Had a similar problem while testing. The two things to check are: (1) Make sure the web.xml doesn't have the mail session resource commented. (2) Make sure you don't have a duplicate copies of mail.jar and activation.jar in both Tomcat's common/lib and the app's WEB-INF/lib. Put them only in common/lib. It's really easy to end up with a duplicate, so I added a note on the upgrade guide about this.
Matt Raible wrote:

I haven't got any comment e-mails from my site since I upgraded to
Roller 2.0.  I have everything configured correctly AFAIK.  The UI has
the appropriate boxes checked in my settings, as well as the server
settings.

Matt



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