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I want to automatically update a Debian system (actually Debian Wheezy on Raspberry Pi, though that shouldn't make much a difference). I've already seen that there is cron-apt, probably a good choice, as it also includes mail notifications on errors.

I am however not sure about updates involving reboots like e.g. new kernel updates? Does cron-apt automatically reboot a system after a new kernel image was installed? Or can it at least notify me on update of specific packages?

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No decent default configuration will automatically reboot, this could be extremely aggravating. –  Gilles Jun 23 '12 at 23:35

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Have a look at unattended-upgrades. As this is run via cron you'll get emails after packages are updated. unattended-upgrades won't restart your system.

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Thanks, I only want mails on errors and kernel updates, is that possible? –  stefan.at.wpf Jun 24 '12 at 8:09
    
@stefan.at.wpf without any configuration, no. But look into apt-dater. You can also try to determine if the current running kernel is the latest one e.g . do the notification not via the upgrade mechanism but something else. –  Ulrich Dangel Jun 24 '12 at 9:36

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