@ekwisner ...
Full disclosure, I have never used Jones and Bartlett, so I really don't know what that interface looks like other than the above screenshot from 2020. And, that interface could have change a bit since then. Also, Stefanie has retired, so you won't be hearing from her any more here in the Canvas Community.
I'm not sure if I am understanding your question correctly, but have you instead tried uploading the *.zip file instead of extracting the files? If you haven't tried uploading the *.zip file, I would try that. When you are on the Import screen within your course "Settings", what option are you using? Have you tried using "QTI .zip file"? It almost sounds like you are using the option "Unzip .zip file into folder". I *think* you might have better luck with "QTI .zip file" instead.
Give that a try and let Community members know if this helps at all. Good luck!
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