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To create and use Digital Signature see Getting Started with S/MIME on Entourage
Entourage will never send or receive cookies for privacy reasons.
2) How do I prevent Entourage from giving out ANY information other than the letters I post to the web?
If you have selected to viewi remote images in-line, then it's possible for an embedded webbugs to send back information to the sending party.
Throwing Entourage in the trash won't do any good. You're seeing the scourge of HTML mail -webbugs specifically. Usually HTML img tags with tracking information in them. They typically display 1 pixel images (that you therefore never see). These are used to confirm that your email address is valid. Once it's been validated, the list retailer can sell it for a higher price.
One way to reduce your spam over time (a long time - you've now probably let dozens of email list retailers know that your email address is valid): In the Mail & News Preferences/Read tab, turn off View Complex HTML. Then, whatever you do, don't click on those really long URLs that appear in your junk messages.
In Entourage 2004, check the new Security Preferences:
Entourage 2004 uses the IE engine.