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Curt Tudor
Curt Tudor

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Bootstrapping Trust Part 1

Whether you are an encryption expert or a newcomer, welcome! This series is for you! It assumes you know nothing and takes you from soup to nuts on how to bootstrap trust with the intent to power a Zero Trust security model. The process and thinking described in this series are the direct output of developing the same system for the Ziti open source project. Ziti can be found on the GitHub project page for OpenZiti. The series starts with the basics and dovetails into Ziti's Enrollment system.

The parts are as follows.

Zero Trust

This entire series assumes some familiarity with Zero Trust. If you do not have a strong background in it, that is fine. This section should give the reader enough context to make use of the entire series. If a more in-depth understanding is desired, please consider reading Zero Trust Networks: Building Secure Systems in Untrusted Networks by Evan Gilman.

Zero Trust is a security model that requires strict identity authentication and access verification on every connection at all times. It sets the tone for a system's security to say, "this system shall never assume the identity or access of any connection." Before the Zero Trust security models, IT infrastructures were set up as a series of security perimeters. Think of as a castle with walls and moats. The castle would have a set number of entry points with guards. Once past the guards and inside the castle, any visitors were trusted and had access to the castle. In the real world, passing the guards is analogous to authenticating with a machine or, at worst, connect the office network via WiFi or ethernet cable.

Zero Trust does away with the concept of having a central castle that assumes anyone inside is trusted. It assumes that the castle has already been breached. That is to say, we expect attackers to already be inside the network and for it to be a hostile environment. Any resources inside the network should be treated as being publicly available on the internet and must be defended. To accomplish this defense, a series of Zero Trust pillars are defined:

  • Never Trust, Verify - the virtue of a connection should not grant access
  • Authenticate Before Connect - authentication should happen before resources are connected to
  • Least Privileged Access - access should only grant connectivity to the minimum number of resources

Implementing those pillars is not a simple tweak to existing infrastructure. The first point alone will have much of this series dedicated to it.

Ziti & Zero Trust

In a Zero Trust model, there needs to exist mechanisms to verify identities such that trust can be granted. Zero Trust does not mean there is no trust. Zero Trust means that trust is given only after verification. Even then, that trust is limited to accessing the minimum network resources necessary. To accomplish this, we need a network that can force all connections through the following process.

  1. Authenticate
  2. Request Access To A Resource
  3. Connect To The Requested Resource

This process is not the typical connection order on a network. Most connections on a network are made in the reverse order. At first, this may seem counter-intuitive. To help make Zero Trust and bootstrapping trust a bit clearer, it helps to have a concrete system to use an example. It just so happens that the Ziti software system makes a great example!

Ziti System Diagram

In Ziti, all of the above steps require interacting with a Ziti Controller. The Ziti Controller manages the Ziti overlay network by maintaining a list of known network services, SDK clients, routers, enrollments, policies, and much more! All of these pieces working together to create a Ziti Network. A Ziti Network is an overlay network - meaning it creates a virtual network on top of a concrete network. The concrete network may be the internet, a university network, or your own home network. Whatever it is, it is referred to as the underlay network.

In the Ziti Network, all network resources are modeled as services in the Ziti Controller. All services on a Ziti Network should only be accessible via the Ziti Network for maximum effect. Network services can be made available via a Ziti Network in a variety of manners. The preferred method is embedding the Ziti SDK inside of applications and servers as it provides the highest degree of Zero Trust security. However, it is also possible to configure various overlay-to-underlay connections to existing network services via "router termination" or a particular type of application with the Ziti SDK embedded in it that specifically deals with underlay-to-overlay translations (i.e., Ziti Desktop Edge/Mobile Edge).

The Ziti Controller also knows about one or more Ziti Routers that form a mesh network that can create dynamic circuits amongst themselves. Routers use circuits to move data across the Ziti Network. Routers can be configured to allow data to enter and exit the mesh. The most common entry/exit points are Ziti SDKs acting as clients or servers.

Network clients wishing to attach to the network use the Ziti SDK to first authenticate with the Ziti Controller. During authentication, the Ziti SDK client and Ziti Controller will verify each other. Upon successful authentication, the Ziti Controller can provide a list of available services to dial (connect) or to bind (host) for the authenticated SDK Client. The client can then request to dial or bind a service. If fulfilled, a session is associated with the client and service. This new session is propagated to the necessary Ziti Routers, and the required circuits are created. The client is returned a list of Ziti Routers, which can be connected to in order to complete the last mile of communication between the Ziti overlay network and the SDK client.

This set of steps covers the pillars of the Zero Trust model! The Ziti Controller and SDK Clients verify each other. The client cannot connect to network resources or services until it authenticates. After authentication, a client is given the least privilege access allowed by only being told about and only being able to dial/bind the authenticated identity's assigned services. It is a Zero Trust overlay network!

How did this system come into existence? How do the Ziti SDK client and Ziti Controller verify each other? How do the routers and controller know to validate each other? How is this managed at scale with hundreds of Ziti Routers and thousands of Ziti SDK clients? It seems that this is a recursive problem. To terminate the recursion, we have to start our system with a well-defined and carefully controlled seed of trust.


In software systems that require network connectivity, there are at least two parties in the system. Generally, there are more, and in the case of a Ziti network, there could be thousands. Between two parties, each time a connection is made, a trust decision is made. Should this connection be allowed? Mechanisms must be put into place to verify the identity of the connecting party if that question is to be answered.

One mechanism that might jump out at the reader is a password or secret. In Ziti, it would be possible to configure the Controller, Routers, and SDK Clients with a secret. Software is easy to deploy with a secret. Throw it into a configuration file, point the software at, and off you go!

It is also fundamentally weak as there is only one secret in the system necessary to compromise the entire system. In Ziti, this would mean giving the secret to network clients that may or may not be owned by the network operator. Also, shared secrets do not individually identify each component, nor do they define how secrets will power other security concerns, like encryption.

The solution can be improved. Secrets could be generated per software component. The controller, each router, and each SDK client could have a unique secret. This secret would then individually identity each component! It is a significant improvement, but how does each component verify connections? Do they challenge for the incoming connections secret and compare it to a list? That means that a pair of systems that need to connect must have each other's secrets. Secret sharing will not do! We can not be copying secrets between every machine. One machine that is compromised would mean that many secrets are revealed!

This solution can be evolved and improved, but we do not have to do that hard work! If we did, we would end up recreating an existing technology. That technology is (public-key cryptography)[\_cryptography\], and it provides everything we need.

Public-key cryptography allows each device to have a unique, secret, private key that proves its unique identity. That private key is mathematically tied to a public key. The public key can be used to encrypt messages that only the private key holder can decrypt. Also, the public key cannot be used to derive the original private key. This functionality fits perfectly with what our distributed system needs! Alas, public-key cryptography introduces complex behaviors, setup, and management. In the next article, we will dive a little deeper into this topic. For now, let us take it on faith that it will serve our needs well.

Setting It Up

So we have decided that public-key cryptography is the answer. What does that mean? What do I have to do? Let us explore what would need to be done by a human or a piece of software automating this process. Don't worry if you don't get all of this; the gist is all you need for now. Later articles will expand upon this terminology. In fact, after reading the later articles, consider revisiting this part.

Consider the following diagram of a "mesh" distributed system. This mesh could be any type of system such as a mesh of Ziti Routers, or maybe it is a system of sensors on an airplane. What they do does not matter. What matters is that this system has multiple pieces of software connecting amongst themselves. Consider what it means to accomplish this using public-key cryptography.

In the diagram above, each system needs:

  • a key pair for client and server connections
  • to have the public keys of each system it is connecting to

So what do we need to do? Drop into a CLI and start generating keys on each machine. Do that by using these commands:

openssl ecparam -name secp256k1-genkey -param_enc explicit -out private-key.pem

openssl req -new -x509 -key private-key.pem -out server.pem -days 360

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Voila - you now have a self-signed certificate! What is a self-signed certificate? For now, let us understand it means that no other system has expressed trust in your public certificate. In Part 4: Certificate Authorities & Chains Of Trust we will cover them in more detail.

You can repeat the above process for every piece of software in your mesh network. Preferably, you log into each machine and generate the private key there. Moving private keys on and off devices is a security risk and frowned upon. For maximum security, hardware, such as Hardware Security Modules (HSMs) and Trusted Platform Modules (TPMs), can be used to store the private keys in a manner that does not make them directly accessible.

Then you will need to copy each public certificate to every other machine and configure your software so that it trusts that certificate. The system will need to repeat this process any time the system adds a piece of software. If a machine is compromised, the analogous public certificate will need to be untrusted on every node in the mesh. Adding or removing trust in a public certificate involves configuring software or operating systems. There are many ways it can be implemented, including configuration files, files stored in specific directories, and even via configuration tools such as Windows Certificate Manager snap-in.

This is a log of careful work to get a simple system running. Consider what this means when adding or removing many nodes? Visiting each machine and reconfiguring them each time is quite a bit of overhead. There is a solution to these woes. While it is elegant on its own, it does add complexity. Let us see how Certificate Authorities (CAs) can help! In the next section, we will hit the highlights of CAs. For more detail, look forward to Part 4: Certificate Authorities & Chains Of Trust.

CAs & Adding Complexity

A CA enables trust deferral from multiple individual certificates to a single certificate, which means that instead of trusting each certificate, each piece of software will trust the CA. The CA will be used to sign every public certificate our software pieces need to use. How does "signing" work? We will cover that in part three and why it matters part in four. For now, the basics will be provided.

Here are the high-level steps of using a CA:

  1. create a CA configuration via OpenSSL CNF files
  2. create the CA
  3. use the CA's public key to sign all of the public certificates
  4. distribute the CA's certificate to every machine
  5. configure the machines certificate store or configure the software

For items one and two, the process can be a bit mystical. There is a multitude of options involved in managing a CA. To perform number three, you will need to go through the processing of creating certificate signing requests (CSRs, see parts three for more detail) on behalf of the piece of software, and someone or something will have to play the role of the CA and resolve the CSRs. The last two steps will depend on the operating system and software being used.

All of these actions can be done via a CLI or programmatically. You will have to spend time and energy, making sure the options are correctly set and learning about all the different capabilities and extensions. Mistakes will inevitably occur. It is time-consuming to debug why a specific public certificate is not working as intended. The tools and systems that use the certificates are purposely vague in error messages as not to reveal too much information to attackers.

The payoff for using CAs is having the ability to create chains of trust. Chains of trust allow distributed systems to scale without having to reconfigure each node every time the system grows or shrinks. With a little more upfront cost and bookkeeping to run a CA, the system will greatly decrease the amount of configuration required on each device.

Further Concerns

Once configured, there are still other concerns that need to be taken into account. Consider the following list of events that may happen to a CA, and it's certificates:

  • What happens when a certificate expires?
  • How does a system know not to trust a certificate anymore?
  • What happens when private keys need to regenerate?

CAs do not automatically handle the propagation of these types of events. CAs are files on a storage device or HSM. Issuing or revoking certificates does not generate any kind of event without additional software. There is also the issue of certificates expiring. That "-days 360", used in the example above, puts a lifetime on each certificate. The lifetime can be extended far into the future, but this is a bad practice. Limiting the life span of a certificate reduces attack windows and can be used as a trigger to adopt strong encryption.

Even if we ignore all of those concerns, who did we trust to get this system setup? What was the seed of trust used to bootstrap trust? So far, you could have imagined that a human was doing all of this work. In that case, a human operator is trusted to properly configure all of the systems - trusting them with access to all of the private keys. The seed of trust is in that human. If this is a software system performing these actions, that means that the system has to be trusted and most likely have access to every other system coming online. That is workable, but what happens when your system can have external systems request to be added to the network? How can that be handled? How do you trust that system in the first place? Using a secret password creates a single, exploitable, weak point. Public-key cryptography could be put in place, but then we are in a chicken-and-egg scenario. We are putting public-key cryptography in place to automate public-key cryptography.

There are many caveats to bootstrapping trust. In a dynamic distributed system where pieces of software can come and go at the whim of network operators, the issues become a mountain of concerns. Thankfully in Ziti, a mechanism is provided that abstracts all of these issues. To understand how Ziti accomplishes this, we have a few more topics to discuss. In part two, we will chip away at those topics by covering public-key cryptography in more detail to understand its powers and applications.

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