Get Off Blacklists
If your email server is on a blacklist, it becomes extremely difficult to reliably send email, especially to new people on your lists.
The first step is to check if your email server is on a blacklist, following are a few free services:
If you find that you are on a blacklist, you will need to follow up with the website that has added you to their blacklist. That information is provided by the tools listed above.
Make Sure Your DKIM, SPF, Sender-ID and Domain Keys Are Setup Properly
You will want to make sure your email server supports these protocols (DKIM, SPF, Sender-ID and Domain Keys) and that they are properly implemented.
This alphabet soup helps ISPs determine the authenticity of your email from a technical perspective. To make sure yours are setup properly try using IsNotSpam.com