Set up Secure POP access for External users SBS 2003 SP2 / Exchange 2003 SP2

Hello Experts,

I need to set up POP access for one External user ot my SBS2003 server. Yes Yes, I know about RPC over HTTP, however; this user mostly uses a satellite internet connection, and we tried RPC over was EXTREMELY I need to set him up for POP access

I successfully set him up to POP to port 995 using a web certificate

and I created a 2nd SMTP virtual server that answers on port 465, the SMTP virtual server is set up essentially th esame as the POP3 virtual server

however, I get the following error in outlook:
"your server does not support the specific type of encryption you specified"

when I telnet to on port 465...i successfully connect

any ideas?
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Tom-J-LaelConnect With a Mentor Author Commented:
Fixed it. on a whim I went to  the SMTP virtual server using port 465. I went to Delivery tab>Advanced> and entered "localhost" as a smart host

can anyone tell me why email wouldn't go out otherwise??
Tom-J-LaelAuthor Commented:
Figured it out:

IN Outlook2007 selected us TLS instead of SSL
Tom-J-LaelAuthor Commented:
Ok. New issue. Emails will only go to recipients on my internal exchange server. Emails outside of the internal Exchange server do not go anywhere.
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Olaf De CeusterCommented:
Hi Tom,
Why didn't you just use the pop3 server in SBS?
In services setup POP3 to start autoaitically, run the internetconnection wizard and in the firewall section add POP3 for whatever port. Done.
Tom-J-LaelAuthor Commented:

I am using the POP3 server in SBS.

I wanted to set up a seperate SMTP server for the external user to use, so I could require secure connections using TLS
Olaf De CeusterCommented:
Closed, 500 points refunded.
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