Question : External Email SMTP problem

This is my setup:

1 Front-End Exchange 2003 Server
2 x Backend Exchange 2003 Cluster

on Front-End I have 2 SMTP Servers, Default_SMTP and Secure_SMTP

Default_SMTP is running on port 25
Secure_SMTP is running on port 2525 and uses ssl certificate

on Backend-cluster I have 1 Virtual SMTP Server running normal port 25

I have 2 SMTP Routing connectors:
   Connector1 -  uses Default_SMTP as bridgehead, SMTP * cost 1, defaults
   Connector2 - uses Secure_SMTP as bridgehead, SMTP * cost 1, outbound security uses TLS encryption


When using normal Outlook exchange mode, it basically uses Default_SMTP and email is properly sen1 and received to internal and external addresses with no problem.

When setting up Outlook with IMAP, setting SMTP to use SSL and port 2525, when sending external emails,they are getting stuck in the Secure_SMTP Queue and get error"The remote SMTP service does not support TLS", when sending emails to internal users, it works fine!


What am I doing wrong? how can I make this work properly so users using my Secure_SMTP server listening on port 2525 are able to send emails to external addresses with no problems?

Answer : External Email SMTP problem

You can't assign a virtual smtp server to a connector.  You have to control connector routing via the address space and cost as I described above.  

To fix this immediate issue, try setting up another Secure_SMTP virtual server on your backend cluster and test from there.