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TrevorWhiteFlag for United Kingdom of Great Britain and Northern Ireland

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Problem with certificates and Outlook anywhere sbs2003 to sbs2003

Hi Guys,

Its hot and I'm steaming !!!!
Problem is as follows, can anyone point me in the right direction.

I have one customer SBS2003 server running with Exchange 2003 all functioning OK. I can connect to it by VPN either from its own client machines or my own disassociated machine (which also happens to be a member of my own SBS2003 box) I can also connect to a mailbox through outlook over RPC/HTTPS no probs with and without the VPN.

At my customers second site today the plan was to install a second SBS2003 box for file storage and a SQL application (Sage ACT!) users would continue to use mailboxes on the remote SBS2003 box. Before I installed the SBS2003 domain here I was able to connect to the remote SBS2003 email service. Now I can't, well not sensibly anyway.

I can connect to the remote SBS2003 site with a VPN and setup the outlook exchange profile using the control panel applet (mail) This on a W7 pro 64bit workstation joined to the local domain. If I try to run outlook to gain access to the remote account it always prompts for a password which is accepted but followed by the dreaded Proxy server certificate warning.

If I close the certificate warning and leave the VPN open the account connects. If I drop the VPN no connection is made.

Also checked for the certificate being installed by using an elevated instance of IE and using HTTPS://server.domainname.co.uk/exchange this gives the certificate error warning and allows you  to install the certificate in the trusted root folder, it says it succeeds but I never see the certificate installed and the page can not be displayed without the cert error.

I even tried importing the certificate from my machine to the domain workstation, this certificate didn't succeed installing either, despite saying it was successfull.

Whats going on here guys, I'm running out of time fast and have spent all afternoon on this already. Am I trying to do the impossible ????

 I have run the internet and email wizard again and told it not to configure email. This had no effect but have left in this mode.


Any thoughts would be helpfull.
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Avatar of Cliff Galiher
Cliff Galiher
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Hi, thanks for your time.

Well we didn't actually buy this product for the job, it was already here, all I did was do a ground up install with an existing licence.

I knew about the only one domain restriction. But I can connect to the same remote exchange server from my SBS2003 network - I tested it before I did this. So believed it was possible.

The evidence here is as you say though, if I detach the user from the domain and create the Outlook connection (RPC/HTTPS) all is fine, if I connect to the SBS domain and try to connect over an outlook connection established with a domain account it fails. Also it will not install a certificate in the trusted root folder.

Looks like I have to shift the currently remote mail over to this server (or cloud) and go from there. Thanks for your time again. I guess the points are yours :-)

Still not sure why my workstation manages to perform i this regard.

REgards
Oops didn't get back to this. I resolved the above problem as indicated by separating the mail domains so that each site hosted its own mail. This is fine for the time being - we will rollout Server 2012 shortly.

Thanks Cliff for your input - I'll award the points as it id stop me banging my head. Would love to know why my SBS workstation could access the second domain though!

REgards
As per my last post