some email sent using Entourage arrives in other peoples Junk Mail.

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I am having an issue that I believe is tied into Microsoft Entourage 2004 for Max OS X 10.4.10. What I have found is when an employee using Entourage sends another employee (in house) an email address; it sometimes will go to the employee’s junk mail folder. Our network consist of about 99% windows computers and we use Microsoft Exchange 2003 for our mail server.

For the test we conducted, I had the Mac employee send my email address an email message with a small basic PDF file consisting of just a logo. I did receive the message, but it went to my junk mail folder.

I had that same employee send the same message and attachment using the web based side of our email server called outlook web access. It is basically like hotmail, or gmail.

That email message arrived to my inbox as it normally would.

Would there be a setting in Entourage that could “pollute” a simple email message that would possibly cause to be flagged by our junk mail filter. This situation also happens to outside clients that our Mac employee sends email too.
 
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Mac Mini Core i7 2012 | White 2009 MacBook 2 Ghz | 733 Mhz G4 Quicksilver
I have the same issue sometimes on an internal network (I am working at Bosch at the Mo)

There is no logic to it, the users are in the global address book on the exchange server and have a Bosch email domain

I don't think Entourage's junk mail feature thinks that email coming from your own domain is not necessarily safe?
 

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