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It appears that NSURL’s algorithm for “delete last path component” is to first append ‘../’ and then “normalize” the result, but the latter step can fail for some file URLs, for example with “file://localhost/path/to/https://macromates.com/” it will be stuck at the two slashes (continuing to append ‘../’). Such malformed (file) URL can be created by running ‘mate https://macromates.com/’.