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Exchange Server 2003 will not send to certian domains (ex.hotmail.com) after migration from exhange 5.5

Posted on 2004-09-16
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Last Modified: 2012-05-05
I'm using Exchange 2003 Server on a Windows 2003 server Domain.  I recently migrated from Windows NT 4 and Exchnage 5.5.  Everything went ok, but now i can't send to certian domains, they keep comming back delayed, then undeliverable.  I have tried alot of things, but maybe i missed something.
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Question by:lecci
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by:ColinRoyds
ID: 12076101
If it all used to work then my guess would be that your DNS name out on the www is not the same as your real server name so....
Open ESM go to Default SMTP virtual server / properties / delivery / advanced / and under masquerade domain type the same name in as what your DNS is set to on your MX records.

Example:
MX record mail.domain.com
Real name server.domain.com
add MX name in to where the masquerad entry is, then the mail headers will match and all mail sent out will look like it came from mail.domain.com which is what your MX records state.

AOL and Hotmail are sticky about this.

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by:Sembee
ID: 12076127
When the emails bounce back - what is the exact error message for the failure?

For a fast solution you might want to try an SMTP Connector pointing at your ISPs mail server, then add the domains you are having problems with to the connector.
http://www.amset.info/exchange/smtp-connector.asp

Simon.


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Author Comment

by:lecci
ID: 12076595
This is the first message i get:

This is an automatically generated Delivery Status Notification.

THIS IS A WARNING MESSAGE ONLY.

YOU DO NOT NEED TO RESEND YOUR MESSAGE.

Delivery to the following recipients has been delayed.

       sjc_design@hotmail.com

After that i get a message saying that it wasn't able to send to it.
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Author Comment

by:lecci
ID: 12077267
Here's another issue with Sembee's answer....Our ISP's SMTP requires authentication...so it just comes back relaying denied..

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Author Comment

by:lecci
ID: 12077814
yeah, and i tried ColinRoyds's answer and no diff. unless i have DNS set up wrong or something...but it just sits in que
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Expert Comment

by:ColinRoyds
ID: 12077922
I would now start using nslookup on the troublesome domains find the MX record and try telnet into the mail server on port 25
telnet server.domain.com 25

try sending a mail using manual smtp commands through telnet and see if it accepts them.

If you can't resolve these addresses you might want to try add a forwarder in your DNS so that it uses your ISP's DNS for resolution and see if this makes a difference,
you might want to try these and post the results here including any errors you might get

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Expert Comment

by:ColinRoyds
ID: 12077937
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Author Comment

by:lecci
ID: 12078387
220 mc9-f15.hotmail.com Microsoft ESMTP MAIL Service, Version: 5.0.2195.6824 rea
dy at  Thu, 16 Sep 2004 12:23:53 -0700
HELO mc9-f15.hotmail.com
250 mc9-f15.hotmail.com Hello [207.68.114.35]
MAIL FROM:scourson@bettsind.com
250 scourson@bettsind.com....Sender OK
RCPT TO:jeffreygsnyder@hotmail.com
250 jeffreygsnyder@hotmail.com
DATA
354 Start mail input; end with <CRLF>.<CRLF>
SUBJECT:Testing2

This is a test message.
.
250 <MC9-F15Wud6oFbCy5BK0007dd09@mc9-f15.hotmail.com> Queued mail for delivery


that from the exchange server to hotmail
i dont know if that's the right response i should get or not, but that's what i got
i telneted into mail.hotmail.com 25

what do you think?

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Expert Comment

by:ColinRoyds
ID: 12078409
that all looks good, if there was a problem it would have kicked you out half way through.
so from that I cannot see a problem at all
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Expert Comment

by:ColinRoyds
ID: 12078430
the only other thing now is to enable SMTP logging send a test mail to a problem domain and once again post the output here.

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Author Comment

by:lecci
ID: 12078578
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Expert Comment

by:ColinRoyds
ID: 12078673
your best bet is to enable loggin , this will give a more detailed log of the entire smtp conversation between the mail servers, unfortunately the screenshot just confirms the issue but doesn't help find the problem. good try though
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Author Comment

by:lecci
ID: 12078749
Event ID: 7004

This is an SMTP protocol error log for virtual server ID 1, connection #1302. The remote host "206.46.170.8", responded to the SMTP command "rcpt" with "550 relaying mail to hotmail.com is not allowed  ". The full command sent was "RCPT TO:<digitaldj02@hotmail.com>  ".  This will probably cause the connection to fail.
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Author Comment

by:lecci
ID: 12078947
Ignore that last message....here's one thing though, the message goes into queue and sits there, but nothing is logged on why?...is  there a log i'm not turing on.

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Expert Comment

by:ColinRoyds
ID: 12078954
It could be a few things
1. Make certain you are not an open relay (probably not the cause but still worth checking)
2. check if you have a valid "PTR" record (revers DNS) here is AOL reverse DNS checker http://postmaster.aol.com/tools/rdns.html
3. Back to what I mentioned in the beginning, make certain your DNS MX record and real server name match, correct if neccessary by using masquearding on the defauly SMTP virtual server.
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Expert Comment

by:ColinRoyds
ID: 12079012
You might also want to try turn on loggin for all under MS Exchange Transport
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by:ColinRoyds
ID: 12079046
By the way, slightly different way of thinking, but check your firewall, do you have a rule for outbound SMTP that is a "SMTP proxy service", I have seen Watchguard firewalls do this. they proxy the SMTP conversation but do not support all the SMTP commands and everything falls to pieces.

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Author Comment

by:lecci
ID: 12079145
my reverse DNS is comming up as....


dpvc-207-68-114-35.alt.east.verizon.net


shouldn't it be comming up as mail.bettsind.com


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ColinRoyds earned 500 total points
ID: 12079229
I think that should be fine, as long as it is not something like in.addr.arpa which is not accepted, and no mail.bettsind.com is different that is a lookup against your MX records, a revers DNS lookup is ip against domain, which is looked after by the ISP who allocated you your IP not the ISP holding the domain zone.
bit confuzzing I know.
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