A colleague just responded to a digitally-signed Email that I sent him indicating that my signing certificate was expired. I am using Outlook 2010 and am very surprised that the client was not smart enough to at least warn me that my currently-selected cert was expired! Granted, I have kind of a unique situation in that I have multiple certs in my CAPI store. Is this normal behavior? Am I going to have to train my users to be aware of this (taking into account that most of them don't even know what certificates are)? This is a significant design flaw IMO.