Test Outlook on the web first because the result will distinguish a Microsoft 365/account issue affecting both devices from a problem limited to Classic Outlook.
1. Test the mailbox in a browser
Open https://outlook.office.com, sign in with the affected work account, then try to:
- Open a recent message.
- Send a test message to yourself.
- Confirm whether it arrives.
Microsoft recommends this webmail check when Classic Outlook shows Disconnected despite a working internet connection.^1^
2. If Outlook on the web also fails
This indicates that troubleshooting only the Windows application is unlikely to resolve the issue.
Ask your Microsoft 365 administrator to:
- Open Microsoft 365 admin center → Health → Service health.
- Check Exchange Online for an active incident or advisory.
- Review Issues for your organization to act on.
- If Exchange Online is healthy, run Diag: Troubleshoot Email Delivery for your mailbox.
The service-health page shows active incidents and organization-specific issues; the delivery diagnostic requires an administrator account and is unavailable in some sovereign Microsoft 365 environments.^2^^3^
If no incident appears, the administrator should check the account’s license, sign-in status, mailbox health, and authentication policies, then open a Microsoft support request through the admin center if necessary.
3. If Outlook on the web works
The mailbox and server are operating, so address the local Outlook connection separately. Since restarting Outlook and Windows did not help, proceed with these different checks:
- In Classic Outlook, select Send/Receive → Work Offline.
- If the button is shaded, select it once to return online.
- The status bar should change from Working Offline or Disconnected to Connected.^1^
- Update Office:
- Select File → Office Account → Update Options → Update Now.
- Refresh the account sign-in:
- Select File → Office Account → Sign out.
- Sign in again using the affected work account.
- If the password was recently changed, enter the new password when prompted; Outlook must also be updated with that credential.^4^
- If it remains disconnected, create a clean Outlook profile:
- Close Outlook.
- Open Control Panel → Mail (Microsoft Outlook) → Show Profiles → Add.
- Add the work account.
- Select Always use this profile, choose the new profile, and open Outlook.
- Confirm that the status changes to Connected and new messages synchronize.
Outdated software and damaged Outlook profiles are documented common causes of Microsoft 365 Outlook connection failures.^5^
For the phone, remove and add the work account only if webmail works and reauthentication does not restore synchronization. If webmail fails, wait for the administrator’s service/account findings rather than reconfiguring both devices.
References
- Classic Outlook(#tab/classic-outlook)
- How to check Microsoft 365 service health
- Find and fix email delivery issues as a Microsoft 365 for business admin
- New Outlook(#tab/new-outlook)
- Fix Outlook connection problems for Microsoft 365 account