Outlook does not use OS X Directory Services stack Im referring to the Outlook setting located here Outlook I have seen that MS Tech Net document, thank you @jonnydford. I'm using Office 365, so I can only show you what I get from that (below).It covers only Outlook 2011 (which may have the same behavior as Outlook 2016, but the data caches certainly live in different locations) I tried to flush caches what I think is the correct location for Outlook 2016: ~/Library/Containers/com.microsoft. Outlook/ However, Im not sure if this where the GAL directory settings live. I expect it's a bit more understandable with an on-prem Exchange server.The key at the end of the URL ("2d1f6b5f-c74d-4803-b7f4-fbbda4ee8c30"), do you know if that key exists in your "UBF8T346G9. Older versions had an issue where the Keychain entries were causing problems prompting users to log in at every launch.Office" location that might be able to be passed to the "gal download directory"? @pbowden with Microsoft created a tool to deal with this.Here is a run down on what the (2) MS engineers told me: -Don't change anything manually.-Outlook will dynamically pick up the new AD/Exchange infrastructure changes. They actually escalated the ticket twice, thus I got fairly high up in rank I think. We recently shut down the legacy DCs I mentioned in my original post, and brought the new DCs online as planned. We did it nice 'n slow to make sure the new servers were functioning before we yanked the old servers. However, when we manually add our Exchange Accounts in Outlook, the GAL and OAB work perfectly. However, when turning on Auto Discover, we are finding that users are being prompted with a log in message box every time the close and open Outlook.
In order to reflect any changes or updates made to the Global Address List, you can force Outlook to download a new copy of the GAL.
I assume it does this by searching for _ldap._loc SVR records in DNS or it does it via AD CAS Auto Discover foo that Im unaware of. Through this post, I found what looks to be the Offline Address Book .plist file here: /Users/isaachalvorson/Library/Group Containers/UBF8T346G9.
Im concerned that once my old DCs are phased-out that my Outlook users will no longer be able to do GAL lookups from AD because Outlook will be pointing to stale/deprecated servers. Office/Outlook/Outlook 15 Profiles/Main Profile/Caches/1 I tried quitting Outlook, and deleting the OABQuery Info.plist file as advised in that article.
When connected to an Exchange server, Outlook will automatically synchronize the address book once every 24 hours.
However, if you need to the address book to update sooner you will need to force an update by manually starting the synchronization process.
After completing this tutorial you will have configured Microsoft Outlook to always reference the latest version of the global address book directly from the email server rather than referencing a downloaded local copy. After following these steps, you will only be able to access the global address book while Outlook is connected to the server.