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SBS2008 Mail

Posted on 2013-12-12
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Last Modified: 2013-12-16
Hi,

We have a SBS2008 server that has been working fine. We just moved to a new ISP and MX records were change.

We have users who can receive mail but cannot send. Mail sits in the que. I reran the internet connection wizard and can't get things working. Any help would be great.
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Question by:blackbear67
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Expert Comment

by:tsaico
ID: 39715893
I would look at your return PTR and also what is in your SPF records.  Check out www.mxtoolbox.com for an external site to check things out.  put in your hostname, when it returns results, choose the SMTP test.  While you are there, I would also check the blacklist in case your new IP was already black listed before it became yours.  

In  many cases, if your PTR does not match your banner, then it will increase your Spam score or you might get rejected entirely.  This will be particularly true if there is a SPF entry that reflects old information, or if you are on a blacklist.
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ronnypot earned 500 total points
ID: 39716038
Hi,

Please check if your send connector in Exchange 2010 management console is nog configured to use a smarthost and there is a smart host configured from your old ISP.

Also check if your new ISP is not blocking port 25 some ISP's block port 25 and you have to send email via there smart host.

Last go to the Queue viewer in the exchange management console toolbox and in the view scroll to the most right there should be a comment why the emails are stuck in the queue.
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Author Comment

by:blackbear67
ID: 39716081
The reverse DNS is ok no issues with MXtoolbox.

We did not previously use a smart host so none was configured. I will send an email (since we send out fine) and ask the new ISP if they are blocking 25. you may be on to something with the smart host. the error is 451 4.4 primary target IP address responded with 421 4.21 unable to connect to  attempt fail over to alternate host but did not succeed. either there are no alternate hosts or delivery failed to all alternate.
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Expert Comment

by:Simon Butler (Sembee)
ID: 39716103
The error you have posted means the server is unable to connect to the remote server. You have said that two users are unable to send. Is that tending to ANY recipient, or just unable to send to specific domains? It is very important because it indicates where the problem is.

If it is to specific domains then it could be a connectivity issue.

Simon.
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Expert Comment

by:Bing CISM / CISSP
ID: 39716590
just public IP address and the corresponding DNS/MX records have been changed?

is the SBS2K8 sitting behind a firewall on a private address or directly having the public IP?
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Expert Comment

by:tsaico
ID: 39720831
You can also try switching the Send connector to use DNS instead of a smarthost for a little bit.  Write that setting down if there is something in there, when you change it, it will not retain what value was in there.
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Author Closing Comment

by:blackbear67
ID: 39721162
It was the new ISP blocking port 25.
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