Employee mails from home, personal email account not being recieved by reciepients at the office

Posted on 2007-08-07
Last Modified: 2010-03-06
One of our guys at the office has set up his email at home using pop3 through his ISP and Outlook as his client.  Here is the problem.  If he sends an email to anyone here at the office from home it is not recieved.  Furthermore, there is no NDR generated.  He seems to be able to send mail to other domains without issue.

We use SBS 2003 here at the office and have had 0 complaints about email not being recieved by anyone else.  Everything is running swimmingly near as I can tell.  I used the message tracking feature in Exchange's System Manager and can not find the emails he is sending, he tried last night at 9:01 for instance, no record.  I can only surmise from this that they are not being recieved by our server at all.

As an experiment I logged on (from the office) I logged on using his credentials to his ISP's webmail client and sent test mails successfully.  Further, I set up a second email account in Outlook on my end (at the office) to use his ISP's POP3/SMTP server, just the same as he has it configured at home.  I was able to both send and recieve mail in this fashion, including mail to our domain.

So I am stumped, any ideas?
Question by:xfungalx
    LVL 10

    Expert Comment

    hi there, its obviously not a problem with his email account and more a problem with the setup on his pc at home. Most likely he has some anti virus or security software that is running a firewall and is blocking SMTP mail to your domain. Disable all anti virus and firewall software first.
    Also, try to Telnet to your server from his home pc and see if it allows connection as this could be an indicator of firewall blocking if you cannot connect.

     From his outlook client at home, you can run a 'test settings' from the POP account setup and see if the outlook client can connect sucessfully to both the incoming and outgoing servers. Check also to see if the mails are building up in his outbox at home, this could also indicate that there is a problem with the 'outgoing server' setting on his outlook client and he may need to check with his ISP to confirm that he is using their recommended one.

    Author Comment

    I have already instructed him to try with his anti-virus disabled tonight.  I didn't think about telnet though, good idea.

    "Test Settings" works from home he says.  He has been on the phone with his ISP's tech support and run through that part.  They suspect it is a problem with our server.  I just can't find any evidence of that on my end.

    Author Comment

    Telnet was successfull with a/v enabled and disabled.  Test messages do not work either way.  Still stumped on this.  
    LVL 10

    Expert Comment

    just in case its a configuration issue with his email client, have you tried setting up a pop account for him on his home pc using another email client such as Outlook Express? If the mail sent through this, then it has to be something to do with the outlook configuration. Also, try and see if his IP address at home has been blacklisted for spam/relaying as this could be causing a problem sending to certain domains. You should be able to do a spam database lookup from the website below:
    If his ip address is flagged for problems, then you should see this here fairly obviously. You can then speak to his ISP and see if they can do anything.

    Author Comment

    After putting this on the backburner for a long time I decided to jump on it again.  The problem is resolved.  The company that hosts our DNS also at one time hosted our mail via pop boxes.  When I dropped that service and went to hosting our own email they didn't drop fix all the pointers on their end and messages from their network to ours were being sent to their server.  This was especially tough because before I posted this question I spoke with their tech support to make sure this very problem was not an issue.  I was assured it wasn't on their end.  I started testing again today and demonstrably showed that SMTP messages from them were NOT reaching our server, nothing, nada, zip.  I called them again today and lo and behold this tech saw the problem and corrected it.  

    Thanks to all who helped out, all valid avenues to explore...
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