[UFO Chicago] How Do You Configure Sendmail To Relay Outgoing Mail Thru An Encrypted Connection?

[Neil R. Ormos]

Jay F Shachter wrote:

> Here is a verbatim transcript of an hourlong chat I had with my ATT
> technical service representative.  I hope it will be more amusing for
> you to read it than it was for me to participate in it.  And if you
> can answer the question that Zachary could not even comprehend, I
> shall be much obliged. [...]

Does this blog post help? 

|> Configure sendmail as a client for SMTPs

|> Overview 

|> The motivation to configure sendmail as a
|> client for Simple Mail Transfer Protocol with
|> SSL (SMTPS) came about when I switched ISP's
|> and the new service required authentication as
|> well as the use of port 465 to submit an email
|> for delivery. In my case the ISP was AT&T
|> U-verse powered by Yahoo! Mail. The old ISP
|> permitted the use of port 25 as long as your IP
|> address was part of their network, whereas the
|> new service blocks that port to outgoing
|> traffic. Setting up SMTPS is fairly easy to do
|> using a client like Evolution, however, it is
|> not quite as straightforward to configure
|> sendmail to do the job. The reason why I needed
|> sendmail was to allow my home server to send
|> email using the PHP mail function from a web
|> page. One of the uses of this server is as a
|> platform for website development and testing. I
|> will also show how it is possible to receive
|> email on your home server using a dynamic dns
|> provider. [...]

  <https://fedoraproject.org/wiki/Configure_sendmail_as_a_client_for_SMTPs>

--Neil Ormos