With Microsoft's impending end-of-life support for Windows 2003 and all the recent SSL attacks, it looks like moving to SHA-2, TLS1.x, etc. is inevitable. I've previously had an impossible time getting Dragonpay to work correctly on Windows 2008 R2 64-bit at Softlayer. But this time around, when I had the OS reloaded for Windows 2012 64-bit, it was surprisingly smooth. Granted that it took a little bit of getting used to the new interface, but it wasn't that much different from Windows 2008.
Figuring out where to find the SMTP service took a bit more of a challenge but I found this incredible and very detailed step-by-step guide that worked perfectly:
http://blog.hyperfive.com/2013/07/how-to-setup-internal-smtp-service-for.html
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