I run into this surprisingly often and it's become a pet peeve of mine: if you have a URL structure (e.g. for a course website) please make it easy to truncate the URL at every separator in a way that will get me to sibling resources. E.g. I'll often find a link to some lecture notes or a paper for a course website and want to see any other lecture notes for that course.
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The worst and not that rare failure mode is when I end up having to truncate at the professor's home page because that's the longest prefix that can be truncated without a 404 and then you have to do a deep forward search from there to find the siblings.
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