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URLs with two consecutive slashes in the path are usually garbage/broken. But I remember some issue with the dev server related to double slashes (pallets/werkzeug#822). Can you try if it also breaks when using a real WSGI container instead? gunicorn is probably the quickest way to test this.
The regex for PathConverter matches anything that doesn't start with a /, as absolute paths are typically a bad idea to let users enter. If you need your own converter that does something different, you can write and register one the same way the others are.
All the 404 stuff should be intercepted but aren't.
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