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I've setup a Win2k8 R2 RDS Gateway. It works great but the initial connection takes 10-20 seconds. I've had a hard time finding troubleshooting ideas for the problem. Anyone have any suggestions on where to start or common issues?

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DNS is my guess!

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What part of the name resolution process would cause it to be slow but not to fail? – Steve Evans Nov 11 '10 at 0:23
Reverse dns perhaps.. ive seen this problem before ( waiting until it fails ) im not exactly sure.. but its where i would start looking – Arenstar Nov 11 '10 at 0:35

We had this problem and ended up virtualizing Remote Desktop Gateway on its own VM under Hyper-V. We isolated it away from our other server functions, and it sped it up as far as connections go.

We recently installed a VPN (Remote Access Server role) for sstp traffic, and we noticed our VPN connection happens a bit quicker than the RDP one through SSL.

Our advice to you would be to build a box in a lab environment with only this service loaded and the appropriate certificate to see if something else is perhaps slowing it down.

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