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I have a simple script at /etc/network/if-up.d/test containing the following line

date >> /var/log/testing.log

Running that script manually works fine. However, rebooting the system runs it twice. And disconnecting/reconnecting the ethernet cable does not run it at all. How can I make it work in all 3 scenarios?

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It is being run twice at startup because it is running for both the loopback (lo) and ethernet interface(eth0).

Try this in your script. It should show the interface name.

echo $IFACE  >> /var/log/testing.log

The man page for ifup has this note:

Note that the program does not run automatically: ifup alone does not bring up interfaces that appear as a result of hardware being installed ...

According to the same man page ifplugd may be an option.

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