How do I troubleshoot email notifications?

After upgrading my server from 2.0 to 2.0.0.1 my email notifications don't get sent. Is there a set of things I should check are set properly, and a way to cause a test to be done so I can see if I receive emails?

From my server's admin page on the "e-mail settings" section, I have the following settings:
enable email notification: true
SMTP server: (same server as my email client)
SMTP server port: (same port as my email client)
SMTP username: (same username as my email client)
SMTP password: (ditto)
restrict to whitelist: false
whitelist: <empty>
email from address: my email id
email from name: my name
SMTP reply address: my email id
use STARTTLS: true (but have tried false also)