Exchange 2007 not recieving mails but get stuck on SBS 2003 after Migrate

Posted on 2011-04-23
Last Modified: 2012-08-14
I have followed all the instructions from Microsoft to migrate from SBS 2003 to SBS 2008. Unfortunately I cannot get messages to be delivered to sbs 2008 and therefore i have hundreds of emails in queue.

I have removed the connectors, configured hub transport, i can telnet to port 25 successfully, is there something that i might be doing wrong?

When I run the troubleshooting assistant I get Mail submission failed: Error message: Server does not support secure connections. I have installed a new self assigned certificate with no success.

I can send emails, but weird thing is that they end up getting into the junk, spam folder of the recipients
Question by:Jkipkangor
    LVL 9

    Assisted Solution

    Please be more specific about where you are in the migration process.  Is the SBS 2003 server removed from the domain?  What queue is mail getting stuck in?  You're saying that you're having trouble receiving mail - which means the queue you are refernecing would be the sending server's queue, right?  

    "I can send emails, but weird thing is that they end up getting into the junk, spam folder of the recipients"

    I doubt that's the case for 100% of emails.  That may be a server configuration issue - you're on a blacklist or you need a reverse DNS record or something else.
    LVL 3

    Accepted Solution

    are you using smarthost  to send mail from the sbs2003 ?

    Assisted Solution

    Had moved the mailboxes and the mails were stuck in the old sbs 2003, I haven't removed the old one from the network.
    It turned out that smart hosts field had smtp.<myisp>.com and when I removed it, it worked! No sent mails going to junk/spam folders.
    One question, when removing sbs 2003 from the network, are there any other configurations to be done?

    Author Closing Comment

    First in the checklist should be smarthosts next time I am migrating/installing exchange.

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