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For CBC mode, the IV must be Never used twice with the same key Unpredictable So, in your example (filename$\oplus$key), if you ever encrypt two files that have the same filename with the same key, you will violate #1. Now, you may be tempted to say "but I always generate a new key for every file that I encrypt, so that example doesn't apply". Fine, ...


3

I am using chunks of 1MB and give them a GUID as filename That is fine although unnecessary, the entire input file can be encrypted. These chunks are then first compresses using DEFLATE to minimize attacks based on known Content VERY BAD idea, since you are breaking the input file into pieces, you are now exposing the entropy of specific file ...



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