Re^2: Problem sending Gmail from Widows 10

Unfortunately, the advice of all three people didn't help. Curiously, if I change the case from -layer=> 'tls', to -layer=> 'TLS', then the error messages change entirely:

  ...
  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.

Comment on Re^2: Problem sending Gmail from Widows 10 Download Code

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Re^3: Problem sending Gmail from Widows 10 by afoken (Chancellor) on Nov 14, 2015 at 18:29 UTC
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". ;-)	[reply] [d/l] [select]

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Re^3: Problem sending Gmail from Widows 10
by afoken (Chancellor) on Nov 14, 2015 at 18:29 UTC

  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". ;-)

[reply]
[d/l]
[select]