I've looked through the list of possible solutions, but I don't see this problem, here it is.
I had been using smtp for years for my crontab entry to provide status updates via email. Then it quit this week, and I was unable to fix it. Then I saw that it had become orphaned, and the suggestion was to move to msmtp. So I downloaded and installed it on my Ubuntu 18.10 system.
I'm trying to send email to my myaccount@gmail.com account. It appears that I'm communicating properly with the gmail smtp server, as the debug below show. But it always gets a TLS Timeout.
I also don't understand why I have multiple EHLO entries. My system does not have a DNS domain name, so that I'm not sure what to put here; localhost seems to be working OK. Also, my Thunderbird emailer is working correctly with gmail.
Here's the debug output:
echo "Hello there" | msmtp --debug myaccount@gmail.com >/tmp/msmtpOut.txt
ignoring system configuration file /etc/msmtprc: No such file or directory
loaded user configuration file /home/myhome/.msmtprc
falling back to default account
using account default from /home/myhome/.msmtprc
host = smtp.gmail.com
port = 587
proxy host = (not set)
proxy port = 0
timeout = off
protocol = smtp
domain = localhost
auth = choose
user = myaccount
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 = myaccount@gmail.com
add_missing_from_header = on
dsn_notify = (not set)
dsn_return = (not set)
logfile = (not set)
syslog = (not set)
aliases = (not set)
reading recipients from the command line
<-- 220 smtp.gmail.com ESMTP 4sm116524ywc.22 - gsmtp
--> EHLO localhost
<-- 250-smtp.gmail.com at your service, [71.56.87.81]
<-- 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 certificate information:
Owner:
Common Name: smtp.gmail.com
Organization: Google LLC
Locality: Mountain View
State or Province: California
Country: US
Issuer:
Common Name: Google Internet Authority G3
Organization: Google Trust Services
Country: US
Validity:
Activation time: Tue 21 May 2019 04:48:45 PM EDT
Expiration time: Tue 13 Aug 2019 04:32:00 PM EDT
Fingerprints:
SHA256: C7:78:B6:D6:4E:3E:2B:2F:08:6D:A4:84:E6:1D:87:8E:A1:DF:54:D2:AB:79:AC:A6:BB:50:E5:5D:EC:B4:20:4C
SHA1 (deprecated): 39:C5:E5:40:64:37:17:25:17:7F:E8:BA:20:F4:70:F4:FE:22:70:22
--> EHLO localhost
msmtp: cannot read from TLS connection: the operation timed out
msmtp: could not send mail (account default from /home/myhome/.msmtprc)