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Then we hit the problem that if we don't push that request at users, probably a tiny fraction will turn it on.

Worse, that fraction will be the statistically unusual people who bother reading and finding such options, meaning we can't derive any statistically useful results about the user base from them!

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Frankly, that's your problem. I don't see even a true desire to make the software better as a legitimate reason to exfiltrate data from people without asking.

Maybe you should ask them better. For example you could ask for help on the home page of your project or in the beginning of a tutorial. Or maybe they do not want to paticipate. Is it right to ignore this and turn analytics on by default?

The Debian installer gets this right: it prompts you during the install whether it can collect information about installed packages for popcon[1]

[1] http://popcon.debian.org/

I never understood why popcon is necessary. Couldn't you achieve about the same result by just counting downloads on the package mirrors?

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