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 [email protected] 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 [email protected] >/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 = [email protected]
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)
Build msmtp using --with-tls=openssl to solve the problem.
As regards as the EHLO command sent twice the RFC3207 states:
The server MUST discard any knowledge obtained from the client, such as the argument to the EHLO command, which was not obtained from the TLS negotiation itself. The client MUST discard any knowledge obtained from the server, such as the list of SMTP service extensions, which was not obtained from the TLS negotiation itself. The client SHOULD send an EHLO command as the first command after a successful TLS negotiation.
So that is the normal behaviour.