exchange 2003 // messages from some domains still on the queues trying to being sen

Posted on 2011-05-08
Last Modified: 2012-05-11
We are having an intermittent problem with our Exchange 2003 server.  Outgoing SMTP messages are forwarded through a smarthost.  Occasionally some messages ( exatly to some domains) are never forwarded and sometimes delayed from 3 to 5 days. It still on the queues trying to being sent

Exchange queues are holding that messages and retry retry retry after some days – at least 3 days - it will go
with this message
Final-Recipient: rfc822;

Action: delayed

Status: 4.4.7

Will-Retry-Until: Sun, 8 May 2011 19:51:30 +0300

As far as I can tell it is random with some domain and when I test Telnet I have no problem send telnet msg

Whenever it happens, message tracking shows:

SMTP: Started Outbound transfer of message
"Message transferred to  through SMTP".
SMTP: Started Outbound transfer of message
"Message transferred to  through SMTP".
And repeat like this 10s of times

Anyone have any ideas?

Also a different problem from one month that if I send email to anybody on the world/ gmail Hotmail/// he will receive my email message on the junk
Question by:Sawyer
    LVL 8

    Expert Comment

    Check if your Smart Host is configured to a proper DNS server which is reachable from Smart Host.
    The DNS server address would normally be of your ISP.
    If you have console access to your Smarthost try to send a mail directly from the Smarthost to that domain.

    Author Comment

    thank you
    yes it was the smart host not configured

    no the problem is solved
    but i have some doubts; before i didnot use smarthost; it was routed by dns and without smtp connector
    we have public ip
    now i created the smtp connector and assign it to the isp smarthost
    everything is ok
    but is this secure?? or it affect something ???
    LVL 8

    Expert Comment

    I feel it is one and the same. Before you were forwarding through Smart Host but now you are directly pointing to the Smart Host.
    But if you want to have a more secure way of handling Inbound and Outbound mail delivery then you need to have some box for external mails and your MX record should be pointing to the box
    some examples are: Ironport for Cisco, Trend Micro

    Author Comment

    can you please give me more detail?
    before i didnot specify a smart host at all / nether in the virtual server & no smtp connector was therr
    actually i have a public ip and the messages was working fine / only one month before this problem came

    please explain me more details about this box and how it works
    many thanks brother;;;
    LVL 8

    Accepted Solution

    If I'm not wrong your MX record is your Public IP which is directly natted /mapped  to your Exchange Front end server which is not a very good practice.

    You can have Relay server preferably configured in the DMZ network. The relay server should be configured with this public IP.
    The Relay server would do the job of Anti-Spam, Antivirus, Sender filtering, Content Filtering and many other stuff at the Gateway level.
    I have provided the links for the best in the market.

    I could also find a freeware you can try this out

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