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The post_checkout hook is executed after making change to an existing plugin, i.e. after downloading update or switching to different commit/branch/tag locally.

What you probably experience is that it doesn't trigger on the initial install. There is post_install hook for that. Try adding the same function in the post_install hook. If the hook itself executes but throws an error (although I don't think it should in this particular case), try executing the same function inside later().

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Answer selected by echasnovski
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