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Thanks for the great feedback.
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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, &quot;You have a case next week, make sure you submit all necessary materials.&quot; &nbsp;<br />
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Here's my big concern: One of the gals in the office, Michele, periodically uses GroupMail. &nbsp;She was having trouble with it last week. &nbsp;In the process of debugging, I shot off a bunch of emails to the GroupMail test group of which my email address belongs. &nbsp;Here's what rattled me: my Postini spam filter flagged the emails as spam. &nbsp;Michele, at michele@fakedomain.com, shoots me emails all the time, and Postini let's them through. &nbsp;Yet, somehow, when GroupMail utilized the same email address, michele@fakedomain.com, Postini recognized that the email was automated and identified it as spam.<br />
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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. &nbsp;<br />
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Can someone point me to some literature on this or give me some guidance on this?
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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?

Understanding Spam Filters

Various techniques are used to prevent email spam (unsolicited bulk email). No technique is a complete solution to the spam problem, and each has trade-offs between incorrectly rejecting legitimate email (false positives) vs. not rejecting all spam (false negatives) - and the associated costs in time and effort. Anti-spam techniques can be broken into four broad categories: those that require actions by individuals, those that can be automated by email administrators, those that can be automated by email senders and those employed by researchers and law enforcement officials.