qmail -> Exchange

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    I believe I mis-posted this as a reply to another thread in the outlook forum.

    I’ve got Exchange 2003 on SBS 2003. However, I’m having some problems. I was able to send mail internally through any account on our qmail server to some test mailboxes I had set up in exchange. I just created several users (test1, test2 etc) in AD, mail enabled them and set up my outlook to check those mailboxes as well as my main one. All seemed to be running fine except… OWA wasn’t working. Some tweaking in IIS fixed that. Now I can log into OWA and I must admit, from the perspective of someone who’s used pretty much every iteration of the outlook web client this is pretty slick.

    But now I can’t send mail anymore. If I log in to OWA and attempt to send to my main email address (on the qmail server), it just gets delayed until the server reaches it’s timeout and then it’s deemed undeliverable.

    When I try to send through Outlook from my main address to any of the test addresses, qmail gives me:

    > Connected to but sender was rejected.
    > Remote host said: 530 5.7.0 Must issue a STARTTLS command first

    the exchange server seems to be rejecting it b/c qmail doesn’t issue starttls. so turned off tls everywhere I thought I could but I’m still getting the failure notices. OWA still works so I know I haven’t broken any necessary SSL settings. But I’m assuming something in the SSL dept. is misconfigured if I’m getting these errors.

    I’d like to get my functionality back so I can continue my testing. Sorry for the cross-post but it’s been several days w/o a reply and I realized it was in the wrong forum before anyway.

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