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Recently had a few instances where clients running Outlook 2016 in cached mode (connected to O365 Exchange Online) appeared not to be getting any updates to their offline global address list.
Trying to manually download via the usual send/receive settings menu does not work (this is apparently by design in newer versions of Outlook), but you can force it to redownload by closing Outlook and then browsing to the following folder:
C:\Users\<username>\AppData\Local\Microsoft\Outlook\Offline Address Books
In there you should see – in theory only one – folder (named presumably after the GUID of the O365 tenant). Simply rename this folder to <name>.old and relaunch Outlook, it should then force it to start afresh – whether this resolves the updating problem I have yet to discover but does at least work as an interim solution if nothing else!
