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Seems like this could be avoided by simply approaching the author and offering to pay for a version of the software with the license you want.

That's not an option for Free Software distributions like Debian, so everybody loses except evildoers.

If its not an option for Debian, it is only because of their own peculiarity that it isn't. The type or magnitude of the "payment" is unspecified and open to any negotiation at all. They could even send him an email asking for a GPL license to it in exchange for rewards in the afterlife.

He may not go for it, but they are certainly capable of asking.

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