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Just looking for some brainstorming help.

I have a (fully updated) Windows 10 Pro desktop which I regularly connect to using RDP from a Mac running Microsoft Remote Desktop (latest version).

The Windows 10 Pro machine is using a static IP on 192.168.1.0/24 network.

When the Mac is on 192.168.1.0/24 as well, I can stay connected to the Windows 10 Pro machine for hours with no problem.

Sometimes I work from another site on 192.168.2.0/24 network. There is a wireless link between both sites. The network path is something like this:

Internet <- NAT <- Site1: 192.168.1.0/24 -> NAT -> 192.168.3.0/29 <- NAT <- Site2: 192.168.2.0/24

Whenever I try to connect to the Win10 PC at Site1 from the Mac at Site2, I can easily and quickly establish an RDP connection, and I can even use the connection just fine for anywhere from 10 - 60 seconds, and then the screen freezes and I get disconnected from the Win10 PC.

You might say, well maybe I have a problem with my wireless link, but a continuous ping from Site2 to Site1 shows no problems with the connection. Even more telling, I have another RDP server running on a Win10 Pro machine, but it is completely offsite and I access it through the Internet at Site1. In other words, from Site2 through Site1 and then out the Internet, I am accessing another RDP server also running Win10, and I can stay connected to that machine for hours on end.

So what is changing from Site1 to Site2 that is causing me lose RDP connection every time I connect? Is it a NAT problem? The weird thing I really don't understand: if I had some critical configuration or network problem, I shouldn't be able to connect to RDP at all - why is it letting me connect without problems, function without problems for about 30 seconds, and then suddenly disconnect me seemingly without reason? It doesn't make sense.

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Check if any of your network hardware is enabling priority queues. If RDP traffic is not part of the queue process it will be at the bottom to be handled. It may not just be a specific services that has priority but a specific route itself. In this case routing should be in place vs multiple NAT.

  • The NAT router on one end is an older model D-Link Wireless-G Router. On the other end is a pfsense install. I don't think it would be doing priority queueing by default, but I'll check. – Daniel Oct 2 '16 at 1:47
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I ended up flashing the D-Link router with a DD-WRT image, and the problem went away. I was using the latest D-Link firmware prior, and that was from 2010. The latest applicable DD-WRT firmware is from 2013. Either way, the DD-WRT firmware gives me a lot more control, so that's another plus.

I wanted to use an Open-WRT image, but apparently though compatible images exist, there is a 3-year-old bug for my D-Link model that prevents WiFi from working (which is important for me). Amazing that they haven't fixed it yet.

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