Dear all,

I wanted to point out a preprint we recently put on the arXiv, which seems 
potentially relevant to the Autocrypt project, on more 
metadata-privacy-preserving encoding techniques for encrypted data blobs like 
those PGP produces:

        Reducing Metadata Leakage from Encrypted Files and Communication with 
PURBs
        https://arxiv.org/abs/1806.03160 <https://arxiv.org/abs/1806.03160>

The idea is to ensure that the encoding leaks no metadata at all other than via 
length - including cyphers used, number and identities of receivers, etc. - and 
leaks as little as possible even via the length, while still ensuring 
efficiency (e.g., ensuring receivers don’t need to do an exhaustive scan 
through a markerless stream of random bits).  This could help protect users 
against a variety of potential attacks, such as:

- An attacker, who can passively monitor the plaintext E-mail between only two 
members of a group, learning how many total members in the group there are 
(i.e., to how many recipients the blob is encrypted), and/or perhaps learning 
something about the identities of those recipients.
- An attacker learning from the unencrypted PGP header metadata exactly which 
PGP software implementation and version the sender is using, which 
ciphersuites, etc., by fingerprinting the exact structure of that metadata, as 
a cheap way of monitoring passively for senders who might be using old versions 
of encrypted software with known, exploitable vulnerabilities.

In short, by PURB-encoding encrypted blobs instead of using the traditional PGP 
wrapper, we can guarantee that everything in the E-mail that “looks” random and 
encrypted in the message (i.e., everything in the base64-encoded blob) actually 
*is* encrypted and provably leaks as little as possible information of any kind 
to any passive attacker.

We’d love to see the ideas in this paper eventually get into a next-generation 
E-mail standard like Autocrypt, and would be happy to help make it happen if 
there’s interest.  Thoughts/feedback welcome.

Thanks
Bryan

Abstract:
Most encrypted data formats, such as PGP, leak substantial metadata in their 
plaintext headers, such as format version, encryption schemes used, the number 
of recipients who can decrypt the data, and even the identities of those 
recipients. This leakage can pose security and privacy risks, e.g., by 
revealing the full membership of a group of collaborators from a single 
encrypted E-mail between two of them, or enabling an eavesdropper to 
fingerprint the precise encryption software version and configuration the 
sender used and to facilitate targeted attacks against specific endpoint 
software weaknesses. We propose to improve security and privacy hygiene by 
designing future encrypted data formats such that no one without a relevant 
decryption key learns anything at all from a ciphertext apart from its length - 
and learns as little as possible even from that. To achieve this goal we 
present Padded Uniform Random Blobs or PURBs, an encrypted format functionally 
similar to PGP but strongly minimizing a ciphertext's leakage via metadata or 
length. A PURB is indistinguishable from a uniform random bit-string to an 
observer without a decryption key. Legitimate recipients can efficiently 
decrypt the PURB even when it is encrypted for any number of recipients' public 
keys and/or passwords, and when those public keys are of different 
cryptographic schemes. PURBs use a novel padding scheme to reduce potential 
information leakage via the ciphertext's length L to the asymptotic minimum of 
O(log2(log2(L))) bits, comparable to padding to a power of two, but with much 
lower padding overhead of at most 12%which decreases further with large 
payloads.

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