It simply wasn’t being passed to Outlook clients. All my virtual directories and URLs were fine, and the OAB was being generated fine without any issues. I spent 3 hours trying to find out why this was happening (I assumed it was configuration and/or IIS authentication related). Also when using the “Test EMail AutoConfiguration.” (by holding CTRL and right click on Outlook System Tray icon) to examine the AutoDiscover information, there was no OAB URL (OABUrl in XML) being sent to the clients.
When trying to perform a manual download (Send and Receive -> Download Address Book), it wasn’t in the list. After doing a migration from Microsoft Exchange 2013 to Exchange 2016 I noticed that my Offline Address Book (OAB) wasn’t being made available to Outlook clients.
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