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Exchange Server and POP3 outgoing e-mail problems

By techservices123 ·
Hello Everyone:
I have a question regarding POP3 and Exchange Server mail clients. I am the IT guy for a small company that runs SBS 2003 and recently the users have reported problems with their e-mails not reaching their intended recipients. We utilize Outlook 2003 and have it setup for POP3(default) and Exchange server mail clients. Some e-mails do not reach their intended recipients while others go through with no problem. Strangely enough, some users report that the only way they can send an e-mail to a particular domain is by using the "Reply" function and then it will hit the recipient's inbox. Oddly enough, this doesn't occur with all outbound messages, only a select few. Whenever I try to send emails to test accounts like Gmail, Hotmail, Yahoo, the messages always reach their destination.

We have suspected there was a problem with a POP3 host and we have switched companies and made the necessary changes to the incoming/outgoing mail servers within Outlook. Users are able to send messages successfully inside and outside the company. However from time to time they complain that some messages are never sent. These messages look clean on the surface (no attachments, no spam keywords, etc). Most of the time the undelivered messages do not bounce back but a few have come back with the following information: "Your message did not reach some or all of the intended recipients. Could not deliver the message in the time limit specified <company domain #4.47>

I'm not sure why they are using both Pop3 and Exchange server mail clients. The user's mail data file (.pst) is being stored on the exchange server. I was wondering if it would be a good idea to reconfigure the storage of the data file to the local machine and bypassing the exchange server all together and seeing if that makes a difference? Any suggestions?

I am confused as to whether this is an issue with our email and/or the POP3 or exchange server or an issue with the recipient's e-mail. Any assistance would be greatly appreciated. Thanks for your time and consideration.

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All Answers

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Check your external DNS for your email server

by robo_dev In reply to Exchange Server and POP3 ...

Some receiving mail servers do a reverse DNS lookup. If your DNS records have your email server setup as one ip but the firewall as another ip (and the firewall is the one ip the reverse lookup typically looks at). Then reverse lookup fails and mail is dropped.

So you may need to change your firewall ip to be the same as the email server and forward the port to our internal email server ip.

POP3 connector troubleshooting guide
http://support.microsoft.com/kb/885685

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Setup a Smarthost

by tharris1 In reply to Exchange Server and POP3 ...

You may need to route your outgoing mail through another SMTP server, posibly your Internet Provider. Many receiving Email servers will not accept email unknown SMTP servers.

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