After fighting with mail server configuration for months, I tried using JIRA's option to connect to Gmail, and amazingly it worked right out of the box, with nothing required on the server.
However I am unable to set up SMTP servers the same way for Confluence, FishEye, Bamboo or Stash. All of them time out and fail to send a test message with various errors. Confluence gets the proxy error below, for example, even though the settings are the same (as much as possible, given the limited fields Confluence provides).
How does one resolve the differences in mail server setup options between tools and get them all to work like JIRA? Or if possible, is it possible to share a single JNDI configuration between all tools?
