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My hope is to start with one very conservative, robust, and reasonably harmless test, and have it run by default on as many ooni deb installations as possible. As discussed with Arturo, the http header manipulation test seems like a good candidate.

But once we have that test in mind, how can we get it to run automatically? One idea is for the ooniprobe deb to install a cron entry. To not surprise users too much, should we have the ooniprobe deb install ask the user if they want to set it up to run the conservative tests nightly? (For a noninteractive install, the answer can be an auto no, on the principle of least surprise.)

weasel says

the crontab entry should probably be something like
@daily ooni [ -x /usr/bin/ooni-report ] && /usr/bin/ooni-report

and then he adds

and ooni-report reads /etc/default/ooni to find out what it should
and shouldn't do.
that file probably should be quite simple.  maybe just a shell script
snippet setting REPORT to none|stable|all .
getting the debconf scripting right is a bit of a pain, and complex
formats or data structures increase the pain manyfold.