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I have the GSmartControl GUI utility installed and would like to create a routine schedule for running short and extended tests in the background, and be notified of any failures (or increase in any of the metrics which indicate problems) via a popup or something similar.

I've done manual tests using the smartctl tool using the command line, and even hooked up some combination of manual cron schedules and notification rules in the past, but I am looking for a 100% (or as close to 100% as possible) GUI solution at the moment. Is there a way to accomplish this?

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This answer is about notification.
As far I know the modern Ubuntu includes smartd.service (from smartmontools):

$ systemctl status smartd.service
* smartd.service - Self Monitoring and Reporting Technology (SMART) Daemon
   Loaded: loaded (/lib/systemd/system/smartd.service; enabled; vendor preset: enabled)
   Active: active (running) since Tue 2018-07-31 17:27:05 MSK; 2 days ago
     Docs: man:smartd(8)
           man:smartd.conf(5)
 Main PID: 1044 (smartd)
   CGroup: /system.slice/smartd.service
           `-1044 /usr/sbin/smartd -n

Aug 02 17:57:05 user-pc smartd[1044]: Device: /dev/sda [SAT], SMART Usage Attribute: 190 Airflow_Temperature_Cel changed from 60 to 58

There is a GUI notifier dependent on smartmontools. It is named smart-notifier. Below is its description:

Description-en: graphical hard disk health status notifier
A graphical notifier for smartmontools which attempts to show messages from the smartd disk monitoring daemon to the user. Currently only for gtk.

From its man smart-notifier :

DESCRIPTION
This manual page documents briefly the smart-notifier.

smart-notifier is a dbus service/client pair. If run without options, it starts a dbus service and listens formessages send by the client (normally started from a script in /etc/smartd/run.d). This messages are then displayed on the screen of the user running the service. This program is designed to be added to the session of the user.

It should inform you about attribute changes. But some scripting may be needed.

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