Accessing OWA, RWW without SSL Cert Error

I have a non-internet facing SBS 2003 box that has a different external name to internal.

For Example. Externally, uses can access server with remote.domainname.com, but internally they simply use http://SERVERNAME or http://FQDN.

I have setup the self-assigned SSL Certificate with the External name.

When a User accesses server either Internal or External, they are prompted within IE with "There is a problem with this website's security certificate." which can be clicked through but I would of thought that the Workstation should be trusted?

What am I missing? Do I need to install Cert on each domain PC? Do I need to setup DNS to route a request for http://SERVERNAME to http://remote.domainname.com?

So many questions .... :-)
LVL 6
FlippAsked:
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ArmenioConnect With a Mentor Commented:
The easiest way is just to add it to the root domains trusted list on each p.c.  so export the certificate
I think from IIS  then just copy it onto a usb pen and go to each pc and double click   and don't let it automatically add it to the locating it want add it to the trusted root one let me know if you need more details .
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FlippAuthor Commented:
Can this be achieves with GPO or some other automated approach using SBS 2003?
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ArmenioCommented:
I think it can  been a wile but try this

http://technet.microsoft.com/en-us/library/cc738131(WS.10).aspx

 you need to add your CA as a trusted CA
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beechy_Connect With a Mentor Commented:
The way I tend to do it with SBS 2003 is the way MS have done it themselves in 2008, create a zone in your internal DNS called remote.domainname.com (just accept all the defaults in the DNS wizard, AD-integrated etc etc), then once you'vce got your new zone, create an A record in it and leace the name field blank, so it uses the same name as the parent zone, give it the internal IP address of your SBS.  Then instruct your users to use https://remote.domainname.com whether in or out of the office.  I find users are happier with having just the one URL to remember, even if it is slightly longer to type than the internal URL.  You can either export the certificate then install it on all the PCs from a memory stick or server share, or for US$30 or so, you can add a publicly trusted certificate to your SBS from GoDaddy or similar, all machines around the world trust this certificate because they already trust GoDaddy's root certificate.
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DanMarConnect With a Mentor Commented:
IE recognises your internal cert as not signed therefore this message.  The best way around this is to purchase a certificate.  This is a requirement for OWA on Exchange 2007 so I suggest going down this path.  There are plenty SSL vendors that are fairly cheap e.g. www.digicert.com
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FlippAuthor Commented:
Thank you all for your replies to date - I will be attacking this one in the next 7 days so will get back to you with how I go.
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FlippAuthor Commented:
I would like to award points to all contributors - I have been offline for too long due to unforeseen circumstances.
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FlippAuthor Commented:
Awarded point evenly for contributing.

Ended up just using GoDaddy to get some cheap SSL Certs.
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