Here is what the self-issued certificate in SBS 2008 looks like via the certificate management snap-in:
SBS 2008 Self-Issued SSL is good for 2 years
The fact that the certificate is only good for two years is important.
If a client decides against a third party certificate, then the network audit notes need to reflect the expiry date of the certificate. A reminder should be set in Outlook or client management software for a month or so ahead of the expiry to speak with the client about obtaining and installing a third party certificate.
Why third party? Because the need to have every non-domain joined workstation run the little SSL install routine could get to be quite expensive over time. And, getting a Windows Mobile device to run with the self-issued certificate may turn into a nightmare depending on the provider the device is connected to.
We use Comodo for our single SSL certificates and DigiCert for our wildcard certificate needs. They may not be the least expensive, but we get to talk to real people if we get into some sort of pickle.
Microsoft Small Business Specialists
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