Potential ecosystem dangers of Autocrypt

This document is a place to describe particular concerns that Autocrypt creates for the e-mail ecosystem as a whole. It does not address attacks against the cryptography or compromises to the message confidentiality it aims to support.

These risks may not be large risks, or they may be mitigatable in some way, but we document them here for general awareness.

In all, we currently believe that the benefits to the ecosystem of having more end-to-end message confidentiality outweigh these potential risks.

Message Deliverability

Autocrypt headers that use RSA 3072 are large enough that, when unwrapped, they exceed the SMTP line length limit of 1000 ASCII characters.

It’s conceivable that some MTAs or MUAs will choke upon trying to deal with these headers, and render the message undeliverable or unreadable. We have no evidence of this happening today (December 2016), but maybe we’re just not yet tickling the systems that have these problems.

Possible mitigations:

  • sending duplicate headers each with parts of the key data. But this makes reassembly and message-parsing logic significantly more complex, and it would be nice to not need it.

Denial of Service: malicious creation of unreadable mail

An active attacker who wants to interrupt communication between two parties can do so if they know that one party uses an Autocrypt-capable agent. Consider the case where Mallory wants to interrupt communications between Alice and Bob, and she knows that Bob uses an Autocrypt-capable MUA.

Mallory crafts a new key K. She can throw away the secret key material entirely if she wants to. She then forges an e-mail from Alice and adds an Autocrypt header to it containing that public key and prefer-encrypted=yes. If Bob writes a message to Alice after receiving that key, and before receiving any other legitimate message to Alice, his message will be encrypted to a key that Alice cannot read.

this represents a risk to Alice, even if she has never adopted an Autocrypt-capable MUA in the first place.


  • Alice’s next mail to Bob will correct Bob’s MUA’s state so that futre mails will be back to Alice’s actually preferred state. So the attacker must sustain a series of forgeries if the denial of service attack is intended to be sustained.
  • we should specify that any spam/malware flag set from a filter that the user trusts should be sufficient to discourage processing of Autocrypt headers, so that Mallory needs to craft a sufficiently-plausible message (including DKIM and whatever other indicators the filters care about) to make it into the Autocrypt-capable MUA’s internal state storage.

Killing off strong encryption

Autocrypt is significantly weaker than traditional models of mail encryption. In particular, it provides no resistance to an active attacker (an attacker who can modify and/or inject mail as it passes through the SMTP network). The no-UI feature makes it so that most users will never properly verify each other’s encryption keys.

There is a concern that if opportunistically-encrypted mail becomes the standard, no one will bother to implement good UX for users in strong identity verification.


  • make out-of-band verification of keys between users fun and thus increase the risk for attackers to get detected.
  • research how “level 2” Autocrypt could evolve to offer automated support against active attackers.

A note on Autocrypt and provider spam/malware filters

Mike Hearn raised some fundamental concerns in his Modern anti-spam and E2E crypto post on the modern crypto mailing list on how end-to-end encrypted mails and spam infrastructure possibly interfere. While we may conceive new ways to fight spam in an E2E setting by increased DKIM usage and other additional measures the topic is a serious one as adoption of more encrypted mails could be seriously hampered if encryption can bypass current anti-spam technology.

Autocrypt works with existing provider Anti-Spam infrastructures because they can continue to check the initial cleartext mails for suspicious content. Only if a user replies to a (likely non-spam) mail will Autocrypt make a MUA send an encryption key. Without being able to get sufficiently many replies from users it will likely be to massively harvest encryption keys; there is no central registery for key-mail address relations. Massive collection of key/mailaddress associations would require co-operation from or compromise of big mail providers which is unlikely given they have been fighting unsolicited mails for decades and their business models depend on it.