Net::SMTPS=GLOB(...etc...)>>>> EHLO localhost.localdomain
  Net::SMTPS=GLOB(...etc...)>>>> 250-smtp.gmail.com at your service ..
+.
  Net::SMTPS=GLOB(...etc...)>>>> 250-SIZE 35882577
  Net::SMTPS=GLOB(...etc...)>>>> 250-8BITMIME
  Net::SMTPS=GLOB(...etc...)>>>> 250-STARTTLS
  Net::SMTPS=GLOB(...etc...)>>>> 250-ENHANCEDSTATUSCODES
  Net::SMTPS=GLOB(...etc...)>>>> 250-PIPELINING
  Net::SMTPS=GLOB(...etc...)>>>> 250-CHUNKING
  Net::SMTPS=GLOB(...etc...)>>>> 250 SMTPUTF8
  Net::SMTPS=GLOB(...etc...)>>>> AUTH LOGIN
  Net::SMTPS=GLOB(...etc...)>>>> 530 5.7.0 Must issue a STARTTLS comma
+nd first ... Authentication (SMTP) failed

[download]

but note that one of the messages confirmed STARTTLS already.

Are you sure? I only see an SMTP server identifying as smtp.gmail.com announcing its capabilities conforming to RFC1869, which are 8 bit MIME messages, TLS encrypted communication, enhanced status codes, and so on. I don't see any TLS confirmation here. RFC2487 documents that the EHLO command needs to be followed by a STARTTLS command. Your output shows AUTH LOGIN instead.

Alexander

--
Today I will gladly share my knowledge and experience, for there are no sweeter words than "I told you so". ;-)

In reply to Re^3: Problem sending Gmail from Widows 10 by afoken
in thread Problem sending Gmail from Widows 10 by haprst

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.