Hi, I was planning to encrypt my files with GPG for safety before uploading them to the cloud. However, from what I understand GPG doesn’t pad files/do much to prevent file fingerprinting. I was looking around for a way to reliably pad files and encrypt metadata for them but couldn’t find anything. Haven’t found any recommendations on the privacyguides website either. Any help would be appreciated!

Thanks

Any encryption worth being called that randomises itself such that the same file, encrypted twice with the same key, produces completely different ecrypted versions.

To put it another way, if similarities in files could be detected despite their encryption, then the encryption would be worthless.

https://en.m.wikipedia.org/wiki/Ciphertext_indistinguishability

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