SBS2008 Remote Desktop Problem

Tesla · 28 Aug 2015 at 16:25

Hi all,

Have spent a few hours on the following and have made little progress, I think I'm at the point where I need to take a step back and revisit the problem with fresh ideas. I'm hoping some external pointers could be of help too...

A basic SBS 2008 setup running Remote Web Workplace.
~6 office PCs.

Remote access is seldom used by the staff but at time of last use, some 6-9 months back perhaps, worked fine via RWW. It's now not working.

Now, when attempting to connect via RWW I mostly receive:

On occasion, I've instead received:

If I attempt to connect via Remote Desktop (with RD Gateway configured) I receive:

I can Remote Desktop around the internal LAN between server and PCs, and vice-versa.

WAN Ports 25, 443 and 987 are open and forwarded to the server.

I've tried connecting from multiple client machines, Windows Vista, 7 and 10. All produce the same error.

I've ran "Fix my Network" in the SBS console.

Any ideas would be very welcome and appreciated!

jameshurrell · 28 Aug 2015 at 21:26

Some suggestions here might be worth a try:

http://blogs.technet.com/b/sbs/arch...connect-to-a-computer-issues-in-sbs-2008.aspx

seems a ssl cert error might be to blame.

tribz · 29 Aug 2015 at 12:32

Connecting to the server or the workstations via RWW?

If workstations, check the rdp ports are open on the client windows firewall settings. A couple of my SBS sites have had them disabled, by what I'm not sure but I presume an update.

Rob7865 · 1 Sep 2015 at 13:07

Make sure you've added the RWW Site to IE Comparability list. Can you Remote Desktop to the Server using the Gateway Address? This way you will know the Router is Port forwarding 443 correctly.

Are you using a self signed SSL Cert?

Rob

Liquidfox · 10 Sep 2015 at 13:37

If you're using the self-signed cert you'll need to add it to the Trusted Root Certification Authority, or run the SBS Installer found in the Public Downloads folder.