RDP doesn't work over VPN

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At work (192.168...) I've created a peer-to-peer IPsec VPN to another site (172.16...) with the intention of RDPing on some remote machines. This tunnel remains open all times and the RDP works when I'm at work.

However, when I try to VPN to work (eg from home) in order to do the RDP, this fails. I get an IP from the work DHCP and I can see I use work's gateway as expected, but still no RDP.

What am I missing? Is there a problem with essentially using VPN over VPN in order to RDP?

T.Rfing

Posted 2016-07-04T09:28:39.610

Reputation: 3

1What's your home DHCP range? If work is 192.168.1.x and home is also 192.168.1.x then it's to do with routing because your computer can't find the RDP client. Change your home DHCP range to, say, 192.168.5.x and see if that works – Kinnectus – 2016-07-04T14:38:35.670

Answers

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There is no problem to vpn to use a site-to-site vpn.

HOWEVER, when you setup a site-to-site you allow certain IP's from your local traffic (office 1) to be allowed to the remote site (office 2) When you vpn into the office (office 1) from home, you get a DIFFERENT IP RANGE, so the site-to-site vpn won't allow you through to the remote RDP (office 2) because you are coming from an not-allowed IP range (home).

Login to the vpn from you home to the office (office 1), then RDP to a machine in your office (office 1), and THEN rdp from there to the remote machine (office 2).

warhansen

Posted 2016-07-04T09:28:39.610

Reputation: 329

Thanks! I'll do that as a workaround. Isn't there any way of telling my office1 router to route any vpn incoming requests so that they get put through to the office2? – T.Rfing – 2016-07-04T14:52:43.407

I have not done this myself but I imagine if you allow the IP subnet you are giving out through the vpn from your home, to the remote site it should work. Test this only when nobody else at work though... :-) – warhansen – 2016-07-05T13:12:06.327

Asked: 2016-07-04T09:28:39.610

Viewed: 968 times

Active: 2016-07-04T09:36:10.067