Question : Exchange server 2007

I've got a bit of a problem here. I've set up Exchagne 2007 and most everything is working properly. However, the client demanded POP/SMTP access to the mailbox. Any ideas on how to resolve the problem? I can't send email (but can recieve using POP w/SSL on port 995). Trying to send w/SSL on port 587. The following are all examples of my problem with different client settings. SMTP Authentication is enabled (use same settings as incoming mail server). Client is Outlook 2003.

If using SMTP port 587, with SSL, get error:
530 5.7.1 Client was not authenticated
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If using SMTP port 25, with SSL, get error:
Task 'mail.domain.com - Sending' reported error (0x800CCC7D) : 'Your outgoing (SMTP) server does not support SSL-secured connections. If SSL-secured connections have worked in the past, contact your server administrator or Internet service provider (ISP).'
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If using SMTP port 25, with NO SSL, get bounceback email:

Your message did not reach some or all of the intended recipients.

      Subject:      test
      Sent:      1/13/2009 12:33 PM

The following recipient(s) could not be reached:

      '[email protected]' on 1/13/2009 12:33 PM
            550 5.7.1 Unable to relay

Answer : Exchange server 2007

That means you are using a self generated certificate.
SMTP may have a problem with it because it is not a certificate that can be verified - either on the trust or the server name. I can't remember if the certificate trust is that strict because I always deploy my servers with trusted SSL certificates.

-M