Setup unattended upgrades on Ubuntu with Gmail

ubuntu_unattended_upgrades_gmail.markdown

Install the unattended-upgrades package

$ sudo apt-get install unattended-upgrades 

Edit the periodic configuration

$ sudo nano /etc/apt/apt.conf.d/10periodic

Set the following:

APT::Periodic::Update-Package-Lists "1";
APT::Periodic::Download-Upgradeable-Packages "1";
APT::Periodic::AutocleanInterval "7";

Where the number is the frequency (in days)

Edit the unattended upgrades configuration

$ sudo nano /etc/apt/apt.conf.d/50unattended-upgrades

Configure the default packages you want to automatically upgrade:

Unattended-Upgrade::Allowed-Origins {
        "${distro_id}:${distro_codename}-security";
        "${distro_id}:${distro_codename}-updates";
//      "${distro_id}:${distro_codename}-proposed";
//      "${distro_id}:${distro_codename}-backports";
};

Optionally configure additional packages you want to upgrade

In order to automatically upgrade custom packages do the following:

1. Look in /var/lib/apt/lists/ to find the custom package that you want to update. It should end with Release e.g. /var/lib/apt/lists/files.freeswitch.org_repo_deb_debian_dists_wheezy_InRelease
2. Open up the file $ nano /var/lib/apt/lists/files.freeswitch.org_repo_deb_debian_dists_wheezy_InRelease
3. Look for the Origin and Suite entries. e.g. Origin: freeswitch Suite: stable and note these values.
4. Edit the unattended upgrades configuration again. $ sudo nano /etc/apt/apt.conf.d/50unattended-upgrades
5. Add an entry for the origin and suite in the configuration

E.g.

Unattended-Upgrade::Allowed-Origins {
        "${distro_id}:${distro_codename}-security";
        "${distro_id}:${distro_codename}-updates";
        "freeswitch:stable";
//      "${distro_id}:${distro_codename}-proposed";
//      "${distro_id}:${distro_codename}-backports";
};

Setup automatic reboot (optional)

This will reboot the server if required automatically.

Unattended-Upgrade::Automatic-Reboot "true";
Unattended-Upgrade::Automatic-Reboot-Time "19:00"; // Optional

Setup Mail

Unattended-Upgrade::Mail "someone@gmail.com";

Send notifications via Gmail

Install mailx

$ heirloom-mailx

Set mail defaults

$ sudo su
$ cd ~
$ nano .mailrc

Add the following to .mailrc in root's home directory.

set smtp-use-starttls
set ssl-verify=ignore
set smtp=smtp://smtp.gmail.com:587
set smtp-auth=login
set smtp-auth-user=someone@gmail.com
set smtp-auth-password=secret
set from="someone@gmail.com

Change the permissions of .mailrc

chmod 400 .mailrc

Test it out

$ sudo unattended-upgrade -v -d --dry-run

Trigger it now

$ sudo unattended-upgrade -v -d

I managed to set up the upgrades, but it still won't send email even though I've configured it the same way.
I can email via the terminal using mailx -v -s "subject" some@mail.com, but unattended-upgrades keeps failing to email me.

/etc/apt/apt.conf.d/50unattended-upgrades has the Unattended-Upgrade::Mail uncommented and set to my email. However, in /var/spool/mail it says this (The CENSORED is a placeholder for my email and server name etc.):

----- Transcript of session follows -----
... while talking to aspmx.l.google.com.:
>>> DATA
<<< 550-5.7.1 [<CENSORED>] Our system has detected that this message does
<<< 550-5.7.1 not meet IPv6 sending guidelines regarding PTR records and
<<< 550-5.7.1 authentication. Please review
<<< 550-5.7.1  https://support.google.com/mail/?p=ipv6_authentication_error for more
<<< 550 5.7.1 information. c125si9979221wmd.11 - gsmtp
554 5.0.0 Service unavailable

--tB969CY2007824.1449641352/pla39
Content-Type: message/delivery-status

Reporting-MTA: dns; <CENSORED>
Received-From-MTA: DNS; localhost.localdomain
Arrival-Date: Wed, 9 Dec 2015 07:09:11 +0100

Final-Recipient: RFC822; <CENSORED>@gmail.com
Action: failed
Status: 5.7.1
Remote-MTA: DNS; aspmx.l.google.com
Diagnostic-Code: SMTP; 550-5.7.1 [<CENSORED>] Our system has detected that this message does
Last-Attempt-Date: Wed, 9 Dec 2015 07:09:12 +0100

--tB969CY2007824.1449641352/pla39
Content-Type: text/rfc822-headers

Return-Path: <root@<CENSORED>>
Received: from <CENSORED> (localhost.localdomain [127.0.0.1])
        by <CENSORED> (8.14.4/8.14.4/Debian-8) with ESMTP id tB969BY2007822
        for <<CENSORED>@gmail.com>; Wed, 9 Dec 2015 07:09:11 +0100
Received: (from root@localhost)
        by <CENSORED> (8.14.4/8.14.4/Submit) id tB969AGA007820;
        Wed, 9 Dec 2015 07:09:10 +0100
Date: Wed, 9 Dec 2015 07:09:10 +0100
From: root <root@<CENSORED>>
Message-Id: <201512090609.tB969AGA007820@<CENSORED>>
Subject: [reboot required] unattended-upgrades result for '<CENSORED>': True
To: <CENSORED>@gmail.com
MIME-Version: 1.0
Content-Type: text/plain; charset="utf-8"
Content-Transfer-Encoding: quoted-printable

--tB969CY2007824.1449641352/pla39--

This doesn't make sense, since
mailx -v -s "subject" some@gmail.com works fine
The .mailrc is in the root's home folder, owner by root and with the correct permissions (400)

Any clue why it won't work?

It sounds like your server is connecting to gmail's SMTP server via IPv6, but it is a missing a reverse DNS entry for that IP. You'll need to get a reverse DNS record created by your host. Found here: http://serverfault.com/questions/538050/gmail-does-not-accept-mail-from-a-new-server

how do u install mailx?

root@thaiprochat:~# apt install mailx
Reading package lists... Done
Building dependency tree
Reading state information... Done
Package mailx is a virtual package provided by:
s-nail 14.8.6-1
mailutils 1:2.99.99-1ubuntu2
bsd-mailx 8.1.2-0.20160123cvs-2
You should explicitly select one to install.

E: Package 'mailx' has no installation candidate

You do not need to install mailx to be able to send notifications via Gmail. See here.

It works perfect in Ubuntu 14.04 but it doesn't work in Ubuntu 16.04 or 18.04... I think it is something relative to systemd + environments.
The final solution that works for me was install sendmail.