Problem with outgoing mail on Exchange 2003

Posted on 2007-10-10
Last Modified: 2012-05-05
We are running Exchange Server 2003 Enterprise SP2 on Windows 2003 server SP1. We have a single site with a single domain and approx 70 users. Our ISP is demon internet and our server is configured to receive email via SMTP and to send using the demon smarthost (

Today we have had big problems with outgoing email. (no problems with incoming however). When I track meesages they seem to be stuck at the "message routed and queued for remote delivery stage" and then all of a sudden they all seem to go at once. The longest delay I have seen has been about 1 hour.

One other thing I have noticed....

When the message finally goes, i see the following entry in the tracking option.

SMTP: Started outbound transfer of message
Message transferred to    through SMTP
SMTP: Started outbound transfer of message
Message transferred to    through SMTP
SMTP: Started outbound transfer of message
Message transferred to through SMTP

As you can see, in the first 2 entries it seems like it can't find where to send the message.

Can anybody shed any light on this? I have contacted Demon and they say they don't have any problems but I have very little faith left in their technical support. If it isn't Demon's fault, then can anyone suggest anything I should check on my server??

Question by:metamatic
    LVL 6

    Accepted Solution

    It sounds like an issue with Demon as your SMTP forwarder. But if not here are a few things to look at.

    If your email is queueing on your server it must not be connecting to your smtp forwarder at times for some reason.  When it is queued up I would try pinging the host to see if it is up or you can route to it properly. Then verify if your exchange server is using DNS forwarders in exchange system manager and if you need to change them or leave it blank and let your DNS server resolve to the outside network. Then if you are not using forwarders in exchange I would see what forwarders you are using in AD DNS. I have seen a lot of problems where 1 external DNS server was not acting right and changing it or removing it would fix issues with exchange routing or accessing certain web sites.

    I have never used an SMTP forwarder personally but I would imagine that reverse lookup issues or blacklisting would not be a factor here.

    Thats off the top of my head let me know if it helps.
    LVL 5

    Expert Comment

    You could use a tool such as PORTQRY to verify that if you can resolve the smarthost that it is actually listening on the configured SMTP port.
    LVL 104

    Expert Comment

    Demon's smart hosts are crap. Any reason you are using them? I have more problems with Demon internet and their mail service than anyone else after BT.

    Demon use a cluster, so there is a good chance that one of the servers in the cluster has failed. Be lucky it was just an hour, I have seen emails disappear in to those clusters for six weeks.


    If your question has been answered, pleased remember to accept the answer and close the question.

    Author Comment

    It does indeed look like a demon issue. I had a MS support call that was due to expire so I got them to dial in to our exchange server and they couldn't find anything wrong at our side. This issue (and the way demon support have handled it) have finally made up my mind and will be signing up with a new provider this week.

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