Following @shanselman's article on remoting into an Azure VM for development, I spun up my own VS 2013 VM, and that image runs on WS 2012.

Once I was able to remote in, I started installing all my dev tools, including Tortoise SVN 1.8.3 64bit.

Things went south once I started attempting to check out code from my personal svn server. It would hang and freeze often, although sometimes it would work - I was able to partially check out projects, but I would get frequent connection time out errors.

My personal svn server (VisualSVN 2.7.2) runs at home on a windows 7 machine, and I have a dyndns url pointing to it. I have also configured my router to passthrough all 443 traffic to the appropriate port on the server. I self-signed a cert and made sure it was imported into the VM cert store under trusted root authorities.

I have no problems connecting to my svn server from 4-5 other computers & locations.

From the Azure VM, in both IE and Chrome, I can access the repository web browser with no issues.

There are no outbound firewall restrictions.

I have installed other SVN add-ons for Visual Studio (AnkhSVN, VisualSVN) and attempted to connect with my svn server, with largely the same results - random and persistent connection issues (hangs/timeouts).

I spun up a completely fresh WS 2008 Azure VM, and installed TortoiseSVN, and had the same results.

So I'm at a loss as to what the problem is and how to fix it. Web searches on tortoisesvn and windows server issues doesn't yield any current or relevant information.

At this point, i'm guessing that maybe some setting or configuration that MS Azure VM images is the culprit - although I should probably attempt to spin up my own local WS VM to rule out that it's a window server issue.

Any thoughts? I hope I'm just missing something really obvious!