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 email@example.com, shoots me emails all the time, and Postini let's them through. Yet, somehow, when GroupMail utilized the same email address, firstname.lastname@example.org, 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?