Outlook 2013 / Exchange 2013 : Shared mailboxes - Mail stuck in outbox (non-cached), Mail sends but doesn't get received (cached).

Hello,
We are currently experiencing some weird behaviour in Outlook 2013 since we added Shared Mailboxes.
When we run Outlook 2013 with cached mode
enabled:
- I create a new e-mail and send it.
- The e-mail goes to the outbox, and get's 'send'.
- None of the recipients receives the e-mail.
When we run Outlook 2013 with cached mode
disabled:
- I create a new e-mail and send it.
- The e-mail goes to the outbox, but remains there.
Now to make things even more bizarre:
When I switch from 'cached'-mode to 'non cached'-mode, I see all the e-mail that were 'send' in cached-mode stuck in the outbox.
Note: The DNS server configuration in Exchange is correct.

Hi,
How about sending on OWA? Does the issue exist?
To troubleshoot the issue, let's run Outlook in Safe Mode to determine if 3rd-party add-ins are related:
Press Win + R and type “outlook.exe /safe” in the blank box, then press Enter.
If there’s no problem sending emails in Safe Mode, disable the suspicious add-ins to verify which add-ins caused this issue.
Please also disable the firewall and anti-virus program to send the emails again, in many scenarios the protection may cause the issue.
Please also keep Exchange and Outlook patched to the latest.
Regards,
Melon Chen
TechNet Community Support

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