Michael wrote:

On Thursday 26 September 2024 11:44:08 BST Dale wrote:

Michael wrote:

On Thursday 26 September 2024 08:28:47 BST Dale wrote:

ssmtp stopped working with a conventional password when Google
introduced 2-

Step-Verification for their GMail account.  Consequently, to be able to
continue using ssmtp you need to set up an 'App Password' and use the 16-

character password generated by Google to login:
 https://support.google.com/mail/answer/185833

It used to be the case you could set up an 'App Password' without having
to
provide them with your phone number and other 'none-of-their-business'
personal information, but for some years now they have been asking for
more
information to allow you to complete setting up 'App Password' for your
Google account(s) and device(s).

I also tried the 16 character password method too.  It still didn't work.

In this case the ssmtp package has outlived its usefulness.  It was always 
limited in what characters it would accept and parse as a password.  It's 
abandonware since 2019 - debian recommends to use msmtp:

https://wiki.debian.org/sSMTP

I removed ssmtp and installed msmtp. I think I got the config set up but it is different so I may not have it right. It doesn't work tho. From messages.

Sep 26 10:03:33 Gentoo-1 smartd[27728]: Executing test of <mail> to root ...
Sep 26 10:05:40 Gentoo-1 msmtp[30861]: host=smtp.gmail.com tls=on auth=off from=rdalek1967<at>gmail.com recipients=root errormsg='cannot connect to smtp.gmail.com, port 587: Connection timed out' exitcode=EX_TEMPFAIL
Sep 26 10:05:40 Gentoo-1 smartd[27073]: Test of <mail> to root produced unexpected output (65 bytes) to STDOUT/STDERR:
Sep 26 10:05:40 Gentoo-1 smartd[27073]: mail: cannot send message: Process exited with a non-zero status
Sep 26 10:05:40 Gentoo-1 smartd[27073]: Test of <mail> to root: failed (32-bit/8-bit exit status: 256/1)

Config file:

account default

# The SMTP smarthost
#host mail.oursite.example
host smtp.gmail.com
# Use TLS on port 465. On this port, TLS starts without STARTTLS.
#port 465
port 587
tls on
# tls_starttls off
tls_starttls on
#password sorry
password sorry
# Construct envelope-from addresses of the form "user@oursite.example"
#from %U@oursite.example
from rdalek1967<at>gmail.com
# Do not allow programs to override this envelope-from address via -f
allow_from_override off
# Always set a From header that matches the envelope-from address
set_from_header on

# Syslog logging with facility LOG_MAIL instead of the default LOG_USER
syslog LOG_MAIL

What did I do wrong? ;-)

Dale

:-) :-)