Understanding Spam Filters

I'm going to build a small SQL Server / .NET based app in the next month that loops through our firm's client database, identifies pending cases, and shoots off automated emails to clients that state, "You have a case next week, make sure you submit all necessary materials."  

Here's my big concern: One of the gals in the office, Michele, periodically uses GroupMail.  She was having trouble with it last week.  In the process of debugging, I shot off a bunch of emails to the GroupMail test group of which my email address belongs.  Here's what rattled me: my Postini spam filter flagged the emails as spam.  Michele, at michele@fakedomain.com, shoots me emails all the time, and Postini let's them through.  Yet, somehow, when GroupMail utilized the same email address, michele@fakedomain.com, Postini recognized that the email was automated and identified it as spam.

My big concern: I construct this tool that shoots off individual emails to our clients, but our client's spam filters somehow identify the emails as automated and flag them as spam.  

Can someone point me to some literature on this or give me some guidance on this?
jdanaAsked:
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Sudeep SharmaConnect With a Mentor Technical DesignerCommented:
The best way to identify why postini is tagging your emails as spam is by getting the email headers/ internet headers of the email which are getting blocked by Postini and scan them to the Postini's Message Header Analyzer utility. The link below also detailed how to extract the headers of the email:

http://www.google.com/postini/headeranalyzer/

This would give you insight.

Another way is to open a case with Positni support and asked them for the reason of emails been blocked. you could also ask them how to fix it.

http://support.postini.com

In my experience your application uses external IP and a domain which is not real (fakedomain.com) so there are various check all the email services are Postini does, like RDNS check, SPF recrods, correct helo command (as per RFCs) etc. So I believe your domain are lacking many if not all the feature which should be there and hence they are marked as spam.

I hope that would help.

Sudeep
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jdanaAuthor Commented:
Thanks for the great feedback.
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