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I use SSMTP on many of our servers. As of June 6th 2019 I can no longer get SSMTP on any of my ubuntu servers to send email. I have some raspberry pies using the same scripts and they send just fine. On site and offsite using different Google domain names stopped sending, so its not tied to one specific Google apps domain. Nor is it tied to a specific network. All systems are running 18.10. Other things using this same account, send fine, through Ubuntu. PHP mailings for example.

It also does not matter what user I try to use within each Google domain. I can use SSMTP with a yahoo user and that sends from Ubuntu.

When I do ssmtp with -v on a linux box I see: 

[<-] 220 smtp.gmail.com ESMTP b6sm3003334iok.71 - gsmtp
[->] EHLO munki.xxxxx.com
[<-] 250 SMTPUTF8
[->] STARTTLS
[<-] 220 2.0.0 Ready to start TLS
[->] EHLO munki.xxxxx.com
[<-] 
ssmtp:  (munki.xxxxx.com)

When I do the same on a pi I see:

[<-] 220 smtp.gmail.com ESMTP w23sm3846674iod.12 - gsmtp
[->] EHLO upsd-c03.xxxxx.com
[<-] 250 SMTPUTF8
[->] STARTTLS
[<-] 220 2.0.0 Ready to start TLS
[->] EHLO upsd-c03.xxxxx.com
[<-] 250 SMTPUTF8
[->] AUTH LOGIN
[<-] 334 Vjjl;hbWU6
[->] bmFnaW9zQG5XJzLm9yZw==
[<-] 334 UGFzc3dvcmQ6
[<-] 235 2.7.0 Accepted
[->] MAIL FROM:<root@upsd-c03.xxxxx.com>
[<-] 250 2.1.0 OK w23sm38674iod.12 - gsmtp
[->] RCPT TO:<jcody@jwsadda.net>
[<-] 250 2.1.5 OK w23sm38674iod.12 - gsmtp
[->] DATA
[<-] 354  Go ahead w23sm3874iod.12 - gsmtp
[->] Received: by upsd-c03.xxxxx.com (sSMTP sendmail emulation); Fri, 14 Jun 2019 16:59:33 -0500
[->] From: "root" <root@upsd-c03.xxxxx.com>
[->] Date: Fri, 14 Jun 2019 16:59:33 -0500
[->] test
[->] 
[->] .
[<-] 250 2.0.0 OK  1560549575 w23sm3846iod.12 - gsmtp
[->] QUIT
[<-] 221 2.0.0 closing connection w23sm3846iod.12 - gsmtp

Just wondering if anyone else using Google to send email with SSMTP has seen the same behavior? I haven't tested an 18.04 or 19.04.

Thank you!!

Jim

Jim Cody
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  • Any chance that the problem actually started on 6/2/2019? Are all of the Ubuntu servers that don't work in the same domain as munki.xxxxx.com? – heynnema Jun 14 '19 at 22:46
  • See https://glockapps.com/blog/remove-ip-address-gmail-blacklist/ – heynnema Jun 14 '19 at 22:51
  • See https://glockapps.com/ – heynnema Jun 14 '19 at 22:52
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    It is a little sideways of your issue but I changed from sSMTP to msmtp quite some time ago and have never regretted it. Perhaps this change might sidestep whatever issue you are having? msmtp is constantly developed while sSMTP is undeveloped for many years now... – andrew.46 Jun 15 '19 at 11:16
  • I have tried 3 different domains all within google apps, and all 3 work on the raspberry pi's but do not work on Ubuntu using ssmtp. Other programs can send using the credentials so I know we are not blocked by any blacklist. – Jim Cody Jun 15 '19 at 18:00
  • There is a chance it could have been 6/2/19 as I only noticed it on June 6th. Did anything happen that day that you know of??? – Jim Cody Jun 15 '19 at 18:01
  • I ready about moving to msmtp but didn't want to do that if I fix this as I have so much setup to use SSMTP. That will probably be what I end up doing. :) – Jim Cody Jun 15 '19 at 18:01
  • Just in case I forget to later, THANK YOU for the ideas. I really have been scratching my head on this. :) – Jim Cody Jun 15 '19 at 18:03
  • I have the same issue in reverse - I replaced a RaPi3 with a RaPi4 (and fresh Rasperian) and ssmtp no longer works on the new RaPi - still works on my older Linux Mint distro just fine - using the exact same config and same network – Mtl Dev Nov 05 '19 at 20:34

0 Answers0