Exchange server 2013 / Outlook 2013

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Outlook version
Outlook 2013 64 bit
Email Account
Exchange Server
I hope I am posting this in the right area since it may fall into either Outlook or Exchange.

We have a group of roughly 30 employees who use our Terminal Server for work. Each user uses Outlook 2013 for email and we have set them up on our Exchange server (2013). This is where the issues seem to happen for them. Emails will constantly get stuck in their outbox and never get sent out. Other issues arise in that some cases the signature does not populate when replying to a external email (, One of the bigger issues is that for no reason Outlook will want them to constantly type in their user name / password and the box will show up at random. These are just a few of the situations that seem to be happening and I have just recently took over the IT admin role and with little experience in dealing with Exchange Server, I am quickly drowning with these issues.

On a side note, which makes me believe its a communication or compatibility issue is that those who do not use Terminal to work in have no issues sending or receiving emails using Outlook and the exchange server at all.
There are issues with terminal server environments, always have been. Are the profiles using cached mode or online? Online generally works better than cached mode. That should fix the email not sending problem but not the signatures and probably not the password dialog.
Hi Diane,

Thanks for the quick reply and providing me with some piece of mind. I was kind of leaning towards compatibility issues and will bring this up to those powers that be. As for cached mode, I will double check all the users settings and see how outlook has been set up. I will report back in a few days and see if anyone else has suggestions.
If they are in cached mode, set up one in online mode to test - see if it works better.
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