Jeff Atwood has a good post on ways to pass email spam filters in his post at: http://www.codinghorror.com/blog/2010/04/so-youd-like-to-send-some-email-through-code.html
The only issue I have is figuring out a way to sign the email with a private key for DKIM. We use the MailMessage and SmtpClient objects that come with ASP.NET 3.5. How can I sign an email with these objects?
Also, we use the free SMTP Server that comes with Windows 2008 R2. I don't believe there is a way to sign from that server, if there is way I'm open to using that approach.