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Intermittent RDP

I have been working on a client’s ASA 5510 v8.2(1) with setting up Anyconnect for the PC (domain and non-domain), Iphone/pad, and android, which in itself is pretty straight forward that I have done before for other clients. I am running into something strange when using RDP over the VPN and hope this makes sense to someone.

Anyconnect is setup with LDAP authentication, DAP to check a security group for the users allowed to connect, and the internet traffic is set to Tunnel All and is working correctly. When I test the VPN on a domain laptop with a separate internet connection from the office and logged in as a domain user I can ping and UNC by name and IP to computers inside, along with being able to RDP. I also test the VPN on an iPhone and android which can RDP to computer on the inside.

The problem is that sometime in the evening (anywhere from 6:30 to 10p) I am still able to connect to the VPN on iPhone, android, and a non-domain computer and ping and UNC, but cannot RDP to anything inside (made sure the systems I am trying do not sleep). Looking on the ASDM Real-Time Log Viewer I can see a built TCP for 3389 and then teardown. Even telnet <inside-computer> 3389 fails on the remote system.

However, when I log-in to the VPN on a domain computer as a domain user I can once again RDP to any computer and afterwards also once again able to RDP on the iPhone, android, and a non-domain computer over the VPN for a while and then stops after a period of time.

Any Suggestions?

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