Mixed-Network Troubleshooting Checklist

The old MacWindows archive was valuable because it collected small, concrete reports: a specific Mac model, a specific OS version, a specific Windows Server release, and a specific failure. This checklist keeps that spirit for modern support work.

Start with the exact environment

• Mac model, processor family, macOS version, and whether the Mac is managed.
• Windows Server version, domain functional level, file server role, and Exchange version if email is involved.
• Network path: office LAN, Wi-Fi, VPN, remote user, or split DNS environment.
• Protocol: SMB, AFP, DFS, WebDAV, LPR, IPP, Exchange, IMAP, or RDP.

Then test in order

1. DNS and time sync.
2. Directory login or local account behavior.
3. Kerberos ticket or password authentication.
4. Direct server access by hostname and by IP address.
5. File open, save, rename, delete, and search.
6. Printing a plain PDF.
7. Email Autodiscover, certificate trust, and calendar sync.
8. VPN and remote access behavior outside the office.

This sequence prevents a common mistake: debugging the application first when the actual failure is DNS, credentials, or a stale cached connection.