After spending the past three weeks thinking in depth about self-issued certificates in Windows Small Business Server 2008, I started to think about Small Business Server 2003, and it's self-issued certificate.
The default self-issue certificate is valid for 5 years. SBS 2003 came out in 2003, 5 years prior to 2008.
So, those early adopters out there, if you're still using a self-issued certificate, maybe you should consider putting a reminder in your calendar for when yours expires.
Before it does expire, you should run the Configure E-Mail and Internet Connection Wizard. Through the wizard you can choose not to change anything, but when you get to the certificate section, select generate a new one. Once you do this you will have to re-distribute the certificate in \\server\clientapps\sbscert\sbscert.cer to all your client PCs (I believe domain joined clients will get it by default), and you'll have to manually distribute it to your home clients, and windows mobile devices. Makes buying a trusted certificate more appealing doesn't it? :)
If you do buy a trusted certificate wizard, and you have Windows Mobile 5 of previous devices, make sure that cert works with your devices!
Happy 5-year reunion.