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This blog is split in two parts, first covering checkpoints for a correct setup for GAL pictures and the second Outlook client troubeshooting focused on Exchange Cached Mode.
Once your shared mailbox account is ready (created either on Active Directory on-premises or on Azure Active Directory) you can proceed by adding it to your Outlook profile. Once configured, the shared mailbox will be automatically available in the left folder pane in Outlook. Select the permission level—Editor permissions will provide full access—and click OK. Open Outlook again and reconnect the shared mailbox following the process listed for step number 1 (How to add an additional shared mailbox on Outlook). Office 365 keeps your mailboxes (shared or individual) on a server called Microsoft Exchange.
You should keep in mind, however, that there are different methods to do this. With the exception of the mailbox owner, anyone else who needs to access the additional mailbox (and configure it on his Outlook profile) must be granted the correct permissions. Shared mailboxes might suffer from a wide range of technical and configuration issues. However, Outlook locally caches all folders to which you have access (also for shared mailboxes) in a file called Offline Outlook Data File (.ost).
Outlook should create a new Offline Outlook Data File, which will start to synchronize again with the Mailbox on the Exchange Server.
This allows us to access e-mail, calendars, contacts, tasks, and other mailbox content when something is wrong with Outlook.
Just go to https://login.microsoftonline.com, provide your credentials (Outlook email address and password) and log in. If the Mailbox is available and properly synchronizing via Outlook Web App, this means that the issue is local, with Microsoft Outlook, and you will need to investigate further.
Using Cached Exchange Mode, you can read and respond to your cached messages while offline, and any new messages or updates to your mailbox on the server will be automatically sent/received once Outlook (specifically the file) gets connected again.
If the shared mailbox is not synchronizing, you might try to disable, restart Outlook, and re-enable again Cached Exchange Mode on the advanced profile configuration settings of your Outlook profile. Highlight the Exchange account, and then click Change. On the Advanced tab, under Cached Exchange Mode Settings, uncheck the option Cached Exchange Mode. The Autodiscover service should be able to create the Outlook profile automatically: Click on Next. Go again to the Mail Configuration window and select the option: ”Always use this profile”. Next time Outlook opens up, it will automatically load your new profile.