[messaging] key validation rules for today

elijah elijah at riseup.net
Sun Sep 7 23:50:36 PDT 2014

The threads here on key validation have been quite productive, but many
of the new email projects have need for some actual rules we can
implement in the here and now [1]. Most of these projects plan to
implement some form of TOFU, but there are many ways this could be done
and many ways this could transition to better key validation in the future.

Here is a draft text for some basic rules to navigate this transition.


That link is live editable. Please comment, edit, deplore, or applaud as
you see fit. The full text is also included below for your convenience.


[1] https://github.com/OpenTechFund/secure-email

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Transitional rules for automated key validation


Although many interesting key validation infrastructure schemes have
been recently proposed, it is not at all clear what someone writing
secure email software today should do. In particular, most of the new
opportunistic encrypted email projects have proposed starting with some
sort of Trust On First Use, but there are many ways to implement TOFU
and many ways TOFU can interact with whatever more advanced schemes are
adopted in the future.

This document attempts to specify generic rules for automatic key
management that can form a basis for proper TOFU and to transition from
TOFU to more advanced forms of key validation. In particular, the rules
try to define when a user agent should use one public key over another.
These rules are agnostic concerning what form these future systems of
key validation take.

For systems that enforce a single channel for discovery and validation,
these rules are not useful. This document is only useful for the messy
situation we find ourselves in at the present time: there is a large gap
between what systems should do now in order to be immediately useful in
the current OpenPGP ecosystem and what should be done in the future.

This document is written from the point of view of Alice, a user who
wants to send an encrypted email to Bob, although she does not yet have
his public key.

We assume:

* The goal is to automate the process of binding an email address to a
public key (we don't care about real identities).
* Alice knows Bob's email address, but not his public key.
* Alice might be initiating contact with Bob, or he might be initiating
contact with her.
* Bob might use an email provider that facilitates key discovery and/or
validation in some way, or he might not.

Unless otherwise specified, "key" in this text always means "public key".


* key manager: The key manager is a trusted user agent that is
responsible for storing a database of all the keys for the user,
updating these keys, and auditing the endorsements of the user's own
keys. Typically, the key manager will run on the user's device, but
might be running on any device the user chooses to trust.

* key directory: An online service that stores public keys and allows
clients to search for keys by address or fingerprint. A key directory
does not make any assertions regarding the validity of an address + key
binding. Existing OpenPGP keyservers are a type of key directory in this
context, but several of the key validation proposals include new
protocols for key directories.

* key discovery: The act of encountering a new key, either inline the
message, via URL, or via a key directory.

* key validation level: the level of confidence the key manager has that
we have the right key for a particular address. For automatic key
management, we don't say that a key is ever "trusted" unless the user
has manually verified the fingerprint.

* key registration: the key has been stored by the key manager, and
assigned a validation level. The user agent always uses registered keys.
This is analogous to adding a key to a user's keyring, although
implementations may differ.

* key endorser: A key endorser is an organization that makes assertions
regarding the binding of username at domain address to public key,
typically by signing public keys. When supported, all such endorsement
signatures must apply only to the uid corresponding to the address being

* binding information: evidence that the key manager uses to make an
educated guess regarding what key to associate with what email address.
This information could come from the headers in an email, a DNS lookup,
a key endorser, etc.

* verified key transition: A process where a key owner generates a new
public/private key pair and signs the new key with a prior key. Someone
verifying this new key then must check to see if there is a signature on
the new key from a key previously validated for that particular email
address. In effect, "verified key transition" is a process where
verifiers treat all keys as name-constrained signing authorities, with
the ability to sign any new key matching the same email address. In the
case of a system that supports signing particular uids, like OpenPGP,
the signatures for key transition must apply only to the relevant uid.

* endorsement key: The public/private key pair that a service provider
or third party endorser uses to sign user keys.

Key manager rules

(1) first contact: When a new key is first discovered for a particular
address, the key the highest validation level is registered.

(2) regular refresh: All keys are regularly refreshed to check for
modified expirations, or new subkeys, or new keys signed by old keys
(precisely how updates work is out of scope of this document).

(3) key replacement: A registered key MUST be replaced by a new key in
one of the following situations, and ONLY these situations:

   (a) verified key transitions (when the new key is signed by the
       registered key for same address).

   (b) If the user manually verifies the fingerprint of the new key.

   (c) If the registered key is expired or revoked and the new key is
       of equal or higher validation level.

   (d) If the registered key has never been successfully used and the
       new key has a higher validation level.

Previously registered keys must be retained by the key manager, for the
purpose of signature authentication. These old keys are never used for
sending messages, however. Keys older than X may be forgotten.

A public key for Bob is considered "successfully used" by Alice if and
only if Alice has both sent a message encrypted to the key and received
a message signed by that key.

In practice, a key manager likely will implement rule 1 by trying every
possible validation and discovery method it supports, from highest level
to lowest, until it first gets a key and then it will stop.

Validation levels

Listed from lowest to highest validation level.

1. weak-chain

Bob's key is obtained by Alice from a non-auditable source via a weak
chain. By weak chain, we mean that the chain of custody for "binding
information" is broken. In other words, somewhere a long the way, the
binding information was transmitted over a connection that was not

This form of key validation is very weak, and should either be forbidden
by the key manager or phased out as soon as practical.


Alice initiates key discovery because she wants to send an email to Bob.
Alice queries the OpenPGP keyservers for an address that matches Bob's.
This is a weak chain because anyone can upload anything to keyservers.

Bob initiates key discovery by sending Alice an email that is signed,
but Bob's email provider does not support DKIM. Alice takes the
fingerprint from the signature and queries the OpenPGP keyservers to
discover the key. This is a weak chain because there is nothing to stop
anyone from sending an email that impersonates Bob with a fake "From"
header and fake signature.

2. provider-trust

Alice obtains binding information for Bob's key from Bob's service
provider, via a non-auditable source over a strong chain. By strong
chain, we mean that every connection in the chain of custody for
"binding information" from Bob's provider to Alice is authenticated.

To subvert "provider-trust" validation, an attacker must compromise
Bob's service provider or a certificate authority (or parent zones when
using DNSSEC), but it also places a high degree of trust on service
providers and CAs.


Bob initiates key discovery by sending Alice an email that is signed by
Bob, and there is a valid DKIM signature from the provider for the
"From" header. Alice takes the fingerprint from the signature and
queries the OpenPGP keyservers to discover the key. This is
"provider-trust" because the DKIM signature binds the sender address to
the fingerprint of Bob's key, and presumably Bob authenticated with his
service provider. This also assumes Alice's user agent is able to
securely discover the DKIM public key for Bob's provider.

Alice initiates key discovery for Bob's address, checking webfinger or
DNS. These queries by Alice are 'provider-trust' so long as the
webfinger request was over HTTPS (and the server presented a certificate
authenticated by a CA known to Alice) or the DNS request used
DANE/DNSSEC. This relies on a reasonable assumption that if a provider
publishes keys via DNSSEC or HTTPS then the provider probably also
required some authentication from the user when the user uploaded their
public key.

Bob initiates key discovery by sending Alice an email that contains an
OpenPGP header that specifies a URL where Alice may obtain Bob's public
key. Bob's email contains no DKIM signature, so it could have been sent
by anyone. However, the URL is in a standard form such as
If the "From" header matches the domain, the URL is in a standard form,
the email address in the URL, and the HTTPS connection is authenticated,
then Alice may consider this "provider-trust." This is because,
regardless of who actually sent the email, what Alice sees as the sender
matches what the provider is queried for. All these conditions are
unlikely to be met in practice, but the example serves to illustrate the
broader point.

3. provider-endorsement

Alice is able to ask Bob's service provider for the key bound to Bob's
email address and Bob is able to audit these endorsements. Rather than
simple transport level authenticity, these endorsements are time stamped
signatures of Bob's key for a particular email address. These signatures
are made using the provider's 'endorsement key'. Alice must obtained and
register the provider's endorsement key with validation level at
'provider-trust' or higher.

An auditable endorsing provider must follow certain rules:

* The keys a service provider endorses must be regularly audited by its
users. Alice has no idea if Bob's key manager has actually audited Bob's
provider, but Alice can know if the provider is written in such a way
that the same client libraries that allow for submitting keys for
endorsement also support auditing of these endorsements. If a key
endorsement system is not written in this way, then Alice's key manager
must consider it to be the same as "provider-trust" validation.

* Neither Alice nor Bob should contact Bob's service provider directly.
Provider endorsements should be queried through an anonymizing transport
like Tor, or via proxies. Without this, it is easy for provider to
prevent Bob from auditing its endorsements, and the validation level is
the same as "provider-trust".

With provider-endorsement, a service provider may summarily publish
bogus keys for a user. Even if a user's key manager detects this, the
damage may already be done. However, "provider-endorsement" is a higher
level of validation than "provider-trust" because there is a good chance
that the provider would get caught if they issue bogus keys, raising the
cost for doing so.

4. third-party-endorsement

Alice asks a third party key endorsing service for binding information,
using either an email address of key fingerprint as the search term.
This could involve asking a key endorser directly, via a proxy, or
asking a key directory that includes endorsement information from a key

A key endorser must follow certain rules:

* The key endorser must be regularly audited by the key manager. Alice
has no idea if Bob's key manager has actually audited a particular key
endorser, but Alice can know if the key endorser is written in such a
way that the same client libraries that allow for submitting keys for
endorsement also support auditing of these endorsements. If a key
endorsement system is not written in this way, then Alice's key manager
must consider it to be the same as "provider-trust" validation.

* The key endorser must either require verified key transitions or
require that old keys expire before a new key is endorsed for an
existing email address. This is to give a key manager time to prevent
the user's service provider from obtaining endorsements for bogus keys.
If a key endorsement system is not written in this way, Alice's key
manager must consider it to have the same level of validation as

5. third-party-consensus

This is the same as third-party endorsement, but Alice's user agent has
queried a quorum of third party endorsers and all their endorsements for
a particular user address agree. A variant of this could be "n-of-m"
validation, where Alice's user agent requires 'n' endorsements from a
set of 'm' endorsers.

6. historical-auditing

This works similar to third-party-endorsement, but with better ability
to audit key endorsements. With historical auditing, a key endorser must
publish an append-only log of all their endorsements. Independent
"auditor" agents can watch these logs to ensure new entries are always
appended to old entries.

The benefit of this approach is that an endorser is not able to
temporarily endorse and publish a bogus key and then remove this key
before Alice's key manager is able to check what key has been endorsed.
The endorser could try to publish an entire bogus log in order to
endorse a bogus key, but this is very likely to be eventually detected.

As with other endorsement models, the endorsement key must be
bootstrapped somehow using a validation level of "provider-trust" or

7. known-key

Bob's key has been hard-coded as known by the software (mostly this just
applies to keys belonging to established endorsers, not user keys).

8. fingerprint

Alice has manually confirmed the validity of the key by inspecting the
full fingerprint or by using a short authentication string with a
limited time frame. For extra whimsy, fingerprint inspection should take
the form of a poem.

Future specification

These are out of scope for the specific problem of key validation, but
these are important issues that need to be addressed when transitioning
to opportunistic encrypted email over time.

Issuing new keys

As these rules are written, if Alice loses her private key but still has
access to her email account, she will not be able to send signed mail or
receive encrypted mail until the expiration date on the key (assuming
all the clients respect the key expiration date).

For example, imagine Alice loses access to her private key but the key
will not expire for another month. She can still authenticate with her
service provider, so she can still issue new keys and have the service
provider endorse them, or some other party endorse them. But, no valid
client should use them yet until her lost key expires.

Effectively, the primary key's expiratation date is the window of time
that Alice is willing to put up with being locked out of using encrypted
email. This window is also the same length of time that Alice has of
detecting, by audit, a provider that is publishing bogus keys for her
(before those keys potentially start to get used). So, if Alice wants
high convenience, she can set this window to be short. If Alice wants
higher security, she can set this window to be long.

At this point, it is unclear what a good value for key  expiration
should be for users who want higher convenience and for users  who want
higher security.

If a key expiration date is too soon, then there is a possibility that
Alice's key manager will not have had the opportunity to extend the key
expiration (for example, perhaps Alice is traveling and does not check
email for several weeks). Alice can still recover, since a key can still
have its expiration date extended after the key has expired, but this is
still not ideal. Alice should be able to indicate that she is
confortable with the provider always being able to issue new keys on her
behalf. It would be impractical to set the key expiration to always be
one day in the future. As a refinement, a future protocol should support
a special date annonation on a public key that says "brand new keys may
be accepted for this address after this date". If this annotation is
present, the expiration date is then only used to determine the point in
time after which a key should not be used, not the cutoff for accepting
replacement keys.

Updating keys

For high usability, a key manager will need to frequently update keys by
querying a key directory or the original source of the key. Every key
validation proposal has a different mechanism for this. The important
thing is that Alice's key manager should not make queries in a manner
that leaks Alice's addressbook to the key directories. As one example,
the program parcimonie will slowly update keys, one at a time, from
traditional OpenPGP keyservers over Tor. Also, because these updates
need to happen frequently, the key manager should have some way to first
test to see if a key is modified before downloading the full key (using
something like an etag).

Sending email

To avoid encrypted email being sent to people who no longer use OpenPGP,
the user agent should not opportunistically encrypt outgoing mail to a
recipient unless the recipient has positively indicated they wish to
receive encrypted email. Such indication may include: a signed email
message, a public key as an attachment, an OpenPGP header, a key
published by the provider or key directory (but NOT a HKP keyserver), or
when the user performs manual fingerprint verification.

When Alice sends an email with an opportunistic mail user agent, the
agent should always try to indicate that Alice prefers encrypted email.
This could be done by signing every message, although that can raise
security issues as well.

Receiving email

As alluded to above, an opportunistic mail user agent that receives a
message from a provider that does not support DKIM signatures on the
>From header should be cautious when using the OpenPGP signature or
OpenPGP header to discover and register the sender's public key. These
emails are easily spoofed by anyone on the internet, causing the user
agent to register impostor keys.

Device keys and subkeys

It would be highly desirable for all projects that use OpenPGP to
support device keys. The idea is that a user might have multiple
devices, with different keys for each device (instead of needing to
synchronize the same private key to all their devices). How might this work?

If Bob's master key has multiple subkeys with (E)ncryption usage for the
uid in question, then Alice should encrypt the message to ALL those
subkeys when sending email to Bob.

A system using subkeys like this still requires a single master key. It
may be desirable for a key validation protocol to allow for a single
email address to be bound to multiple master public keys, although this
is not supported with the current rules in this document.

Phasing out

Ideally, there should be some mechanism to phase out lower forms of
validation as higher forms become more common. In particular, it would
be good to forbid weak-chain validation entirely.

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