Click unfortunately doesn't pass the smell test of a non-awkward implementation of 'sudo'. It gets some partial credit because an implementation is possible but only because you can subclass the click.Command object and change the parsing behavior arbitrarily.

So many of these parsing libraries seem to forget that any positional parameter can stop options parsing not just '--' and that that parameter might appear arbitrarily deep in subcommands.

This is not only needed for commands like sudo and ssh but BSD style CLIs as well which all OSX users are probably intimately familiar and annoyed with.