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Autodiscover
Autodiscover is important. To check autodiscover services you can hold down ctrl whilst right clicking on the Outlook icon in the system tray and choosing "Test E-mail configuration"
You can also check by surfing to https://tripany-ad.local/autodiscover/autodiscover.xml and seeing if you get a response.
You also need to make sure you have an SRV record set in your DNS.