Don't bother starting to automate with Perl (Email::Sender is super sweet) until you can get a successful SMTP session manually. This decade's best practice: encryption, authentication, submission port. Try variations of this: 
$ echo '\000mysmtpusername\000mysmtppassword' | openssl base64
XDAwMG15c210cHVzZXJuYW1lXDAwMG15c210cHBhc3N3b3JkCg==

$ # ↑↑↑↑ copy this to clipboard

$ openssl s_client -connect mailhost.faraway.example.net:587 -starttls smtp

ehlo hostname.here.example.org
auth login XDAwMG15c210cHVzZXJuYW1lXDAwMG15c210cHBhc3N3b3JkCg==
and you know the rest: 
mail from: <samwyse@host.here.example.org>
rcpt to: <fnord@example.com>
data
⋮

In reply to Re: Net::SMTP in the 21st Century by daxim
in thread Net::SMTP in the 21st Century by samwyse

Title:
Use:  <p> text here (a paragraph) </p>
and:  <code> code here </code>
to format your post, it's "PerlMonks-approved HTML":


  • Posts are HTML formatted. Put <p> </p> tags around your paragraphs. Put <code> </code> tags around your code and data!
  • Titles consisting of a single word are discouraged, and in most cases are disallowed outright.
  • Read Where should I post X? if you're not absolutely sure you're posting in the right place.
  • Please read these before you post! —
  • Posts may use any of the Perl Monks Approved HTML tags:
    a, abbr, b, big, blockquote, br, caption, center, col, colgroup, dd, del, details, div, dl, dt, em, font, h1, h2, h3, h4, h5, h6, hr, i, ins, li, ol, p, pre, readmore, small, span, spoiler, strike, strong, sub, summary, sup, table, tbody, td, tfoot, th, thead, tr, tt, u, ul, wbr
  • You may need to use entities for some characters, as follows. (Exception: Within code tags, you can put the characters literally.)
            For:     Use:
    & &amp;
    < &lt;
    > &gt;
    [ &#91;
    ] &#93;
  • Link using PerlMonks shortcuts! What shortcuts can I use for linking?
  • See Writeup Formatting Tips and other pages linked from there for more info.