各ファイルを各自アップロードする必要がある。
Why do we use かく twice in this example? 
How does 自 change the meaning when used?
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From what I understood (I might be wrong though), 各ファイル - Each file. This is following the 各 (prefix) + Noun pattern taught in this lesson.
各自アップロードする - Here, 各自 is an adverbial noun, meaning “individually”, i.e. this part of the sentence means “upload individually”.
Combining the two parts: 各ファイルを各自アップロードする implies “upload each file individually”.
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This makes sense! I agree I think I’ll think about them separately for now
Thanks for your time
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