Hi,

I have an Exchange 2013 server for my small Company. One server for everyone. I have a send connector configured to forward outgoing e/mails to an ISP. Everything has been working very well but now I changed ISP. The new ISP has configured their server for me using basic authentication and SSL/TLS enabled over port 465.

I have changed port to 465 using set-sendconnector command.

The ISP has created the smarthost server only for me and it has its own self generated certificate and I have received the serial number for the certificate.

I don't know what to do with the serial number so I did nothing.

Now when I try to send mail it gets stuck in the queue with error 4.4.1 and 4.4.2. I assume its because of issues with the smarthost certificate.

Any suggestion how I should handle this situation?

Thanks!

Hi 

For the Certificate :-
Since your ISP requested the SSL they issued the CSR, so have them install the SSL and export it to a .pfx, password protected file and send you both, the .pfx file and then the password, so you can revoke your current certificate and successfully import it on your end. If they won't do it, cancel the request and issue your own CSR and purchase the SSL on your own from Digicert who gives to amazing service.

For the mails :-

Please make sure that you have changed your smart host from old ISP to the new ISP.

Try to do a Telnet on port 465  from your network to your new ISP and see if you get a response