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Error #4.4.7 in Exchange 2003

I have SBS 2003, running Exchange 2003 on it, AD, DNS setup correctly.MX working correctly, RDNS setup, NAV 10.1.
That is my setup. Now my problem is that recently i have started to get a lot of #4.4.7 NDR with any email that has any sort of attachment (gif, pdf, doc, jpg.....) if i zip any of these attached files all is ok and it goes through.
I did not have to do that couple of weeks ago. If you can think of anything i need to look at please do advise me.

Your message

  To:      someone@hotmail.com
  Subject: check this out too funny.
  Sent:    Fri, 20 Jun 2008 10:13:20 +1000

did not reach the following recipient(s):

 (someone@hotmail.com) on Sat, 21 Jun 2008 10:17:12 +1000
    Could not deliver the message in the time limit specified.  Please
retry or contact your administrator.
    <mail.psc.edu.au #4.4.7>
Reporting-MTA: dns; server.psc.local

Final-Recipient: RFC822; someone@hotmail.com
Action: failed
Status: 4.4.7
X-Supplementary-Info: <mail.psc.edu.au #4.4.7>
X-Display-Name:  (someone@hotmail.com)

someone on Sat, 21 Jun 2008 10:24:37 +1000
    Could not deliver the message in the time limit specified.  Please
retry or contact your administrator.
    <mail.psc.edu.au #4.4.7>
Reporting-MTA: dns; server.psc.local

Final-Recipient: RFC822; someone@ogilvy.com
Action: failed
Status: 4.4.7
X-Supplementary-Info: <mail.psc.edu.au #4.4.7>
X-Display-Name: someone


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adnan007
Asked:
adnan007
1 Solution
 
jenkinsmeCommented:
How is your server sending e-mail? Do you have a static IP address and using your server for SMTP or are you relaying your outbound e-mail through a webhost/ISP using smarthost?
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adnan007Author Commented:
I have a static IP address and email is being delivered through our SBS 2003 DNS, using SMTP connector.
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Network_Data_SupportCommented:
This message usually indicates an issue on the receiving server. Verify the recipient addresses, as well as whether the receiving server is configured to receive messages correctly. Resending the message places it in the queue. If the receiving server is available, message delivery succeeds.

You say that when you ZIP the attachments they are sent, there is no Size limit or extension settings on the receiving server?
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adnan007Author Commented:
I would not know if there was any limits on their servers, It happens to any domain i send emails to. Today i got about 20 NDR with #4.7.7 only because here was a pdf attachment on a email msg. The size of attachment does not matter 100kb or 7MB. Can it be antivirus?
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kieran_bCommented:
could be anti-virus, it could equally be the greylisting bug;

http://technet.microsoft.com/en-us/library/aa998772.aspx
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adnan007Author Commented:
hi kieran and thank you for reply
i have not been greylisted and this queuing only happens to emails with attachments. anything without attachment  to any domain goes through. if it is antivirus how could i go about resolving it.
i have NAV v10.1.5
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kieran_bCommented:
>>i have not been greylisted

How would you know that?  But I agree, it sounds less likely due to the attachments.

>>if it is antivirus how could i go about resolving it.

Uninstalling the AV, rebooting and seeing if the problem is gone is a good start.
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adnan007Author Commented:
since this problem started to show i hvae checked whitelists, greylists, blacklists, yellowlists and all other lists that exist out there in our know and unknown cyber universe :)
Uninstalling AV is the only option i have not done, i guess sometimes the simplest solution stares at your face.
Thank you kieran and as it is saturday today i will get back to you on monday and update you on what happened.
Thank you again!
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kieran_bCommented:
>>since this problem started to show i hvae checked whitelists, greylists, blacklists, yellowlists and all other lists that exist out there in our know and unknown cyber universe :)

Aha, but that is just it - My server greylists, and what that means is that it rejects ALL mail from EVERYONE.

Why?  Because legitimate mail servers will always try again, spammers don't.  If you sent me a mail, my server would reject it, your server would wait 60 seconds and then try again - bam, I have mail.

It is not elegant, and crap servers like Optus cause some shocking delays, but it is a killer for spam.
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adnan007Author Commented:
hi there kieran,
i hvae uninstalled NAV and that didint fix the problem. i have set the glitch interval setting that i didnt have before and now i will wait and see if that does anything. How long do i need to wait to see the effect of glitch interval setting?

i have some mail for hotmail stuck in the que and this is the msg from Event Viewer, event id 7002

This is an SMTP protocol warning log for virtual server ID 1, connection #648. The remote host "65.54.244.104", responded to the SMTP command "mail" with "421 PR(ct1) The mail server IP connecting to Windows Live Hotmail server has exceeded the connection limit allowed. If you are not an email/network admin please contact your E-mail/Internet Service Provider for help.  For e-mail delivery information, please go to http://postmaster.live.com  ". The full command sent was "MAIL FROM:<aselimanovic@psc.edu.au>  ".  This may cause the connection to fail.

What is cousing that msg to appear? I have sent a msg with attachment (pdf).
Thank you for yo replay as i hvae been stuck with this problem for a while and to hvae someone else to bounce ideas from is great. Thanx again!!
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adnan007Author Commented:
i have started to get greylisted now!!
what can couse this now?

This is an SMTP protocol warning log for virtual server ID 1, connection #663. The remote host "80.252.97.204", responded to the SMTP command "rcpt" with "451-AF-Greylist: Your IP Address 203.173.40.184 (apnic) has been greylisted  451-[http://postmaster.artfiles.de/GL-IA?id=0630-SYoM0aUq9]  451-***************************************************************  451-*  see http://postmaster.artfiles.de/GL-IA?id=0630-SYoM0aUq9  *  451 ***************************************************************  ". The full command sent was "RCPT TO:<cz@fiftyeight.net>  ".  This may cause the connection to fail.

For more information, click http://www.microsoft.com/contentredirect.asp.
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adnan007Author Commented:
i have rad a bit about greylisting and i get it now. interesting thing is though, if i restars IIS all qued msgs get sent with attachments or without!?!
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adnan007Author Commented:
Thank you for all your responses, but my problem is still not solved. As no body is interested in lookin in to it i will close this question.
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