SoK: Why Johnny Can't Fix PGP Standardization

Pretty Good Privacy (PGP) has long been the primary IETF standard for encrypting email, but suffers from widespread usability and security problems that have limited its adoption. As time has marched on, the underlying cryptographic protocol has fallen out of date insofar as PGP is unauthenticated on a per message basis and compresses before encryption. There have been an increasing number of attacks on the increasingly outdated primitives and complex clients used by the PGP eco-system. However, attempts to update the OpenPGP standard have failed at the IETF except for adding modern cryptographic primitives. Outside of official standardization, Autocrypt is a "bottom-up" community attempt to fix PGP, but still falls victim to attacks on PGP involving authentication. The core reason for the inability to "fix" PGP is the lack of a simple AEAD interface which in turn requires a decentralized public key infrastructure to work with email. Yet even if standards like MLS replace PGP, the deployment of a decentralized PKI remains an open issue

An Attack on CFB Mode Encryption as Used by OpenPGP

This paper describes an adaptive-chosen-ciphertext attack on the Cipher Feedback (CFB) mode of encryption as used in OpenPGP. In most circumstances it will allow an attacker to determine 16 bits of any block of plaintext with about 2 oracle queries for the initial setup work and 2 oracle queries for each block. Standard CFB mode encryption does not appear to be a#ected by this attack. It applies to a particular variation of CFB used by OpenPGP. In particular it exploits an ad-hoc integrity check feature in OpenPGP which was meant as a "quick check" to determine the correctness of the decrypting symmetric key

Automated Analysis of Protocols that use Authenticated Encryption: How Subtle AEAD Differences can impact Protocol Security

Many modern security protocols such as TLS, WPA2, WireGuard, and Signal use a cryptographic primitive called Authenticated Encryption (optionally with Authenticated Data), also known as an AEAD scheme. AEAD is a variant of symmetric encryption that additionally provides authentication. While authentication may seem to be a straightforward additional requirement, it has in fact turned out to be complex: many different security notions for AEADs are still being proposed, and several recent protocol-level attacks exploit subtle behaviors that differ among real-world AEAD schemes. We provide the first automated analysis method for protocols that use AEADs that can systematically find attacks that exploit the subtleties of the specific type of AEAD used. This can then be used to analyze specific protocols with a fixed AEAD choice, or to provide guidance on which AEADs might be (in)sufficient to make a protocol design secure. We develop generic symbolic AEAD models, which we instantiate for the Tamarin prover. Our approach can automatically and efficiently discover protocol attacks that could previously only be found using manual inspection, such as the Salamander attack on Facebook’s message franking, and attacks on SFrame and YubiHSM. Furthermore, our analysis reveals undesirable behaviors of several other protocols