I have a user who can not send mail to ONE specific person. Everyone else in the organization can send mail to the recipient. I have exchange 2007 in a one-server configuration. The user receives the same error from multiple computers and both OWA and Outlook. The (editted) error message that is returned is: #< #5.7.1 smtp;552 5.7.1 Content-Policy reject msg: Message rejected; S3174301AbXHFRKu> #SMTP# Original message headers:Received: from mail.mydomain.local by mydomain.com with Microsoft SMTPSVC(6.0.3790.3959); Mon, 6 Aug 2007 13:11:44 -0400 Received: from mail.mydomain.local by mail.mydomain.local with mapi; Mon, 6 Aug 2007 13:11:44 -0400 From: User <user@mydomain.com> To: "recipient" <user@recipientdomain.com> Date: Mon, 6 Aug 2007 13:11:43 -0400 Subject: Test Email Thread-Topic: Test Email Thread-Index: AQHH2Ezcx/K9fhO4tUC4gclXWHOEQg== Message-ID: BCFE1F4E8C878E4789512326BF7B16C8E6A55460@mail.mydomain.local Accept-Language: en-US Content-Language: en-US X-MS-Has-Attach: X-MS-TNEF-Correlator: acceptlanguage: en-US X-OriginalArrivalTime: 06 Aug 2007 17:11:44.0640 (UTC) FILETIME=[DD5E3000:01C7D84C]

Can you clarify whether the recipient is in your organization or is external? And if external, have you contacted their IT group to see if there is any type of blocking or content filtering they are doing that could be causing this? Because based on what your headers are showing, it looks like it is being rejected by the remote domain mail server... Lee

The recipient is external. Their IT Group says it's not them. The user can also send to anyone else at the same domain - not just this ONE address. What's interesting to me is how quickly the response is generated, it's instantaneous - and it says it's coming from my server... only I'm not filtering anything outgoingbased on content. Where do you see that it's being rejected by the remote server? I might just be missing something...

Sorry for delaying in responding.... Ok, nevermind the remote server bit... looked at one thing and my mind saw another... I'm guessing you've checked any transport rules on the Exch2007 that you do have set very closely to make sure nothing could be causing this? And if there is nothing there, then when you do send an email out, does it go directly from your E2007 out to the remote mailhost on the Internet, or are you sending to a smart host (either internal or external) for that delivery? And by any chance is it doing any filtering?

Actually, afterspending the day pouring over the SMTP logs I found the last good message that the user sent to the recipient and then found the first blocked message. According to the SMTP log, the recipients server blocked my user (if I'm reading it right)... <recipient server IP>- OutboundConnectionResponse [27/Jul/2007:16:40:36 -0500] "- -?250 2.7.1 Content-Policy accept-into-freezer-1 msg: Message is spam; even though the later messages read a different error (552 5.7.1) it looks like it all started here... your thoughts? and thanks for your interest!