I'm hoping that someone can help me on this. I've separated this question out from my previous one because first of all my IP address was in there and second of all the response that was made to it pointed me in a brand new direction. For some reason, I'm unable to get Outlook Anywhere working with our Outlook 2010 clients, but it works fine with Outlook 2013 and Outlook 2016 clients. I've run into a bit of a brick wall here trying to troubleshoot this issue. The system can configure the mail just fine, but for some reason it can't log into the server. However, running the Microsoft Connectivity Analyzer works (I've attached the report). Both Outlook Anywhere and Outlook Autodiscover work, but Outlook 2010 clients can't connect, or "Log In" to the server. When the outlook profile is set up, it gets all the way to the last step and then gives the message "The connection to the Microsoft Exchange is unavailable. Outlook must be online or connected to complete this action." Once you launch outlook it just says "Disconnected" -- no password prompt or any other thing indicating that it's confused, it's just disconnected. We run Exchange 2010 on the back end and the laptops work fine if connected to the VPN, there is something evading us and I don't know what it is.
So, what I've done to troubleshoot this problem is:
Set up Outlook locally and try and run it remotely
Attempted to set up outlook remotely
Run the connectivity analyzer and had it pass
Connected to the VPN when remote and the e-mail works
Tested the e-mail locally and it works
Tested remote connectivity with Outlook 2013 and Outlook 2016 and it works