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I followed this tutorial to enable email notifications with the unattended upgrades package, however I'm not receiving emails when unattended upgrades runs automatically but when but If I run this command unattended-upgrade -v -d I receive an email notification to my gmail address, In my configuration "mail on error" is disabled.

It's definitely updating packages but doesn't seem to be attempting to send email notifications according to the log, for example this from the other day.

2017-10-27 06:49:45,396 INFO Initial blacklisted packages:
2017-10-27 06:49:45,397 INFO Initial whitelisted packages:
2017-10-27 06:49:45,398 INFO Starting unattended upgrades script
2017-10-27 06:49:45,398 INFO Allowed origins are: ['o=Ubuntu,a=xenial', 'o=Ubuntu,a=xenial-security', 'o=UbuntuESM,a=xenial', 'o=Ubuntu,a=xenial-updates']
2017-10-27 06:49:53,276 INFO Packages that will be upgraded: grub-common grub-efi-amd64 grub-efi-amd64-bin grub-efi-amd64-signed grub2-common libgnutls-openssl27 libgnutls30 wget
2017-10-27 06:49:53,277 INFO Writing dpkg log to '/var/log/unattended-upgrades/unattended-upgrades-dpkg.log'
2017-10-27 06:49:59,266 INFO All upgrades installed

Here's my config for unattended upgrades.

// Automatically upgrade packages from these (origin:archive) pairs
Unattended-Upgrade::Allowed-Origins {
        "${distro_id}:${distro_codename}";
        "${distro_id}:${distro_codename}-security";
        // Extended Security Maintenance; doesn't necessarily exist for
        // every release and this system may not have it installed, but if
        // available, the policy for updates is such that unattended-upgrades
        // should also install from here by default.
        "${distro_id}ESM:${distro_codename}";
        "${distro_id}:${distro_codename}-updates";
//      "${distro_id}:${distro_codename}-proposed";
//      "${distro_id}:${distro_codename}-backports";
};

// List of packages to not update (regexp are supported)
Unattended-Upgrade::Package-Blacklist {
//      "vim";
//      "libc6";
//      "libc6-dev";
//      "libc6-i686";
};

// This option allows you to control if on a unclean dpkg exit
// unattended-upgrades will automatically run
//   dpkg --force-confold --configure -a
// The default is true, to ensure updates keep getting installed
//Unattended-Upgrade::AutoFixInterruptedDpkg "false";

// Split the upgrade into the smallest possible chunks so that
// they can be interrupted with SIGUSR1. This makes the upgrade
// a bit slower but it has the benefit that shutdown while a upgrade
// is running is possible (with a small delay)
//Unattended-Upgrade::MinimalSteps "true";

// Install all unattended-upgrades when the machine is shuting down
// instead of doing it in the background while the machine is running
// This will (obviously) make shutdown slower
//Unattended-Upgrade::InstallOnShutdown "true";

// Send email to this address for problems or packages upgrades
// If empty or unset then no email is sent, make sure that you
// have a working mail setup on your system. A package that provides
// 'mailx' must be installed. E.g. "user@example.com"
Unattended-Upgrade::Mail “myemailaddress@gmail.com";

// Set this value to "true" to get emails only on errors. Default
// is to always send a mail if Unattended-Upgrade::Mail is set
//Unattended-Upgrade::MailOnlyOnError "true";

// Do automatic removal of new unused dependencies after the upgrade
// (equivalent to apt-get autoremove)
//Unattended-Upgrade::Remove-Unused-Dependencies "false";

// Automatically reboot *WITHOUT CONFIRMATION*
//  if the file /var/run/reboot-required is found after the upgrade
//Unattended-Upgrade::Automatic-Reboot "false";
// If automatic reboot is enabled and needed, reboot at the specific
// time instead of immediately
//  Default: "now"
//Unattended-Upgrade::Automatic-Reboot-Time "02:00";

// Use apt bandwidth limit feature, this example limits the download
// speed to 70kb/sec
Acquire::http::Dl-Limit "1000";

Any help with this would be very much appreciated, I've Googled a lot and cannot seem to find an answer to why this isn't working. I do also have heirloom-mailx installed and a working .mailrc.

Thank you!

1

Check /var/log/mail.log to see what's going wrong, it's usually the "from:" field that's borked and gets blocked by the upstream SMTP server.

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