no refresh token to attempt refresh", {
+        emailAccountId,
+      });
     }
-
-    // Clean up invalid Gmail tokens (either no refresh token or refresh failed)
-    logger.info("Cleaning up invalid Gmail tokens", { emailAccountId });
-    const emailAccount = await prisma.emailAccount.findUnique({
-      where: { id: emailAccountId },
-    });
-    if (!emailAccount)
-      return { hasAllPermissions: false, error: "Email account not found" };
-
-    await prisma.account.update({
-      where: { id: emailAccount.accountId },
-      data: {
-        access_token: null,
-        refresh_token: null,
-        expires_at: null,
-      },
-    });
-    return {
-      hasAllPermissions: false,
-      error: "Gmail access expired. Please reconnect your account.",
-      missingScopes,
-    };
   }
 
-  return { hasAllPermissions, error, missingScopes };
+  return permissionsBeforeRefresh;
 }