It may depend on what kind of file format you have for the file.
If you have a 25 second .wav file, it will take longer to upload than it will for a 25 second .mp3 file.
It may be your internet fluctuating on its strength sometimes. Make sure that when you upload something, be wary of other users connected to your network using bandwith, so you won't get as much as you would with full internet-bandwith to yourself.
It may also just be if you put the specific file you want to upload in a long directory path, which is hardly a problem, just a possibility.
If you have any other re-occurring problems with Roblox, contact the administrators through an email.
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