asked on

Email not being delivered, getting flagged as SPAM...#5.7.1 smtp;550 5.7.1 Message rejected as spam by Content Filtering

I have one user that is using mac os 10.4 and entourage 2004.

Whenever they send to this outside email address it gets sent back with this error:

Your message

To: Justin Huntington
Cc:
Subject: Website
Sent: Thu, 10 Jul 2008 11:50:54 -0700

did not reach the following recipient(s):

Justin Huntington on Thu, 10 Jul 2008 11:53:16 -0700
You do not have permission to send to this recipient. For
assistance, contact your system administrator.
<wireflydc.wireflyit.local #5.7.1 smtp;550 5.7.1 Message rejected as
spam by Content Filtering.>
________________________________________
Reporting-MTA: dns; phxex01.corp.mountainsidefitness.com

Final-Recipient: RFC822; justin@wireflyit.com
Action: failed
Status: 5.7.1
X-Supplementary-Info: <wireflydc.wireflyit.local #5.7.1 smtp;550 5.7.1 Message rejected as spam by Content Filtering.>
X-Display-Name: Justin Huntington

------ End of Forwarded Message

I do not have them being blocked on the server they are sending to (wireflydc)...in fact the entire domain is allowed in the content filtering.

I am not sure as to why this person cannot send to wireflyit.com, as every other user in the organization can, just not this mac user....

Pcobiwan

Content filtering means that something in the email itself or in the email configuration is setting off the blocking. for instance we use a third party SPAM blocking filter and have it set to reject emails that were created using a foreign character set.

Perhaps the format of the email (since it's MAC) is different than what you have your Exchange server or third party blocking set to accept.

Justin H

ASKER

We use Sunbelt Ninja Spam filtering on the exchange server that is sending the message. Also we have enabled the anti spam scripts that typically reside on the edge server, however you can run the scripts from the EMS instead of having a seperate edge.

On the server that the message is destined to, there is Trend Micro..but it is allowed at the domain level.

Can you see if its the sending server or the receiving server that is stopping it?

Pcobiwan

If you can run a mail trace it should give you an idea of where it's getting stopped. I'd also check the headers on the bounce message.

Looking at the message you posted above it states that 'you do not have permission to send to this recipient.' That leads me to believe that it is the receiving server as that is where the recipient would be looked up.

Can you run a traceroute from the user's client to your server?

Justin H

ASKER

i could, but then again its a mac...not sure how to run a tracert on a mac....ideas?

Pcobiwan

Try this:

http://www.verio.com/support/documents/view_article.cfm?doc_id=3693

Justin H

ASKER

and after that, what would this tell me? sorry for being such a doof...

Pcobiwan

Nah - email issues are always a bear ;) When you run the tracert it should have given you a report back on every hop from the client to the server. Where did the tracert stop - your client's outgoing mail server (that would be a really short report!) or your incoming mail server? Are there any errors showing up between the two?

ASKER CERTIFIED SOLUTION

Justin H

membership

This solution is only available to members.

To access this solution, you must be a member of Experts Exchange.

Start Free Trial

Pcobiwan

I'd check the original email then. Look for basic stuff in the headers (i.e. foreign character set being used) and in the content.