I have a few clients (including myself) that use OLK/Express however, I have not been able to get reliable outbound connectivity to work.

We are using 993 SSL on IMAP & 587 SSL on SMTP.

We consistently see this type of error message:

The message could not be sent. The authentication setting might not be correct for your outgoing e-mail [SMTP] server. For help solving this problem, go to Help, search for "Troubleshoot Windows Mail", and read the "I'm having problems sending e-mail" section. If you need help determining the proper server settings, please contact your e-mail service provider.

The rejected e-mail address was 'JSMITH@XXX.com'. Subject '', Account: 'mail.XXX.com', Server: 'mail.XXX.com', Protocol: SMTP, Server Response: '530 5.7.0 Must issue a STARTTLS command first', Port: 587, Secure(SSL): Yes, Server Error: 530, Error Number: 0x800CCC79

Subject 'Re: check', Account: 'mail.XXX.com', Server: 'mail.XXX.com', Protocol: SMTP, Server Response: '530 5.7.0 Must issue a STARTTLS command first', Port: 587, Secure(SSL): Yes, Server Error: 530, Error Number: 0x800CCC7C


I was able to do a test message successfuly to internal address with SMTP set to 25 w/out SSL, but to @gmail, it says it sent, but it never shows up.

I go back and set the SMTP port to 587 w/ SSL, and then I get this error message:


Task 'mail.XXX.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).'


I know these port settings are correct and work, as we are using PC clients w/ Thunderbird successfuly with this, and all of our mac clients use apple mail or entourage with these settings -- only OLK/OLK Express fails each time on outbound mail.

anyone seen this already?