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On cryptographic file storage

In Chapter 3 of Professional Cocoa Application Security, I talk about using CommonCrypto to encrypt files stored on either Mac or iOS file systems. In Chapter 4, I talk about using CommonCrypto to generate Hashed Message Authentication Codes (HMACs) to verify the integrity of messages received by an app. Unfortunately, I didn’t connect the two in the book.

I actually did discuss the reasons for providing an HMAC in a recent talk on cryptographic storage for iOS. But I went to Justin Clark’s talk at Security B-Sides London, where he demonstrated the attacks that are possible against cryptosystems that don’t verify the integrity of their content. This talk was very informative: if the presentation ever makes its way online, I fully recommend that you check it out.

The talk reminded me that there are important attacks I didn’t discuss in the book. So I need to bring these concepts together for the readers of PCAS. The tl;dr version is: if you encrypt content, you must also verify the integrity of the ciphertext. The long version follows.

I recommended in the book using CBC, or Cipher Block Chaining, mode for AES encryption. In this mode, the first block of plaintext is XORed with an Initialization Vector (IV), and this is then encrypted. The resultant ciphertext is then XORed with the second block of plaintext, and this is encrypted. And so on. This offers some protection against certain cryptanalysis attacks that Electronic Code Book (EBC) mode does not: for example, blocks of ciphertext cannot be arbitrarily swapped without the decrypted plaintext becoming nonsensical. A change in the ciphertext not only affects the decryption of the changed block, but also subsequent blocks.

Well, it turns out that this propagating-change property of CBC mode can be used by attackers—if they have information about errors encountered during decryption—to decrypt and encrypt data without needing to discover the key. Ouch. See the B-Sides talk described above (or google for Padding Oracle Attack) for the full details.

Of course, not providing the padding oracle is an important solution to this attack: but refusing to handle content that isn’t verifiably valid avoids any attack involving modified ciphertext: including encrypted content that lies about its length, if that’s an important consideration for your file format. Therefore, if you’re encrypting data in your app, you should be generating an HMAC and verifying that before attempting a decryption operation. Tampered data is not data you want to deal with.