After spending 10 hours ripping apart everything, confirming configuration, I noticed that when using the “Test Email Autoconfiguration…” (holding CTRL while right clicking on Outlook tray icon), that the e-mail clients had a skewed order for checking autodiscovery. ![]() I have numerous other Outlook 2016 clients configured and working (installed as older versions, but have been updated), so I used those to troubleshoot (same scenario, domain joined on internal LAN and external WAN).
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