Offline address book not updating automatically
When you have Cached Exchange Mode enabled, Outlook by will by default cache the main Global Address List as well.
This is called the Offline Address Book and is being generated on the Exchange server.
Use Cached Exchange Mode but without OABTo always work with the Online Address Book, even when you have Cached Exchange Mode enabled, you can set the following Registry key and value.
Key: All Users or any other object type such as All Contacts, All Groups or All Rooms.
OAB Update schedule To change the OAB Update Schedule via the Exchange Management Console: Organization Configuration-Rather than changing the default schedule, you can also force an update and redistribution of the Offline Address Book.
This is great for testing or when it is important that changes are published immediately (note that users must still update the OAB manually or wait a OAB sync interval to see the changes).
This means that in the worst possible scenario, an update to the Address Book won’t become available to the user until 48 hours after the change.
This situation however is extremely rare since the default maintenance time on Exchange is at AM and updates and downloads are usually performed during working hours.
I disable cache mode and it works fine but I don't want to keep it disabled, I also tried by delete the OAB file in C:\Users\username\App Data\Local\Microsoft\Outlook\Offline Address Books and download OAB manually rather then waiting for 24 hours, it's still same.
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Renaming just a single or some of the files will result in an OAB corruption. A benefit of manually deleting the oab-file is that before they are being re-downloaded, you are working with the Online Address Book.
When you find things working correctly for you now but not anymore after the oab-file were redownloaded, you know that the issue is with the oab-files on the server and not on the client or the Address Book configuration in general.