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Certificates and RWW:  Real world ramifications of using SBS-generated or trusted authority

Posted on 2006-11-28
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Last Modified: 2010-04-19
After having run SBS 2000 server for several years and basically having remote access limited to OWA I'm about to swap a new SBS 2003 (R1) server in its place.  Knowing that RWW offers increased remote access features I'm looking to get some clarification on what I really need in terms of what seems to be an essential component of this feature: the certificate.  

When I ran the SBS setup I chose to have the server generate/sign the certificate.  A week or two ago I came across a how-to PDF for installing an inexpensive ($19.95/yr) GoDaddy.com trusted certificate in place of the SBS self-signed one.  I believe this may have been posted on ISAServer.org and consequently made reference to ISA as part of the configuration in which it would be used.  Meanwhile, I recently had an email with an SBS consultant who saw no need to use anything other than the self-signed cert.  What had me wondering if that opinion really addressed the big picture was that the PDF seemed to indicate situations/locations where the self-signed cert might not cut it or where self-signed SSL certificates weren't allowed.  Also noted was compatibility with Windows Mobile 5 devices.

We're a small company (11 people) but I do know that once the 3 partners who own the operation gain access to a new convenience like RWW they will take to it
and want unimpeded access while travelling.  They are 'gadget-aware' and may appreciate upgrading to mobile devices designed to integrate with the new configuration via a trusted cert.  Time will answer that one.  But just in terms of travelling and having unimpeded access to RWW should I be concerned that the self-signed cert may not work in some hotels, Internet Cafes, etc., or is it generally adequate in the vast majority of situations?  What are the experiences of folks who have been configuring RWW for, and using it in, the real world?

Thanks to all for your thoughts on this.
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Question by:pierc2
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Jeffrey Kane - TechSoEasy earned 125 total points
ID: 18033424
The only real advantage with a 3rd party certificate is that you don't get the warning when connecting asking you if this is a trusted connection.  FYI, the GoDaddy certificates are not automatically trusted either... since Starfieldtech (the certificate issuer) is not generally listed in the root security servers.

So, the answer is that self signed is generally adequate.  It works just fine with all mobile devices, and if they have laptops, then there is no issue at all because those would always be part of the domain anyhow.  

I've accessed my RWW from all around the world with really no problems at all.

About the only place where a third party certificate is easier is using RPC over HTTPS configuration in Outlook 2003, because most folks don't read the instructions which state that you must install the self-signed certificate (by clicking on View Certificate when the warning pops up).

Jeff
TechSoEasy

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by:pierc2
ID: 18037095
That's everything I needed to know.  Thanks, Jeff.

Brian
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by:Jeffrey Kane - TechSoEasy
ID: 18037802
You're welcome!

Jeff
TechSoEasy
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