Unable to send email from Mac using Outlook for Mac 2011

I have a single user that cannot send email from the Mac after migrating to Exchange 2013 on-prem. I myself am on the same Exchange server and am using a Mac with Office 2011 and am able to send/receive emails without any issues.
When the user sends an email it goes to the sent mail folder and syncs with the server and can be seen on a windows machine running any other version of Office (same in OWA). I've logged the user in on my Mac and blown away my profile and seeing the same issue.
Not sure if this narrows my issue down to the Exchange server receiving the send request from a Mac or if it's some setting in Outlook on the Mac?
I do not see anything in the logs on the server and have not seen any error son the Mac.
Any thoughts as to where my issues is?

Hi,
According to your description, I find that there is a single user cannot send email.
I suggest using Outlook on Windows machine and sending emails via this single user to verify whether the emails can be sent.
If the single user can send email via Outlook on Windows machine, it seems an issue on the Mac side.
I suggest asking Outlook for Mac Forum for help so that we can get more professional suggestions.
For your convenience:
http://answers.microsoft.com/en-us/mac/forum/macoutlook?tab=Threads
If can't send emails in Outlook, it seems an issue on the single user side.
I suggest trying to access the single user's mailbox via OWA to verify whether the mailbox has been migrated completely.
Thanks
Mavis
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