Out of all the hours I’ve spent writing cruisecontrol, ant, and nant scripts, most of them have been troubleshooting mail tasks.

In attempting to set up cruisecontrol and ant projects for our iPhone application I ran across the following error when trying to send email using gmail:

Could not Connect to smtp host: smtp.gmail.com, port 587

Fixing this was dead easy after scouring the internet. It seems that neither ant or cruisecontrol play well with gmail over 587. Changing the mailport to 465 solved the problem: