I would like to configure Exim to send all of my non-local outgoing mail 
through an external relay on port 465. The relay host requires TLS and 
SMTP authentication. I do not need to use TLS for incoming mail.

I am confused as to whether I need to set up a private key and certificate 
to send outgoing mail (I would assume that I don't need a certificate, 
because I can send mail from my mail client via the same relay host 
without signing a certificate!).

Currently I have the following in my exim configuration file (edited for 
anonymity):

  Under "routers":

    send_through_myrelay: 
      driver = manualroute 
      route_list = !+local_domains smtp.myrelay.com 
      transport = myrelay_smtp

  Under "transports":

    myrelay_smtp: 
      driver = smtp 
      user = exim 
      hosts = smtp.myrelay.com 
      hosts_require_auth = smtp.myrelay.com 
      hosts_require_tls = smtp.myrelay.com
      port = 465

  Under "authenticators":

    myrelay_login: 
      driver = plaintext 
      public_name = LOGIN 
      client_send = : myname : ******

If I try to send mail with this configuration as it stands, I get the 
following in my verbose output from exim:

  Connecting to smtp.myrelay.com [111.222.333.444]:465 ... connected
  waiting for data on socket
  selecting on subprocess pipes
  selecting on subprocess pipes
  selecting on subprocess pipes
  selecting on subprocess pipes
  selecting on subprocess pipes
  ok=0 send_quit=0 send_rset=1 continue_more=0 yield=1 first_address is 
  not NULL LOG: MAIN
  SMTP timeout while connected to smtp.myrelay.com [111.222.333.444] after 
  initial connection: Connection timed out

What should I do to get my TLS and authentication working?

thanks,
Matthew.

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