Ruby On Rails sending SMTP mail fails, howto debug?

Question

Hi, I am really really new to Ruby On Rails, so I think it is a easy question.

I am setting up a OpenSource RoR application on a testing server. However couldn't get it sending email though our Exchange server. The testing server and Exchange server are both set correctly, I can test that using other web application on the same server.

However, I spend hours and couldn't get this particular Application (ticket_mule) sending email. Now in errorlog, it will show:

Net::SMTPSyntaxError (501 5.5.4 Invalid Address):

Which is not very helpful for me, as I am not even sure which address it meant: SMTP server, sender email, receipt or webpage?

The web app is using ActionMailer, and by reading the code, I've changed various of SMTP settings in environment.rb, and domain settings in config.yml and its notifier.rb code as well, but it just wouldn't work. I am pretty sure I know the right SMTP settings. But the problems is that this particular application have different settings in different places which I think may related to my problem.

I think I really need to know a better way to debug it besides looking at error_log.

Thank you in advance!

Answer 1

Since you're using Exchange, I think you're running into a UNIX/Exchange problem This Article describes the 5.5.4 Invalid Address.

To "prove" you could:

> telnet a1.psgroup.com 25
Response:
220 a1.psgroup.com Microsoft ESMTP MAIL Service, Version: 5.0.2195.1600 ready at Wed, 28 Feb 2001 16:18:08 -0500 
HELO mail.luminate.net.
501 5.5.4 Invalid Address

It has a workaround if you have server access to exchange.