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SBS 2008 on a vSphere virtual Machine

Posted on 2010-08-21
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Last Modified: 2012-05-10
Hi,

I am trying vSphere to run some virtual servers. I have installed a virtual SBS 2008 std.
Everything is working as expected with the SBS 2008 server, except that I can not connect to it via RWW.
I can VPN and RDP to the server from an external client, but not via https://remote.mydomain.com/remote.
I have published a host record (remote.mydomain.com) which points to the public IP address of the server.
This is my configuration:
Watchguard Edge10e Hardware firewall
Public IP 82.144.x.x
Private network 192.168.16.1
Port 3389 redirected to 192.168.16.3 (the SBS2008 running on virtual machine)
Port 1723 redirected to 192.168.16.3
Port 987 redirected to 192.168.16.3
Port 25 redirected to 192.168.16.3

Physical box hosting VMware vSphere, static IP: 192.168.16.2
Laptop running Sphere Client, static IP: 192.168.16.10
Virtual machine with SBS 2008, static IP 192.168.16.3
DHCP on SBS running, first IP for scope is 192168.16.11

I have internet access from the SBS2008 server and can VPN as well as RDP to it from external network.
I can telnet to port 25 and Exchange reponds.
I just can not connect to it via https.
It is driving me crazy!

Any one have any ideas where I might be going wrong with this setup?

Thanks in advance.
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Question by:caratech
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markzz earned 500 total points
ID: 33494013
I'm making the assumption you can successfully connect to https://192.168.16.3/remote from the internal network.
Therefore it's not an SBS functionallity issue or an ESX issue????

First guess is your Watchguard Edge10e is getting in the way.
Is your Watchguard Edge10e listening on 80 and 443 for management reasons on Public IP 82.144.x.x

Remove the firewall rules which forward 443 and 80 to your SBS Server, now try to telnet on 80 and 443 from the internet to your external IP.
Command would be "Telnet 82.144.x.x 443"
If you establish a session your firewall is the cause, if you can't establish a session you can rule out the Watchguard firewall.
Please test and report back.
 
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Author Comment

by:caratech
ID: 33494650
Thanks for the reply.
Yes, I wad able to access the site from inside the network and as I was sure the watchguard was forwarding port correctly I could not see what it wannest working.
I am using a self certify certificate (from sbs) I although I got an error from the client complaining about the certificate and I installed it on my xp client, i dint think that was the problem. I have reinstalled the certificate on the client using the certificate installer and thas has resolved the problem.
Thank you for your input.
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Author Comment

by:caratech
ID: 33995929
In the end I decided to get a certificate from GoDaddy which has resolved the issue. Thanks for the reply.
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