With the release of Rails 5.2 and the changes with how secrets are securely stored, I thought it would be timely to write about the benefits and downsides of secrets management in Rails. It would be valuable to compare how Rails handles secrets, how Shopify handles secrets, and a few other methods from the open source community. On my journey to write about this I got caught up in explaining how symmetric and public key encryption work. So the post comparing different Rails secret management gems will have to wait until another post.

Managing secrets is now more challenging

A majority of applications created these days integrate with other applications – whether it’s for communicating with other business-critical systems, or purely operational such as log aggregation. Secrets such as usernames, passwords, and API keys are used by these apps in production to communicate with other systems securely.

The early days of the Configuration Management, and then later the DevOps movements have rallied and popularized a wide array of methodologies and tools around managing secrets in production. Moving from a small, artisanal, hand-crafted set of long-running servers to the modern short-lifetime cloud instance paradigm now requires the discipline to manage secrets securely and repeatedly, with the agility to revoke and update credentials in a matter of hours if not minutes.

Reactions to a rare human initiated deploy at @shopify pic.twitter.com/l4eO5wrsMr

— Camilo Lopez (@camilolopez) October 31, 2017

While there’s many ways to handle secrets while developing, testing, and deploying Rails applications, it’s important to bring up the benefits and downsides to the different methods, particularly around production. Different levels of security, usability, and adoption exist with different technologies. Public/private key encryption, also known as RSA encryption, is one of the technologies. Symmetric key encryption is also another common encryption technology.

There exist many ways to handle secrets within Rails and webapps in general. It’s important to understand the underlying concepts before settling on one method or another because making the wrong decision may result in secrets being insecure, or the security being too hard to use.

Let’s first discuss the different types of encryption that are characteristic of the majority of secret management libraries and products out there.

Symmetric Key Encryption

Symmetric key encryption may be the simplest form of encryption to understand, but don’t let that trick you into thinking that it’s not secure. Symmetric key encryption involves one key used to both encrypt and decrypt data. This key will have to be kept secret and only be shared with trusted people and systems. Once secrets are encrypted with the key, that encrypted data can be readily shared and transferred without worry of the unencrypted data being read.

A simple example of symmetric key encryption can be explained. The most straightforward method utilizes the binary XOR function. (This example is not representative of state of the art symmetric key encryption algorithms in use, but it does get the point across). The binary XOR function means “one or the other, but not both”. Here is an example that shows the complete set of inputs and outputs for one binary digit:

1 XOR 1 = 0
1 XOR 0 = 1
0 XOR 1 = 1
0 XOR 0 = 0

A more complicated example would be:

10101010 XOR 01010101 = 11111111
11111111 XOR 11111111 = 00000000
11111111 XOR 01010101 = 10101010

Note that line 1 and 3 are related. The output of line 1 is part of the input of line 3. The second parameter of line 1 is used as the second parameter of line 3 too. Notice that the output of line 3 is the same as the first input of line 1. As demonstrated here, the XOR function will return the same input if the result of the function is fed back into itself a second time. A further example will show this property.

Given the property that any higher form of data representation can be broken down to binary, we can then show the example of hexadecimal digits being XOR’ed with another parameter.

12345678 XOR deadbeef = cc99e897

Given the key is the hexadecimal characters deadbeef and the data to be encrypted is 12345678, the result of the XOR is the incomprehensible result cc99e897. Guess what? This cc99e897 is encrypted. It can be saved and passed around freely. The only way to get the secret input (ie. 12345678) is to XOR it again with the key deadbeef. Let’s see this happen!

cc99e897 XOR deadbeef = 12345678

Fact check it yourself if you don’t believe me, but we just decrypted the data! This is the simplest example of course, so there’s a lot more that goes into symmetric key encryption that keeps it secure. Things like block-based, and stream-based algorithms, and even larger key sizes augment the simple XOR algorithm to make it more secure. It may be simple for someone who wants to break the encryption to guess the key in this example, but it becomes much harder the longer the key size is.

This is what makes symmetric key encryption so powerful – the ability to encrypt and decrypt data with a single key. With this property comes the need to keep this single key secret and separate from the data. When symmetric key encryption is used in practice, the smaller amount of people and systems that have the key the better. Humans can easily lose the key, leave jobs, or worse: share the key with people of malicious intent.

Public Key Encryption

Quite opposite to how symmetric key encryption works, public key encryption, (or asymmetric key encryption, or RSA encryption) uses two distinct keys. In its simplest form the public key is used for encryption and the private key is used for decryption. This method of encryption separates the need for the user who is encrypting the data from having the ability to decrypt the data. Put plainly, it allows for anyone to encrypt data with the public key while the owner of the private key is the only one able to decrypt the data. The public key can be shared with anyone without compromising the security of the encrypted data.

Some tradeoffs between symmetric and public key encryption is that the private key (the key used to decrypt data) is never shared with other parties, whereas the same key is used in symmetric key encryption. Also, a downside of public key encryption is that there are multiple keys to manage, therefore it brings a higher level of overhead compared to symmetric key encryption.

Let’s dig into a simple example. Given a public key (n=55, e=3) and a private key (n=55, d=27) we can show the math behind public key encryption. (These numbers were fetched from here).

Encrypting

To encrypt data the function is:

c = m^e mod n

Where m is the data to encrypt, e is the public key, mod is the modulus function, n is the shared modulus, and c is the encrypted data.

For the number 42 to be encrypted we can plug it into the formula quite simply:

c = 42^3 mod 55
c = 3

c = 3 is our encrypted data.

Decrypting

Decrypting takes a similar route. For this a similar formula is used:

m = c^d mod n

Where c is the encrypted data, d is part of the private key, mod is the modulus function, n is the shared modulus, and m is the decrypted data. Lets decrypt the encrypted data c = 3:

m = 3^27 mod 55
m = 42

And there we have it, our decrypted data is back!

As we can see, a separate key is used for encryption and decryption. It’s worth restating that this example here is very simplified. Many more mathematical optimizations, and larger key sizes are used to make public key encryption secure.

Signing – a freebie with public key encryption

Another benefit to using RSA public and private keys is that given the private key is only held by one user, that user can sign a piece of data to verify that it was them who actually sent it. Anyone who has the matching public key can verify that the data was signed by the private key and that the data was not tampered with during transit.

When Bob needs to receive data from Alice and Bob needs to be sure it was sent by Alice, as well as not tampered with while being sent, Alice can hash the data and then encrypt that hash with her private key. This encrypted hash is then sent along with the data to Bob. Bob can then use Alice’s public key to decrypt the hash and compare it to a hash of the data that he performs. If both of the hashes match, Bob knows that the data was truly from Alice and was not tampered with while being sent to him.

Wrapping up

To pick one method of encryption as the general winner at this abstract level is nonsensical. It makes sense to have a use case and pick the best encryption method for it by finding the best fit at the abstract level first, then finding a library which offers that method of encryption.

A following post will go into the tradeoffs between different encryption methods in relation to keeping secrets in Ruby on Rails applications. It will take a practical approach, explaining some of the benefits of one encryption method over another, and then give some examples of well-known libraries for each category.