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Changed my ISP, now outgoing mail is delayed in Exchange 2007.

Posted on 2011-10-29
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Last Modified: 2012-05-12
I changed my ISP and thus my static IP is different.  I am using SBS 2008 with Exchange 2007 SP3.  Some mail is getting hung up in the queue and never getting delivered.  The error displayed is 451 4.4.0.  I've tried telnet to send a message and get error 550 5.7.1 Unable to relay.

I still have my old ISP and if I reconnect them to my router and change my IP info back to the IP they gave me mail goes out no problem.  I've changed my dns to opendns so it doesn't appear to be an issue there.  And it only happens on some mail I send...not all.

Any help would be greatly appreciated.
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Question by:tgustaf
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LVL 21

Expert Comment

by:Papertrip
ID: 37050919
Create a PTR record in DNS for the new IP that points to the A record of your outgoing mail server.

If you have have an SPF record for your sending domain(s), then you need to add the new IP to it.
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Expert Comment

by:Papertrip
ID: 37050930
I should add that, while that may not completely resolve the issue, they are things that should be done regardless.
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LVL 15

Expert Comment

by:.
ID: 37050946
Are you using a smarthost?

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Author Comment

by:tgustaf
ID: 37050968
I did add the PTR and SPF records already.  No I'm not using a smart host.
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Expert Comment

by:celazkon
ID: 37051297
Could be because of the reverse DNS check performed on the receiving mailservers, that you have problem to send mail to. Ask your new ISP to create a reverse DNS record and set it up according to the FQDN value on your exchange send connector (Exchange management console - organization configuration - hub transport - send connectors tab - connector's properties general tab) for the new public IP address.
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Expert Comment

by:.
ID: 37052098
Do a multi RBL check on your new IP
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Author Comment

by:tgustaf
ID: 37053121
No blacklists, or brownlists.  One yellow list. No whitelists, 15 neutrallisted.
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Author Comment

by:tgustaf
ID: 37053163
Some more details that may help.

I have three domains.

mydomain.com
mydomain.biz
my2nddomain.com

mydomain.com is the one that I use... the other two I have set up on exchange as authorative domains.

Back before I had a server I had my2nddomain.com which was my website and email hosted off site.  I then decided I didn't like the domain name so I changed it to mydomain.com... also hosted off site.

mydomain.biz was the original domain I set up when I set up my server.... which I only used to access remote web workplace via remote.mydomain.biz

Exchange was originally configured with remote.mydomain.biz as the send connector... even though I wasn't using it for my mail.

Later I decided I wanted to host my mail in my exchange, so I added the other domains to the Accepted Domains list and set mydomain.com as the default.  My FQDN of my send connector is still remote.mydomain.biz  which is also where I have the SSL certificate registerd with.

I have my mailbox set up with email addresses at the mydomain.com, mydomain.biz and my2nddomain.com, but the mydomain.com is the one I use as default and the only one I use for outgoing mail.

Again... everything works with my original ISP, but when I switch to my new ISP I get delayed messages which eventually fail as non-deliverable.

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Accepted Solution

by:
tgustaf earned 0 total points
ID: 37053599
Hmmm... appears to have been some issue with my ISP.  I asked him to verify that port 25 outgoing was open and after a few messages back and forth things started working.

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Author Closing Comment

by:tgustaf
ID: 37081714
Thanks for everyone's help.
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