Have you checked the alert and subscriptions in server.
first setup smtp settings and then go to alerts and subscriptions page in configurations and check alert and subscriptions
Everything looks like it's set up correctly, but it's just not sending out the emails. Do you have to set up the SMTP account into Outlook as well?
It looks like it's not working because our Office365 server does not accept encrypted connections. Has anybody gotten this to work with Gmail, Hotmail or some other service?