12

I updated sSMTP to version 2.61 and now when I try to us it I receive the following error:

ssmtp: Cannot open smtp.gmail.com:587

I can connect via telnet to their address, but sSMTP seems to get tripped up and Im not sure what changed after the update.

Here is the ssmtp.conf

root=XXXXX@gmail.com
mailhub=smtp.gmail.com:587
RewriteDomain=gmail.com
Hostname=localhost
UseTLS=YES
UseSTARTTLS=Yes
AuthUser=XXXXX
AuthPass=XXXXX
FromLineOverride=yes

Output when connecting via telnet:

[root@soupcan sbin]# telnet smtp.gmail.com 587
Trying 74.125.142.108...
Connected to smtp.gmail.com.
Escape character is '^]'.
220 mx.google.com ESMTP l7sm7330049igx.2 - gsmtp
quit
221 2.0.0 closing connection l7sm7330049igx.2 - gsmtp
Connection closed by foreign host.

And the output when I try to use sSMTP

[root@soupcan sbin]# /usr/sbin/ssmtp -v XXXXX@gmail.com < /home/user/Documents/Scripts/msg.txt
[<-] 220 mx.google.com ESMTP f5sm7367852igc.4 - gsmtp
[->] EHLO localhost
[<-] 250 CHUNKING
[->] STARTTLS
[<-] 220 2.0.0 Ready to start TLS
ssmtp: Cannot open smtp.gmail.com:587

EDIT Turning on debug logging I now see this, Im still digging:

SSL not working: certificate verify failed (20)

EDIT 2 This has been resolved by adding the following to my ssmtp.conf file

TLS_CA_File=/etc/pki/tls/certs/ca-bundle.crt

Found information from HERE and HERE

ProfessionalAmateur
  • 3,185
  • This is what works for me, on Ubuntu 16.04 and on Raspbian. https://unix.stackexchange.com/questions/363814/simplest-way-to-send-one-line-mail-out-via-command-line-using-gmail/363815#363815 – SDsolar Jul 22 '17 at 07:29
  • You need to be using this: mailhub=smtp.gmail.com:465 – SDsolar Sep 10 '17 at 06:28

3 Answers3

14

This has been resolved by adding the following to my ssmtp.conf file

TLS_CA_File=/etc/pki/tls/certs/ca-bundle.crt

Found information from HERE and HERE

ProfessionalAmateur
  • 3,185
  • It was failing for me until commented out #UseTLSCert=YES, TLS_CA_File=/etc/pki/tls/certs/ca-bundle.crt, UseTLS=YES, UseSTARTTLS=YES, FromLineOverride=YES, Hostname=/run hostname command to find out/, RewriteDomain=my.domain.ext, mailhub=smtp.office365.com:587 – webcoder.co.uk Dec 21 '22 at 16:36
3

FYI -- For Ubuntu the .crt file is in a different place and should read:

TLS_CA-File=/etc/ssl/certs/ca-certificates.crt

Adding this enabled me to connect to my SMTP server via STARTTLS on port 587 with the settings:

mailhub=smtp.{myserver}.com:587
AuthUser={username}    
AuthPass={password}
UseSTARTTLS=YES 
UseTLS=NO
TLS_CA_File=/etc/ssl/certs/ca-certificates.crt

My mail server is configured to use STARTTLS and not SSL or TLS.

If I set UseTLS=YES, it fails. It has to be exclusively UseSTARTTLS=YES, not both. I don't know if other mail servers can do both at the same time, but mine does not.

slm
  • 369,824
hoekma
  • 139
1

Use the setup found here:

Simplest way to send one-line mail out via command line using gmail?

Excerpt:

root=rpi3abc@gmail
mailhub=smtp.gmail.com:465
FromLineOverride=YES
AuthUser=rpi3abc@gmail.com
AuthPass=testing123
UseTLS=YES

It is as simple as that.

SDsolar
  • 1,849