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Delivery to the following recipients has been delayed

Posted on 2009-04-10
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Last Modified: 2012-05-06
Client of mine called this morning saying they are having issues sending out mail.  I log into one of the workstations and saw "delivery to the following recipients has been delayed"

I log into the server (SBS2003) with a bunch of Small Business SMTP Connectors just sitting in the queue.  

If I do a nslookup of the domain it resolves the MX Records.  I went to Default SMTP Virtual Server and added the ISP DNS servers under Advanced.  Didn't fix anything.  

If I right click on Small Business SMTP Connector and send mail out through Smart Host (using mail.optonline.net which is our ISP mail server) and not through Direct Send it works.  

But I have alot of my clients using Direct Send and it all works fine.  So any idea on what I can do?
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Question by:Fluid_Imagery
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by:Mestha
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It could be that your ISP has blocked port 25, or that the server is on a blacklist. If you can end email through the SMTP server belonging to the ISP then it isn't a problem with the server.

Can you telnet to port 25 of any remote email server?

Simon.
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by:Fluid_Imagery
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How can I test the telnet?  Which email server should I try?  

Port 25 can't be blocked since I can send mail through mail.optonline.net correct?

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by:shahsejal
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Instead of to adding the ISP DNS servers under Advanced on the Default SMTP Virtual Server please try adding a Public DNS server 4.2.2.2 and compare the results.
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by:Fluid_Imagery
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Same problem.  

Changed back to mail.optonline.net and it sends right out.  Other way gets locked in queue.  

I am on Postini and I believe they let you have an Outbound SMTP that I can use just wondering why this happened out of the blue?
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by:Mestha
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The fact that you can telnet to your ISPs SMTP server just means that the port is open inside the ISPs network. You need to attempt to connect to a remote server.

telnet maila.microsoft.com 25

If you cannot to that server then the port is being blocked and you will need to ask your ISP why.

Simon.
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by:Fluid_Imagery
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C:\Documents and Settings\dan>telnet maila.microsoft.com 25
Connecting To maila.microsoft.com...Could not open connection to the host, on port 25: Connect failed

same thing on my work computer and that server.  
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by:shahsejal
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So you would be able to telnet "mail.optonline.net " on port 25. BUt could you telnet to your Firewall on port 25?
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Mestha earned 500 total points
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That means your ISP is blocking port 25. You will need to call them and find out why.

Simon.
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by:Fluid_Imagery
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I called them after I posted, for some reason the Static IP service wasn't linked to the modem anymore......lol

so Boost and Static IP wasn't on the account, ports weren't open.  I had him change it, but of course the machines didn't come back online so I gotta go there on Monday to restart the network devices.
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Author Closing Comment

by:Fluid_Imagery
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ISP issue.  Resolved.
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