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There are a few pitfalls: File name integrity: signing files one at a time signs the contents of the files. It (typically) does not protect the file names from tampering. This could be disastrous in some situations (e.g. an attacker could change blacklist.txt to whitelist.txt). Set membership integrity: signing individual files does not prevent adding or ...


2

When creating a signed and encrypted PGP message, you only use your own keypair in the signing phase -- it's not used when encrypting the message (that only uses the recipient's public key). The recipient uses their own keypair only to decrypt the message, not to verify the signature. The two keypairs don't interact at all; that's why they don't have to be ...


1

As mentioned this is a very broad question, so please forgive me for not going into any great depth on each point. There are a few ways to beat encryption. One way is to attack the actual math of the cryptography: for PGP that would involve cracking RSA, which would involve finding a way to solve the discrete log problem. This is the hardest method, but ...


1

Signing files individually will create independent signatures for the contents (not filename) of each file. A potential downfall here is that the items could be removed or renamed without detection. Let's say, for example, the files to be signed are alice-invoice, bob-invoice, and chris-invoice. If each file is individually signed, and bob-invoice is ...



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