A High-Level overview of OpenPGP CA

OpenPGP CA is two things:

  1. It's a paradigm (a set of best practices) for how to use OpenPGP in organizations or groups.

  2. And, it's tooling to more easily apply this paradigm in practice.

One of the most important aspects of secure communication is making sure that your message goes to the right person and that messages you receive actually came from the person they claim to. This is authentication - and the core of what OpenPGP CA deals with. The OpenPGP CA paradigm for how to handle authentication greatly simplifies authentication for users and makes it commonplace.

For many use cases, it's indispensable to establish authentication before using encryption. Using encryption on an unauthenticated communication channel is risky - we can't tell if our communication is secure.

OpenPGP CA introduces tooling that an admin can use to record organizational knowledge in a form that OpenPGP software already understands. For instance, Alice Adams' email address is alice@example.org and this is a copy of her OpenPGP public key. This is the authentication aspect.
The tooling also facilitates key discovery, by making it easy for the admin to publish keys in places that OpenPGP software normally looks for them (e.g. WKDs and key servers). And, it makes it easier to keep those directories up to date. Finally, OpenPGP CA simplifies managing keys by storing revocation certificates, and making it easy to publish one, if and when that is necessary.

OpenPGP CA works with existing OpenPGP software. OpenPGP is an encryption and digital signing standard, which is often used with email. The other widely used email encryption standard, which OpenPGP CA does not deal with, is S/MIME.
There are many implementations of OpenPGP. The most well known implementation is GnuPG, but there is also OpenPGP.js and Sequoia PGP, which OpenPGP CA uses internally.

How OpenPGP gets introduced to organizations

Anecdotal evidence suggests that OpenPGP is often introduced to an organization by a technically competent person who recognizes a need for secure communication. That person then convinces everyone to adopt OpenPGP. They organize a briefing (which is sometimes called a CryptoParty), and teach everyone how to generate a key, how to do key discovery, how to certify keys, etc. When done well, the members of the organization learn what they need to do to communicate securely.

But, even in the best cases, most users often only have a superficial understanding of what they need to do, and the technical leader needs to provide them with intense support. And, due to the high overhead, authentication is often neglected based on the perception that "usually we will find the correct key in some kind of ad-hoc manner, anyway."

Authentication

The overarching goal of OpenPGP CA is that users can be certain they are using the correct OpenPGP keys for their communication partners. This is called authentication: ascertaining that a key is indeed the correct key for the other party. (A closely related goal is key discovery, which OpenPGP CA also simplifies.)

Imagine that we're receiving an email from Alice. Our email software can indicate to us whether we can authenticate Alice's OpenPGP key.

For example, the Enigmail plug-in for Thunderbird 68 shows the authentication status for a signed email with two visual cues: 1) the color of the bar at the top of the email window, and 2) the envelope icon at the right side of the window.

This is how an email looks from an unauthenticated sender:

Image

In contrast, when authentication works, Thunderbird/Enigmail shows this with a green bar, and a wax seal on the envelope icon, both indicating that we have an authenticated key for Alice:

Image

More precisely, what is authenticated is the association between an identity and a key. Authentication deals with identities and asserts that there is reason to believe that a key in question is indeed controlled by a certain identity.

If we want to be sure that an identity associated with a key is correct, we need to perform steps to authenticate that key. A traditional method to authenticate a key with OpenPGP is to have the owner communicate the fingerprint of that key. We might get it in person - asking the owner to confirm that the fingerprint we have is the correct one. Or, the person might have given us a business card that includes their fingerprint. These approaches are time consuming, and often not possible (what if you never meet the person in real life?). OpenPGP CA simplifies authentication by non-exclusively delegating that task to a trusted party.

The importance of authentication

When we obtain an OpenPGP key that claims to belong to Alice from an untrusted source, we cannot be sure if the key is indeed controlled by Alice, and not by some malicious party.

This is a problem, because a malicious party could perform various types of attacks, including:

  • send us a seemingly correctly signed email (which might lead to false confidence in the origin of a piece of email - such attacks are called phishing or spear-phishing), or

  • intercepting our attempts to securely communicate with Alice through an encrypted channel ("man-in-the-middle attack").

With OpenPGP CA the most common communication partners are automatically authenticated

We can classify communication partners into three categories: people in the same organization, people in an affiliated organization, and other. For our purposes, we consider two organizations to be affiliated if they often communicate with each other. OpenPGP CA is designed to secure the first two types of communication, but it can even help with the third type.

The following figure shows two affiliated organizations, alpha.org and beta.org, a few of their members, a third-party (Carol), arrows showing who communicates with whom, and how often. These communication patterns are typtical for many organizations.

Image

Using OpenPGP CA, the admin of alpha.org and the admin of beta.org can ensure that all of their users' OpenPGP-based tools can automatically authenticate all of their communication partners. That is, after the initial setup, normal users don't need to do anything to authenticate their communication partners. The admins do all of the work with the help of OpenPGP CA.

Intended Audience

OpenPGP CA helps organizations or groups model trust relations in OpenPGP.

We use the term "organization" to refer to any group of people who might use OpenPGP CA together - whether they are an informal group, a commercial organization, or any other form - such as:

  • Journalistic organizations
  • Human rights groups
  • Informal groups of activists
  • A company or a department at a company

OpenPGP CA's approach is based on the observation that in organizations, users already trust their administrators with access to their data (including email) and the integrity of their systems. So, asking them to also maintain a directory of users and keys does not require placing additional trust in them.

Users need to learn fewer skills

Implementing any new security practice requires educating users about its operational aspects. The difficulty is making sure users are not overwhelmed, as that undermines the security goals.

Traditionally, users of OpenPGP have had to learn many technical details. These details are necessary to achieve the security goals. OpenPGP CA doesn't remove these details, but shifts them to a new actor, the OpenPGP CA admin. This greatly lessens the burden placed on normal users, who are more interested in getting their job done than understanding the technical minutiae.

Concretely, OpenPGP CA users only need to be taught a few high-level skills to get significant value from OpenPGP:

  • encrypt and sign email, as well as
  • how to recognize encrypted and signed email.

OpenPGP CA alleviates non-technical users from having to learn many low-level tasks, such as:

  • doing key discovery,
  • checking that a key belong to the intended party (authentication and certification), and
  • creating their own key.

This allows users to focus on the indispensable high-level concerns and reduces the risk of user errors.

This setup has several advantages for users. By delegating authentication to an in-house CA, the cognitive burden placed on users is significantly reduced: users don't have to compare fingerprints or even understand keys or certifications to effectively use OpenPGP. At the same time, because OpenPGP CA uses OpenPGP's existing mechanisms, users with special needs can still use other solutions, e.g., directly verifying someone's key in the customary manner.

The OpenPGP CA admin role

What is the CA admin role?

OpenPGP has traditionally been aimed at individual users, each fending for themselves. Our approach introduces the role of an "OpenPGP CA admin", a per-organization role that serves as a centralized facilitator for OpenPGP users in that organization.

The OpenPGP CA admin authenticates users within an organization, so that users within that organization are mutually authenticated. Users can use each others' OpenPGP keys with confidence - without the need to spend effort on low-level details about key discovery and authentication.

The key assumption for OpenPGP CA is that users have a common trusted party who can perform this OpenPGP CA admin role for them.

In formal organizations, this might be the existing OPSEC team. In an informal group it might be a person who volunteers for that job and is viewed by the other team members as both technically competent and trustworthy.

Trade-offs of centralizing responsibility for authentication

Users need to trust their OpenPGP CA admin to do OpenPGP authentication on their behalf. This effectively centralizes authentication, which deviates from OpenPGP's decentralized tradition. However, contrary to TLS where a third-party customarily does the authentication, users in an organization already trust their administrator.

In many cases, the OpenPGP CA admin role will be filled by the users' system administrator. In that role, the administrator already control the users' systems - and can install arbitrary software, for instance.

In other words, such an administrator is already in a position where they could undermine the integrity of users' systems in practically limitless ways.

Therefore trusting this admin to also authenticate business relationships does not change existing trust boundaries - and does not increase the organization's risk.

In short, the centralization that the OpenPGP CA admin role brings is not a significant change to users' threat models, and does not undermine OpenPGP's decentralized nature.

Risks when a CA admin makes mistakes

The role of the CA admin centralizes tasks that would otherwise be the responsibility of individual users. As described above, this brings a lot of benefits for users, however, it also introduces new, centralized risks.

One particular difficulty in deploying OpenPGP CA is that the CA admin's key needs to be well protected. If it is compromised, then an attacker is able to mark arbitrary keys as authenticated.

Apart from that, when authenticating keys, the CA admin needs to be diligent. The CA admin needs to have a good understanding of OpenPGP concepts be able to perform their tasks correctly. If the CA admin makes mistakes, users are at risk. Depending on the consequences, not using OpenPGP CA may be better than creating a false sense of security.

Comparing the OpenPGP CA admin role with CAs for TLS server certificates

The concept of a certificate authority (CA) is well known in the context of TLS server certificates, which are used for authenticated and encrypted communication on the web.

TLS certificates claim an identity (the domain name of a website). This identity is verified and cryptographically vouched for by a CA. CAs for TLS server certificates act as a group of globally trusted verifiers of identity (often, but not always, for-profit). To organizations that use TLS certificates, these CAs are external actors.

While TLS server certificates of course bring massive benefits for secure communication on the web, there are also problems:

  • The interests of CAs in the TLS space are not aligned with the interests of their users.
  • For-profit CAs are driven by profit, not by the needs of users.
  • Law enforcement might interact with these CAs in ways that are contrary (and opaque) to the users of the certificates and detrimental to their goals. CAs agree to help, because they don't want to cause trouble with law enforcement.

These risks are real. TLS CAs have been known to be sloppy and potentially malicious. And, the authentication that the CAs perform is often extremely weak.

Our main observation about TLS in this context is that it centralizes trust in untrustworthy third parties.

Interests of the OpenPGP CA admin and their users are aligned

In contrast, OpenPGP CA facilitates a decentralized, federated approach to trust and authentication. OpenPGP CA embraces OpenPGP's decentralized trust model and makes it easy to leverage its inherent benefits.

Trust management with OpenPGP CA is somewhat centralized - but only within the scope of individual organizations. The interests of the in-house CA admin are strongly aligned with the interests of the users and the organization overall.

Using OpenPGP CA does not require placing trust in an outside third party with potentially conflicting interests. This is essential for activists, journalists, and lawyers.

Bridges between organizations

OpenPGP CA cannot only be used to create authenticated paths between users in a single organization, but also between organizations, in a decentralized, federated manner.

Affiliated organizations that use OpenPGP CA can easily set up what we call a bridge between their respective CAs. Creating a bridge creates authenticated paths between all users in the two organizations - users in each organizations can authenticate keys of users in the other without any additional effort.

This makes sense when the CA admins believe that the other organization's CA admin does a good job authenticating their user's keys in OpenPGP CA.

As usual, we want to exploit existing trust boundaries. When an organization creates a bridge to another organization, the latter organization's CA admin is only trusted to authenticate users in their own organization. This is done by scoping the trust: when the CA admin from organization A authentictes the CA admin from organization B, they indicate that B should only be trusted to authenticate users in the same organization. This is done using existing OpenPGP mechanisms. Specifically, by matching on the email's domain name.

No key escrow

Centrally storing users' private key material has legitimate uses - however, it also comes with massive risks.

OpenPGP CA does not do key escrow - that is, even when OpenPGP CA generates keys for users, the private key material is never stored in the OpenPGP CA database.

Complements existing OpenPGP usage

Because OpenPGP CA works within the existing OpenPGP framework, i.e., it doesn't require any modification of existing OpenPGP software, users do not need any new software to take advantage of OpenPGP CA. Concretely, they can continue to use existing email clients and encryption plugins. Further, OpenPGP CA can co-exist with other authentication approaches like traditional key certification workflows.

OpenPGP CA can be rolled out gradually within an organization.

While OpenPGP CA prescribes some aspects of how OpenPGP keys and certifications should be handled, our approach offers some degrees of freedom, so that security specialists in organizations can tailor their use to their specific needs. That said, our framework/paradigm makes OpenPGP key management less ad-hoc and more systematic.

OpenPGP CA as tooling for the admin

OpenPGP CA vastly improves the capabilities of the administrator by giving them tooling to model existing trust relationships in their organization.

Traditionally, tooling in the OpenPGP ecosystem was mainly aimed at users. Dedicated administrators of OpenPGP setups have built ad-hoc tools for tasks they perform, but these were point solutions, and often incomplete.

The benefits of OpenPGP CA are - at least in theory - not particular to OpenPGP CA: a dedicated administrator could perform all of the relevant tasks manually. However, in practice, these tasks are so hard for administrators to perform correctly with existing tooling that no one uses this type of setup.

Is OpenPGP CA suitable for my use case?

OpenPGP CA is not for every everyone. Here are some considerations:

  • OpenPGP CA is for groups. An individual will not profit from installing OpenPGP CA, because they have no one to delegate authentication to.
  • There has to be a trusted, competent party who can perform the OpenPGP CA admin role.
    The CA admin needs to have the relevant knowledge as well as skillset, and users must trust them to do authentication on their behalf.
  • OpenPGP CA exposes the structure of the organization. For most companies, this is not a problem, because they already have employee directories. For some activist groups, this may be a problem.

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