drew@ilium~$ echo "Hello there" | msmtp --debug xxxxxxxxxxxxxxxxxxx@gmail.com
ignoring system configuration file /etc/msmtprc: No such file or directory
loaded user configuration file /home/andrew/.msmtprc
falling back to default account
using account default from /home/andrew/.msmtprc
host = smtp.gmail.com
port = 587
source ip = (not set)
proxy host = (not set)
proxy port = 0
timeout = off
protocol = smtp
domain = localhost
auth = choose
user = xxxxxxxxxxxxxxxxxxx@gmail.com
password = *
passwordeval = (not set)
ntlmdomain = (not set)
tls = on
tls_starttls = on
tls_trust_file = /etc/ssl/certs/ca-certificates.crt
tls_crl_file = (not set)
tls_fingerprint = (not set)
tls_key_file = (not set)
tls_cert_file = (not set)
tls_certcheck = on
tls_min_dh_prime_bits = (not set)
tls_priorities = (not set)
auto_from = off
maildomain = (not set)
from = xxxxxxxxxxxxxxxxxxx@gmail.com
add_missing_from_header = on
add_missing_date_header = on
remove_bcc_headers = on
dsn_notify = (not set)
dsn_return = (not set)
logfile = /home/andrew/.msmtp.log
logfile_time_format = (not set)
syslog = (not set)
aliases = (not set)
reading recipients from the command line
<-- 220 smtp.gmail.com ESMTP z15-20020aa791cf000000b005dd65169623sm4234372pfa.190 - gsmtp
--> EHLO localhost
<-- 250-smtp.gmail.com at your service, [60.242.146.221]
<-- 250-SIZE 35882577
<-- 250-8BITMIME
<-- 250-STARTTLS
<-- 250-ENHANCEDSTATUSCODES
<-- 250-PIPELINING
<-- 250-CHUNKING
<-- 250 SMTPUTF8
--> STARTTLS
<-- 220 2.0.0 Ready to start TLS
TLS session parameters:
    (TLS1.3)-(ECDHE-X25519)-(ECDSA-SECP256R1-SHA256)-(AES-256-GCM)
TLS certificate information:
    Owner:
        Common Name: smtp.gmail.com
    Issuer:
        Common Name: GTS CA 1C3
        Organization: Google Trust Services LLC
        Country: US
    Validity:
        Activation time: Thu 02 Mar 2023 15:22:24
        Expiration time: Thu 25 May 2023 14:22:23
    Fingerprints:
        SHA256: 96:E0:5B:72:0D:E7:5D:B4:50:8D:83:2D:7D:3B:6E:61:D3:BF:6A:09:9C:AA:6A:37:6E:7D:4C:29:5C:CB:E3:77
        SHA1 (deprecated): B3:FB:FA:39:09:17:68:51:2B:C4:2B:9C:0C:71:80:9E:33:09:55:3B
--> EHLO localhost
<-- 250-smtp.gmail.com at your service, [60.242.146.221]
<-- 250-SIZE 35882577
<-- 250-8BITMIME
<-- 250-AUTH LOGIN PLAIN XOAUTH2 PLAIN-CLIENTTOKEN OAUTHBEARER XOAUTH
<-- 250-ENHANCEDSTATUSCODES
<-- 250-PIPELINING
<-- 250-CHUNKING
<-- 250 SMTPUTF8
--> AUTH PLAIN AGFuZHJldy5kYXZpZC5zdHJvbmdAZ21haWwuY29tAHFybnR1amlkdWVjZmV6anc=
<-- 235 2.7.0 Accepted
--> MAIL FROM:<xxxxxxxxxxxxxxxxxxx@gmail.com>
--> RCPT TO:<xxxxxxxxxxxxxxxxxxx@gmail.com>
--> DATA
<-- 250 2.1.0 OK z15-20020aa791cf000000b005dd65169623sm4234372pfa.190 - gsmtp
<-- 250 2.1.5 OK z15-20020aa791cf000000b005dd65169623sm4234372pfa.190 - gsmtp
<-- 354  Go ahead z15-20020aa791cf000000b005dd65169623sm4234372pfa.190 - gsmtp
--> From: xxxxxxxxxxxxxxxxxxx@gmail.com
--> Date: Sun, 19 Mar 2023 19:32:22 +1100
--> Hello there
--> .
<-- 250 2.0.0 OK  1679214769 z15-20020aa791cf000000b005dd65169623sm4234372pfa.190 - gsmtp
--> QUIT
<-- 221 2.0.0 closing connection z15-20020aa791cf000000b005dd65169623sm4234372pfa.190 - gsmtp
andrew@ilium~$