Article ID: 307772 - View products that this article applies to.
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If you select the This server requires a secure connection check box, and then change the port to something other than port 25, you cannot connect to Microsoft Exchange Server or any other e-mail server that requires a STARTTLS negotiation.
There are two different methods to obtain a secure connection for Simple Mail Transfer Protocol (SMTP). The first one works as follows:
The second method is to use a secure socket from the very beginning. Outlook 2000 supports this method on ports other than the default port of 25.
To resolve this behavior, upgrade to Microsoft Outlook 2002; it supports STARTTLS negotiation on ports other than 25.