RDP over VPN Failing to Win8

Nikumba · 14 May 2013 at 10:30

Have a bit of a head scratcher with this one.

We have a customer that is using SBS 2011 along with a mix of XP, 7 and 8 client machines.

The user has an XP machine at home which connects to the SBS via VPN, then he wants to be able to RDP onto his Windows 8 office machine.

This is not working at all, it fails to connect both by DNS name and IP address, however the XP machine will connect fine to the SBS server and to other client machines on the network.

We can also connect via RDP from the SBS server to the Windows 8 machine.

We really have no idea why this is happening and wondered if anyone could have any suggestions.

With the VPN running we can pink from XP to SBS and SBS to XP, the home IP range is also different to the SBS range

Cheers

Kimbie

tribz · 14 May 2013 at 10:48

Does he have the latest version of the RDP client installed on his XP machine?

Just FYI, he could also connect in via RWW with SBS2011.

ruffneck · 14 May 2013 at 11:14

Windows firewall on the Windows 8 office machine set to allow RDP connections from the home IP range?

Goliath · 14 May 2013 at 11:59

There was a known issue with one of the security hotfixes released last year where it borks Win8 connections, MS12-020 (we had similar issues until the security patch was re-applied).

Saundie · 14 May 2013 at 17:25

Nikumba said:
We can also connect via RDP from the SBS server to the Windows 8 machine.

The way you phrased this leads me to believe you're connecting to their SBS box via RDP, then hopping over to the Windows 8 client? If that's the case, can you connect via VPN from one of your clients? Also, what error message does he get when connecting from his XP client?

blastman · 15 May 2013 at 17:45

ruffneck said:
Windows firewall on the Windows 8 office machine set to allow RDP connections from the home IP range?

surly once a vpn connection has been established he'll have a ip from inside the work network. not a home ip.

has he enabled 'allow less secure connections' from the remote settings on the windows 8 machine?

win 7 will use a more secure rdp connection where as xp is an older less secure one. you have to manual state that it's ok to connect to a windows 8 from a less secure rdp session

visibleman · 15 May 2013 at 18:24

As Blastman mentioned, make sure "Allow connections from computers running any version of Remote Desktop" is selected on the W7/W8 system if you plan to connect from XP.