On Thu, 28 May 2020 19:06:01 -0700 (PDT), Andy wrote:

I use ubuntu, but am curious if this problem occurs with Windows as
well.

I used to be able to send emails to yahoo using a command line.

However, both yahoo and gmail eliminated the ability for LESS SECURE
APPS TO ACCESS EMAIL which stopped ssmtp(allows sending of emails)
from working.


Gmail only considers an app to be "less secure" when the app is
using one's main Google account password.

Was there anything preventing one of these alternatives from being
used ?

(a) Use an "app password" in place of one's main Google account
password when sending mail.
https://support.google.com/accounts/answer/185833
or
(b) Turn on "Less secure app access" in one's Google account
settings.
https://support.google.com/accounts/answer/6010255


2-Step-Verification must be turned on to *create* an app password,
but it can be turned off again afterwards and the app password will
still work.


(ssmtp: Authorization failed (535 5.7.0 (#AUTH005) Too many bad auth
attempts.)

Does that occur when trying to do so from a command prompt in
Windows?


If you were specifically looking for a Windows command line program
which supported OAuth2, then read this thread:
https://alt.comp.os.windows-10.narkive.com/So5sqzzo/oauth2

Otherwise, either (a) or (b) above should work the same in Windows as it
does in Ubuntu.


--
Kind regards
Ralph