Configuring ssmtp

I'm sure someone here has configured ssmtp to send mail to their gmail/google account. While I think I've done everything correctly, a second set of eyes always seems to help. I've installed mailutils and ssmtp and edit the ssmtp.conf file in /etc/ssmtp. Here it is, with the secure info redacted by ****:

#
# Config file for sSMTP sendmail
#
# The person who gets all mail for userids < 1000
# Make this empty to disable rewriting.
# root=postmaster

I tried the above both commented and uncommented. No change.

# The place where the mail goes. The actual machine name is required no 
# MX records are consulted. Commonly mailhosts are named mail.domain.com
# mailhub=mail
root=****@gmail.com
mailhub=smtp.gmail.com:587
AuthUser=****@gmail.com
AuthPass=**** **** **** **** 
UseTLS=YES
UseSTARTTLS=YES

# Where will the mail seem to come from?
#rewriteDomain=

# The full hostname
hostname=r710 # The hostname of my Dell r710 server

# Are users allowed to set their own From: address?
# YES - Allow the user to specify their own From: address
# NO - Use the system generated From: address
#FromLineOverride=YES
FromLineOverride=YES

The AuthPass given above is a 16-character application password created under my Google account. I've tried using both the hostname and "ssmtp" as the app name. But Google rejects a test message:
echo "This is a test message" | ssmtp -v ****@gmail.com
with

[<-] 220 smtp.gmail.com ESMTP af79cd13be357-7c958ea4893sm485002585a.112 - gsmtp
[->] EHLO r710
[<-] 250 SMTPUTF8
[->] AUTH LOGIN
[<-] 334 VXNlcm5hbWU6
[->] ZnJlZC5wdWhhbkBnbWFpbC5jb20=
[<-] 334 UGFzc3dvcmQ6
[<-] 535 5.7.8  https://support.google.com/mail/?p=BadCredentials af79cd13be357-7c958ea4893sm485002585a.112 - gsmtp
ssmtp: Authorization failed (535 5.7.8  https://support.google.com/mail/?p=BadCredentials af79cd13be357-7c958ea4893sm485002585a.112 - gsmtp)

I can see the "hello" (EHLO) acknowledges my hostname (r710) but then throws a 535 5.7.8 error. Google's error codes indicate
Application-specific password required. For more information, go to Sign in with app passwords.
I'm guessing I haven't properly set the app name in my Google settings, or there's a config setting I've overlooked or entered incorrectly.

See anything?

Hopefully, this can help.

1 Like

Thank you for the links. Unfortunately, I didn't learn anything new or helpful from them that I haven't already tried.

But...

Google isn't the only email provider. Before Google was even a search engine, I have been a customer of an ISP that began life as a BBS. These folks are wonderful, responsive, tech-savvy and very helpful. I figure I've been with them since about 1988. They host my "real" email address (as well as a web site I maintain) that I don't give out to anyone except my family, my bank and those I "need" to maintain contact with.

So, I decided to try them instead of Google. At first, I didn't think they supported SMTP and used only IMAP or POP3. But I was wrong. IMAP is used for receiving mail, but SMTP can be used for sending mail. Sadly, I didn't learn that until I'd spent much of the day watching baseball and mucking around with mutt and Evolution (which is installed on my machine).

On a side note, my login id is NOT the same as my email login, and I could find no way in Evolution to change that. Weird? But? Design choice? Regardless, I won't be using Evolution. Ever.

A bit of minor tweaking of my /etc/ssmtp/ssmtp.conf file to point to my ISP's email account, and off I went. Zounds! Success on the first try! But I check my other account's inbox (to where I'd send my test message) and: Nothing. A couple more tries. Then, all of a sudden I had multiple test messages (NOT dupes) in my inbox! Must have been some latency upline. All that was missing was a Subject: line. I can't find any instructions on how to accomplish this, but that's the least of my problems. Here's a sample test message I sent:

echo "Your IP address has changed to curl ipinfo.io/ip" | ssmtp -v -f [email protected] [email protected] -- the -v is only to show verbosity, and won't be used as I implement this in my automation process.

Just a heads up. A couple of years ago, I ran into some roadblocks with using POP3/IMAP for GMail. I still use regular password login for Yahoo/Rogers.

I was forced to abandon my regular password-driven approach for the Port 995 SSL/TLS connection and implement OAuth2, which is my current method.

I can't remember what Google gave as the reason to force the switchover at the time. Thought I should share that with you.

(P.S. I haven't faced sufficient urgency to learn about SMTP to replace my interraction with my eMail service providers.)