I've used the MXToolbox Super Tool for this:
http://www.mxtoolbox.com/SuperTool.aspx .
We had a multi-point checklist for avoiding mail sent from Rails servers getting classified as spam. Some of the points had a lot of sub-detail, but it boiled down to this (in order of descending importance)
* Make sure the IP isn't blacklisted
* Send good-looking email (N.B. this doesn't mean content - it means packaging, headers, etc. This is a place where there's a fair amount of detail.)
* Use SPF records.
* Use DKIM-signing.
The rough checklist of "sending good-looking email" was,
* Use host SMTP (sendmail/postfix/qmail) instead of Ruby SMTP.
* Use the same sender and reply-to addresses.
* Give sendmail a signature address using the -f flag.