Mails stuck in outbox of shared mailbox

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Pyro Phoenix

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Hello community!

I've got a strange problem at one of my customers: When sending mails via Outlook, the mail got stuck in outbox.

Setup:

- Office 365
- Windows 10, 1909
- Server 2016 Essentials (DC)
- Azure AD Connect (User Synch to 365)

Outlook is connecting to Online Exchange, AD Connect is just used for User / Password export to Office 365

The shared mailbox is given access to the users via delegation preferences in ECP ('send as' and 'full access').

The personal and shared mailboxes are manually added as separate exchange accounts in Outlook, because:

- New mails should be automatically sent from the current active mailbox - without manually switching it in the 'from' field first. (doesn't work with auto mapped mailboxes)
- Sent mails should be stored in the outbox of the corresponding mailbox (doesn't work with auto mapped mailboxes)
- Deleted mails should be stored in the trash of the corresponding mailbox (doesn't work with auto mapped mailboxes)

There is no "DelegateSentItemsStyle" registry entry set.


Symptoms I could observe:

- When sending the mail, the Outlook status bar won't change to "sending mail 1 of 1" - it is doing nothing.
- Status is just "Online" instead of "Online with Microsoft Exchange"

Workaround:

Deleting and creating a new Outlook profile will temporarily fix this issue - but it randomly keeps coming back after some time.


Can somebody help here in this case? I were also able to find a report with similar issues but no current solution: Mails stuck in Outbox --> client says 'Online' instead of Online with Microsoft Exchange (Office 365)

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