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If I install Tiger, will it overwrite the contents within /etc and /usr? I have some CLI programs saved in those two folders (not put by me; but by installation packages).
If it has a different version of a file that already exists, it is likely to overwrite that file. However, if you have a file that Tiger doesn't install any version of, then it should leave those files alone.
You are in Soviet Russia. It is dark. Grue is likely to be eaten by YOU!
The installer might overwrite the folder, it might overwrite the files IN the folder. Worst case - reinstall the app that put them there. Back the folders up if you're not sure.
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