Hi @mb4698 
You do not upload files to "Student View"; but rather, as a test student using student view, you can upload a file anywhere within the Canvas classroom that permits a student upload - assignments, discussion board, specified quiz questions etc.
If you are thinking that when in Student View and acting as the test student, that you should be able to upload to the "Files" section of the test student account, you cannot. Actions as a test student are limited to the course in which you selected Student View.
However, for more extensive testing - such as uploading files, we created "dummy students" in our account. You might want to check with your School's Canvas Admin to see if some are available for you to use since most admins do create them.
Kelley
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