Loading static files from a dev environment

I'm having an odd problem with my test Django environment.

It seems that static filles I've collected from different apps using
the collectstatic command works fine, while other static files I
placed in myself result in 404 error. This can happen from the same
directory (where a png that was collected will load, but a png i just
drop in will fail).

all files have the same permissions, and I can't figure out why this
would happen. I'm currently able to solve this by serving the files
through ngnix - but I really shouldn't need to do that.

Any ideas why this might be happening ?

Thanks

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