Hello,

I am running into an issue using Lync for Mac where I can connect to Lync and make calls but I am unable to make calls to our internal organization's conference bridge (hyperlinks and dialing the bridge both do not work).  This issue only occurs when I am using our new fully-routed VPN solution.  However, there are a number of "strange" factors related to that statement that make me feel like it has something to do with settings on the Mac or the Lync for Mac client itself and not a network issue (will explain in my details below).

Some background information so you can hopefully help me troubleshoot my issue a bit easier:

1. I am running into an issue on Lync for Mac (version 14.1.1 (150716)) and I am running OSX Yosemite 10.10.5. 

2. Lync for Mac works without issue when I am off-network or on-network (able to dial conference line like a champ).  However, I run into my issue when I use our company's new VPN solution that is fully routed.

3. When I am on our new VPN solution and I emulate a Windows VM on top of my Mac and run Lync there, I run into no issues and I can connect to conference lines without issue (this to me seems to rule out routing / network connectivity issues).

4. Our VPN solution is a new solution we are rolling out and I am one of several testers.  All but one of our testers on Mac are having the same issue I am with being unable to connect to our bridge line.  However, one of our Mac users that is running the same version of everything (and the same programs (AV / Firewalls / etc) can connect without issue.

I've run troubleshooting logs and I'll post them next for reference.  If anyone can help me figure this one out I would really appreciate it!

Thanks for your help,

Jeff

Not letting me post logs (too large).  Let me know if anyone has any ideas :P.

When you connect to the VPN, are you using internal or external DNS and does switching it make a difference?  Sometimes similar things can happen when external DNS is presented but access through the edge when on the VPN is not fully functional.  Alternatively issues can happen with given internal DNS, but full access to Lync servers is not available.

We use internal DNS when connected to the fully-routed VPN and those DNS servers are what we use internally when not connected to the VPN as well.  The same DNS servers are being used when I am able to get it to work on my Windows VM running on my Mac (which does work).  Just the Mac client is the one that isn't working.  Changing it to external DNS does not resolve the issue either (just tried). 

Some additional details - I think I have determined that the OSX user whose VPN is working is an o365 user and the rest of the users who are broken are not (which may help us pin down the issue).  Thanks in advance for any ideas you may have.