Redmine

Hey all, I am having an issue where when I update a issue ( update is the only thing on for email btw), it hangs for around 15 seconds then sends the mail. I'm out of ideas here. I did a tcpdump on port 25 and it is getting to the mail server without issue, and then 15 seconds later it is finishing the connection. The email goes though without problem from there. All other users on this mail server are working fine without delay. I can't find any errors in any logs on either the redmine server or the mail server. I am a bit at a loss as what to do. Also, every once in a while, when you update a issue it will throw an error with this

Application error
Rails application failed to start properly

This started at the same time, so I'm not sure if it is related.

The box is osx leopard and it is running through apache.