Why does Entourage flag my outgoing email as spam?

Z

zingzang

I'm trying to figure out why Entourage 2004 (and Outlook 2003) keep
flagging my messages as spam.

Background:
I run a web-based discussion forum where users sign up to participate.
I have a list of about 200 users that I want to send an annual email.
It's not spam and it won't be considered as such by my forum members -
they've all specifically opted-in.

I want to use Entourage 2004 to send out that message. I've been
testing the message, sending it to a small number of my own email
accounts on web-based systems (hotmail, yahoo, etc.). I also include
two of my own (pop3) email address that I access through Entourage on
my Mac and Outlook 2003 on my PC in my tests.

Whats happening:
Every time I send the message, both Mac Entourage 2004 and Windows
Outlook 2003 flag it as spam (neither hotmail nor yahoo mail flags it
as spam). While I do have spam protection set to "high" on both
Entourage and Outlook (and I expect most people do), I don't see what
it is about this message that's triggering the spam filters in
Entourage and Outlook.

Here are some details about the outgoing message:

In the "To" field, I use my own email address. That's the only address
in the "To" or "Cc" fields (becuse I don't want to expose everyone's
email addresses to all the recipients).

In the "Bcc" field, I've got 3 or 4 or 5 email addresses. I plan to
put all the recipents in Bcc for the final message to protect the
recipients privacy.

The subject line and the message content contain nothing that I would
expect to trigget any spam filter: nothing about Viagara or mortgages
or anatomical enhancements or any other stupid scum scam.
The message body contains a brief paragraph of plain text (although in
my final message I'd like to include a URL back to my website).
There's nothing funky in any way about the content.

So....what I'm trying to figure out is, what is it about this simple
message that's causing Entourage (and Outlook) to throw up the red
flags.

Is it because the recipient client doesn't see a match between the "To"
field and the recipent's address? If that's the case, how can one
possibly send email to multiple people while still protecting all the
recipents' privacy? I'm trying to do the right thing here....

Can anyone tell me what's triggering this and how to get around it?

Thanks.
 

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