I'm facing exactly this issue. Have you found a work-around for it?

Actually, the hack described in this changelist is working for me: https://github.com/Homebrew/brew/pull/9102/files/4665bb8e663c6d0ef452f4c124742732c96f8fd6#diff-f7b3993a53e62a7bdff250c5b7b176cc03232622c2a3c9912a496a3f82211884 Specifically this: If the codesigning fails, it may be a bug in Apple's codesign utility A known workaround is to copy the file to another inode, then move it back erasing the previous file. Then sign again. # TODO: remove this once the bug in Apple's codesign utility is fixed Dir::Tmpname.create("workaround") do |tmppath| FileUtils.cp file, tmppath FileUtils.mv tmppath, file, force: true end