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I first generate a keyfile with openssl rand -hex 64 -out keyfile.

I then encrypt the file with openssl enc -aes-256-cbc -salt -in large_file.zip -out large_encrypted.bin -pass file:./keyfile.

I am encrypting files sized anywhere from a few bytes to 1TB. I will be using this in a simple bash script.

  1. Is this secure in 2021? Should I use a different cipher?
  2. Can any metadata leak from the encrypted file?
  3. Should/can the keyfile be larger than 64 bytes?
  4. Should I create new keyfiles for each file I encrypt?
  5. Is there a minimum/maximum file size this can encrypt? Do different file sizes affect security?
  6. Is this considered "rolling my own crypto" (which I know is widely discouraged)?
henderson
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