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Unable to RDP whilst connected to VPN

Posted on 2013-12-11
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Last Modified: 2013-12-18
Hi All,

I'm a little perplexed at the moment, i have setup a server running Hyper V with 2 VM's sitting on it. One SBS 2011 and one Server 2008 R2 with Terminal Services.

I have setup the VPN on the SBS 2011 and have successfully connected to the internal environment, but for some reason i cannot RDP to the Server 2008 R2 server.

I can:

- Ping both DNS name & IP Address
- Browse Shares
- RDP to the SBS 2011 server
- RDP to the SBS 2011 server then RDP to the Term Server.

I can't:

- Telnet to 3389 on the Term Server or RDP to the Term Server.

There is no AV or Firewall on the server...

Where can i look next?
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Question by:trentmdawson
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Expert Comment

by:Andrew Davis
ID: 39713204
sounds like the Termserver is connected to an incorrect virtual switch.


see http://technet.microsoft.com/en-us/library/hh831823.aspx

We would need to know the details of the switch. And the hyper-v host. 2008 , or 2012. Any VLan's etc..

Cheers
Andrew
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LVL 19

Expert Comment

by:Andrew Davis
ID: 39713209
Just checked on my working system, and telnet to port 3389 does not respond, so that may be a red herring.

what if you try to connect to it with /admin switch?

Cheers
Andrew
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Author Comment

by:trentmdawson
ID: 39713246
Thanks for the response.

Your right it definitely could be my Hyper V setup. First time setting up a hyper v network.. To be brutally honest it could be completely wrong.

It's a real basic setup, currently i have 3 Physical NIC's plugged in.

1 for Hyper V server
1 for vSwitch to attach both SBS & TS servers.

It shouldn't respond, should just flash the cursor. It will only bring up a message if its not working :)
PNetwork.PNG
VNetwork.PNG
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LVL 19

Expert Comment

by:Andrew Davis
ID: 39713265
Everything there seems fine.

What happens when you try to RDP? do you get anything? does it reject immediately or is it timing out?

My setup here is exactly the same (Except that i have 2012 Terminal server), the one big difference is that i am not using VPN. Is it possible to exclude the VPN as the issue by testing from another machine that is local to the LAN.

Cheers
Andrew
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Author Comment

by:trentmdawson
ID: 39713278
Yeah on the local network it works fine. Its only on the VPN where it is an issue..

Yeah it eventually times out and says cannot connect to remote server. Takes about 10 seconds to fail
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Expert Comment

by:Andrew Davis
ID: 39713283
But on the VPN you can ping the same machine without an issue?

is that correct?

Cheers
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LVL 19

Expert Comment

by:Andrew Davis
ID: 39713291
have a look at http://social.technet.microsoft.com/Forums/windows/en-US/0fc219bf-d147-4579-bea4-014fe5e65967/rdp-tunneling-via-vpn-not-working
certainly one of the most confusing write-ups i have seen, but it may provide some insight.

Personally i never use the VPN built into exchange, and instead use VPN from the router. But i understand your router may not have the ability to host the VPN. You could get Tricky and create another VM and install untangle https://www.untangle.com/ as a gateway device (it can go onto a Hyper-V, i am playing with it at the moment), then you could allow it to control the VPN.


Cheers
Andrew
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Author Comment

by:trentmdawson
ID: 39713317
Yep sure can ping the machine no problem. Both DNS names and IP.. Yeah me either but the client requested this.. May have to see if I can setup VPN on router
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Accepted Solution

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trentmdawson earned 0 total points
ID: 39718078
Problem solved....

SEP was blocking RRAS connections to other machines via RDP!
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Author Closing Comment

by:trentmdawson
ID: 39726225
Solved my own issue.
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