sendemail TLS Error - New error after of years OK - SMTP of Google

[edudiy]

Hello, thanks for your excellent job.

I'm spanish, from Tenerife ( Canary Island )

I'm trying send a email vía script using your program "sendemail" as always but today show this error:

INFO => Sending: STARTTLS
Mar 17 16:12:19 bttf2 sendemail[9496]: SUCCESS => Received: 220 2.0.0 Ready to start TLS
Mar 17 16:12:19 bttf2 sendemail[9496]: ERROR => TLS setup failed: SSL connect attempt failed error:1416F086:SSL routines:tls_process_server_certificate:certificate verify failed

I had been searching for solution but I don't find it.

My script is the same from 4 years ago and the server hasn't new updates.

sendemail -f "Server <prueba@gmail.com>" -t prueba@gmail.com -s smtp.gmail.com:587 -o message-header=Reintento -u
"Nuevo Intento de Clave fallida" -m "$IP" -v -xu prueba -xp xxxzzzyyy -o tls=yes

I have reviewed the configuration of my account of Google and all OK.

Do you known as solve it ?

All my servers use your program for send emails.

Thanks for all.

[abhi-io]

This worked for me

1. uninstall sendemail
2. apt install apt-transport-https libio-socket-inet6-perl -y
3. curl 'http://ftp.cn.debian.org/debian/pool/main/s/sendemail/sendemail_1.56-5.2~bpo12+1_all.deb' -O
4. dpkg -i sendemail_1.56-5.2~bpo12+1_all.deb

[kyle0r]

@edudiy did you find a solution?

[marioscube]

The solution of @abhi-io worked for me on Debian 12 bookworm.

The new(er) version of sendemail did the trick.

However it did NOT work work with Raspberry PI (RaspiOS based on Debian 12 bookworm):

DEBUG => SMTP-AUTH: LOGIN authenticaion failed.
(authenticaion = no typo, copied from output

On Raspberry pi I did not see the line INFO => Sending: STARTTLS
I saw the line INFO => Sending: AUTH LOGIN
That is different.

This worked with Debian 12 bookworm. (Same login etc)

EDIT:
Missing dependencies on Raspberry Pi
apt install libio-socket-ssl-perl
apt install libnet-ssleay-perl

Then it works!!