As you know the SBS 2003 POP Connector in Exchange does not work over SSL. The fix is to download and install STunnel and the OpenSSL binaries. STunnel effectively creates a local POP3 server that will accept non-SSL Â incoming requests from the Exchange Connector and then generate SSL requests to your POP3 server, and then return them back to Exchange.
Exchange is none the wiser, but you have your SSL based POP3 retrievals now working.Â This is my entire stunnel.conf:-
cert = stunnel.pem
options = NO_SSLv2
client = yes
accept = 127.0.0.1:111
connect = pop.outlook.com:995
Note I had to change good old port 110 to port 111 so as not to clash ports. Now just edit your POP Connector configurations to fetch from mailserver 127.0.0.1 on port 111, instead of pop.outlook.com.