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The thoughtbot Guide to Application Security

Threat modeling

The task of identifying concrete attacks and understanding their relationship with the code is the core task of threat modeling. We can understand this from two perspectives:

  • identify what can go wrong, and
  • don't account for things that cannot go wrong.

Identifying what can go wrong is what is most often written about when discussing threat modeling. There are many threat modeling techniques, but the summary is:

  1. Create a list of what an attacker can do on your app. For a Web app, they might be able to spoof HTTP headers, submit malicious data, or embed a Web page in an iframe.
  2. Add to the list the weak points of the app. These will likely be places where you are doing something non-standard, which the frameworks don't know how to protect.
  3. Prioritize this list. Take into account factors such as difficulty of attack, likelihood of attack, ease of mitigating the attack, and severity of attack.

Anything not in the list are things you cannot use as a reason to do something. Since the list is prioritized, you can use it to help prioritize tickets or split tickets.

Library updates

The easiest line of defense you have as a developer is applying security fixes for our dependencies as they are released.

On the flip perspective, when releasing a security fix for one of our projects, make it trivial to upgrade: don't include new features or unrelated bug fixes.

There are a few ways to keep up with security fixes:

If you have access, the thoughtbot #security channel does our best to keep up with security issues that we think will affect us or our clients.

Secure programming

In an ideal world, access to the program's source code will not give an attacker an advantage. This is not always possible, but programming with a mindset of preventing an all-knowing attacker can be healthy.

Some tips along the way:

  • Always check return values. If the procedure can raise, make sure to handle that (to prevent DoS attacks). If the procedure can signal failure, make sure to handle that (to prevent read-after-free-style attacks).
  • Fail fast. If the data seems odd, don't recover: fail.
  • Leave the most security-sensitive code as an omega mess, once it works. Too many bugs -- more than zero -- come out of refactoring to be worth a change in the name of code beauty.

User data

Any data from the user is malicious until proven innocent. Examples of user input are data from forms, HTTP headers, text the user enters into your mobile app, IP address, MAC address, email headers, file paths, GraphQL queries, uploaded files, and stdin. And more.

When possible, rely on a framework to parse user data. Don't parse HTTP headers by hand, use the Rails validations, pass JSON data through a schema validator, send addresses straight to the shipping or map API, etc.

If you can't rely on a library, handle user data in two stages: verify, then work with it. For example, if someone uploads a file with a filename ending in .jpg, use libmagic to confirm that it is a JPEG, and then consider it less tainted and ready for use.

SQL injection

We know about this one, so let's make sure it does not happen.

Whenever you run a SQL query, don't insert user input into it. If you must insert user data into it, use a bind variable. (The details of how bind variables work depends on your object-relational mapping library.)

YAML

YAML is too vulnerable to attacks to consider for new projects.

Client-side validation

All client-side validation, such as a React component that tells the user that their email address is not in a valid format, is for presentation. These checks, and more, must be duplicated on the backend. Any attacker can use curl to bypass your client-side validations.

Cookies

Cookies are user-controlled input and, therefore, should be treated with suspicion. If possible, don't rely on a cookie.

Cookies can be copied between browsers. Just because a request sends a cookie does not mean that the cookie was sent by the user's original browser. It might come from curl.

One way to retain control over the cookie data is to sign it using a secret key only known by the server. Rails does this for you.

Logging

Logging is a compromise between having enough data to be able to debug a problem and having too much personally-identifying information about a user.

Make sure not to log passwords, credit card numbers, or any other information that you do not strictly need. Err on the side of not logging any strings, if possible.

In Rails, use the filter_paramters configuration setting to remove known attributes from the logs.

In addition, if you are logging to a service over a network connection, make sure the connection itself is secured using TLS.

Personally-Identifying Information (PII)

As much as you can, do not touch any information you don't need. Some tricks for this:

  • Send any credit card data directly to the payment processor from the client. They'll give back a token, which you can store safely.
  • You probably don't need the user's sex, gender, date of birth, middle name, and so on. You might, but ask yourself first: do you?

Randomization

Most modern cryptography is dependent on really big prime numbers and access to solid randomization. If you find yourself in a place where you need a random number, here are some things to keep in mind.

  • Don't do this yourself. If you can use Ruby's SecureRandom or functions like arc4random_buf(3) and arc4random_uniform(3), do that instead.
  • Do not restrict the randomized space with a modulo or floating-point multiplication bias. Instead, try generating a random number in a loop, returning when the value is within the desired range.
  • Use an unpredictable seed. Do not use the current time, or the seconds since boot, or 0, or your age, or the result from calling rand seeded on a predictable seed. If possible, use a random number generator that you do not seed yourself, such as arc4random(4) or /dev/random.
  • Use a non-blocking random number generator. If an attacker discovers that the random number generator blocks, such as Linux's /dev/urandom, that is a potential denial of service attack vector.

Hashing

A hashing function provides a one-way encoding of an object. Use this any time you don't actually care what the value is, but instead you care that you have it at all. The only operation you'll want to perform against a hashed object is an equality check.

(As a side note, when people refer to dictionary data structures as "hashes", they're referring to the fact that a hashing function is used to turn the key into a unique number.)

(As a second side note, when people refer to blockchains as "cryptocurrency", they're making reference to the fact that they used a hashing function. Twice.)

Hashing algorithms are as strong as their ability to generate a unique, one-direction hash. When someone finds a way to generate the same hash for two different inputs, the hashing function is considered insecure. The American National Institute of Standards and Technology (NIST) maintains a list of approved hash algorithms; as of this writing SHA-2 and SHA-3 are approved.

Note that base64 encoding is not a hashing function, since it intentionally can be decoded.

Use an approved secure hashing alorithm to verify that something has not been tampered with. Some examples of that are tarballs (both ones you download and also ones you provide to other devs -- always send a hash of the file so the downloader can confirm the file before opening it) and API request bodies.

A fun example is to make a "precommit" statement among friends: create a sentence predicting an outcome, then share the hash of the sentence. When the outcome comes true, share the original text.

Hash-based Message Authentication Code (HMAC)

If using a hash to verify a JSON API body, you and the client might have a shared secret that you concatenate onto the body so you can be sure that it is untampered with.

The way most secure hashing algorithms work is based on blocks of bytes of a specific length. The input is split and padded to fit into the correct length. This leaves them open to a length-extension attack, where a knowledgeable attacker can add on to the input and compute a valid new hash by reverse-engineering the internal state of the hashing function without knowing the secret.

A Hash-based Message Authentication Code (HMAC) is designed to work around that. Instead of hashing the secret concatenated with the message, it hashes the secret concatenated with the hash of the secret concatenated with the message.

It's possible that you will not directly interact with HMACs but they do show up in TLS, JWT, and one-time passwords.

Passwords

Note that for passwords, the attacker does not need to know the user's password per se; the attacker needs to know a string which will generate the desired hash. This is known as a collision attack.

A rainbow table attack is done with a rainbow table: a giant list of every possible string and its resulting hash. Using such a list, the attacker can quickly look up the password given a hash.

A similar attack is to, given one hash, run through every possible string, hashing each one, until you find a match.

Rainbow-table-style attacks have been on the rise since the early 1990s, making typical secure hashing functions inappropriate for passwords.

The first solution is to use a salt: generate a random number, add that to the user's password, and hash that string. Store the salt alongside the hashed password; each user gets their own salt.

Salts destroy rainbow tables and cause headaches for hashing each string one at a time. But not enough of a headache: GPUs are at a point now where they can run secure hashing functions quickly. Too quickly.

The solution is to use a key derivation algorithm. These are much like normal hashing algorithms (they're actually quite different, but that difference is negligible), except they are intentionally slow.

The most common password hashing algorithms are bcrypt, scrypt, and PBKDF2. Each of these require a salt, but handle it themselves: the output of these functions is a string that contains the salt plus the hashed value. Store that entire string as the hashed password.

Encryption

An encryption algorithm is one where a string can be made illegible and then returned back to the original string again, and where decrypting requires an out-of-band secret.

Less abstractly: a string can be encrypted, and then to decrypt you must know the password.

There are two kinds of encryption algorithms: symmetric and asymmetric. A symmetric algorithm is one where the same secret is used to encrypt it and decrypt it. An asymmetric algorithm is one where the string can be encrypted and decrypted using different secrets -- where the person encrypting cannot necessarily decrypt it.

The most popular symmetric algorithms you'll encounter are AES and Twofish. These might be useful for encrypting a file to share with a group of people or for encrypting your filesystem. 1Password uses AES to encrypt an entire vault; it is encrypted at rest, and only decrypted when you enter the passphrase.

Asymmetric encryption algorithms, also known as public/private keypair encryption, are more well-known -- in large part for how tricky they are to get right. Some famous ones are SSH, TLS (previously SSL), and PGP. These start by generating a pair of encryption secrets known as the public and private keys. Anyone with the public key can encrypt a string, but only the holder of the private key can decrypt it.

(The math around asymmetric encryption is cool. I won't go into it.)

Asymmetric keys and messages encrypted using an asymmetric algorithm are larger than messages encrypted using a symmetric algorithm. It is common to use an asymmetric algorithm -- where fewer people need to know the secret of how to decrypt -- to exchange the secrets for a symmetric algorithm, then use a symmetric algorithm for the rest of the exchange. Such a protocol will save bytes and computational power.

In order for any of this to work, you need to get your hands on a confirmed public key. Each public key has a fingerprint -- an abbreviated and easily-confirmable portion of the entire secret. How this works in practice depends on the protocol.

Signing

An asymmetric encryption algorithm can be run in reverse to provide for signing. In this, a private key is used to sign a string, producing a signature string. The public key can be used to verify that the private key was used to generate the signature, proving that the string was in the control of the owner of the private key.

This is useful for certificate authorities, as used by TLS, but also useful for sharing files. You can provide the tarball and the signature, and anyone with your public key can verify that the tarball was created by you (or, at least, anyone with your private key). The Debian package system is built around this.

SSH

SSH defaults to a trust-on-first-use (TOFU) policy: the first time you connect to a server you are asked to confirm the server's public key fingerprint:

The authenticity of host heroku.com can't be established.
RSA key fingerprint is 8tF0wX2WquK45aGKs/Bh1dKmBXH08vxUe0VCJJWOA/o.
Are you sure you want to continue connecting (yes/no)?  

The server admin will need to tell you out of band whether that is the correct fingerprint (Heroku publishes their fingerprint online).

PGP

OpenPGP is a way for users to trust each other; therefore, fingerprint verification happens in person, often in a keysigning party. People will exchange the fingerprint of their PGP key face-to-face, often written on paper, and then later will confirm that the key they have for the person matches the fingerprint on the paper.

This mechanism is called a web of trust.

TLS

Transport Layer Security is a way for a browser to trust a server. The browser ships with a list of trusted public keys. Each Web site serves up its own public key, plus a signature from another key. If the signature is by one of the trusted public keys, the browser accepts the Web site's key; otherwise, it's a failure.

For example, Firefox trusts GlobalSign. thoughtbot.com has a TLS certificate that was signed by GlobalSign. When you visit thoughtbot.com, it sends its public key plus the signature from GlobalSign. Firefox trusts GlobalSign, so it trusts thoughtbot.com's key.

This mechanism is called a certificate authority.

Encrypting and hashing

Encryption (PGP, AES) is different from hashing (SHA-256, bcrypt, etc.), because it can be reversed, and this is different from encoding (base64, base58, etc.) because reversing it requires a password.

It can be handy to combine these technologies:

  • Encrypt and hash. The recipient can confirm that they have the right string by checking the hash before even attempting to decrypt it. This might save them from attempting to decrypt a malicious string.
  • Hash and encode. This can be handy for when you need to triple-check that a JSON payload made it through safely: hash the JSON, then base64 the hash, which encodes it into ASCII, making it safer to send across HTTP.

TLS

Transport Layer Security (TLS) is a general-purpose mechanism for confirming the integrity, confidentiality, and authenticity of data sent over TCP. It combines symmetric encryption, asymmetric encryption, and hashing functions to transmit data securely and efficiently.

It does not guarantee that the domain owner is trustworthy. TLS does not relate to trust. It can only guarantee that the information is sent, untampered and privately, only to the recipient you are sending it to. It does not guarantee that you are sending it to the right recipient.

There are two kinds of certificates signed by certificate authorities: domain verification and extended verification. Domain verification does what it says on the tin: it confirms that the holder of the private key is also in control of the domain name. Extended verification goes further and cannot be automated: it confirms that the holder of the private key controls the domain name and is the person or company they claim to be.

Extended verification does not guarantee that the holder of the private key is trustworthy.

We typically interact with TLS via HTTPS, but it can be used for any TCP connection, such as email.

The first version of TLS was named Secure Sockets Layer (SSL); at the end of the last century, SSL was found to be trivially vulnerable and has not been intentionally used since.

HSTS

The most common attack vector for a secure protocol is a downgrade attack. Many protocols have a backward-compatibility mechanism that allows the client and server to negotiate which version of a protocol they both understand. Convincing the server to downgrade to a version of a protocol with a known bug is a downgrade attack.

The worst case is when you can convince the server to drop the security entirely. This is possible with HTTPS with a standard man-in-the-middle attack of the unencrypted HTTP connection.

It works like this:

  1. User visits twitter.com.
  2. Web browser turns this into http://twitter.com/.
  3. An eavesdropper intercepts the connection and redirects to their own server, secured using TLS, but entirely under their control.

The problem is step (2). The current solution is HTTP Strict Transport Security (HSTS). Under HSTS, the browser knows about domain names that should always be HTTPS. It literally has a list. If you enter twitter.com into the URL bar, it will check its list, find twitter.com in there, and complete the full URL as https://twitter.com/.

Web sites can add themselves to the user's local list by sending the Strict-Transport-Security header. The value for this header is max-age=31536000; includeSubDomains; preload.

  • max-age determines how long this domain should remain in the browser's list. 31536000 is one year. Feel free to go longer.
  • includeSubDomains specifies that subdomains should also be considered part of the HSTS list.
  • preload tells the browser maintainer that you are comfortable with this domain being part of the list shipped with the browser.

Unrelated to HSTS but sort of a corollary of how the attack works: specify the protocol (https://) in all your links.

Passwords

As has been mentioned, use bcrypt for storing your passwords in a database.

Design the user experience to encourage your users to use a password manager:

  • Allow paste. Do the minimum to the password field -- and be sure to annotate that it is a standard password field (type="password" in HTML, android:inputType="password" in Android, passwordTextField.isSecureTextEntry=true in iOS) -- so that the user's password manager can work with it.
  • Never expire passwords. To quote NIST:

    Users tend to choose weaker memorized secrets when they know that they will have to change them in the near future. When those changes do occur, they often select a secret that is similar to their old memorized secret by applying a set of common transformations such as increasing a number in the password. This practice provides a false sense of security if any of the previous secrets has been compromised since attackers can apply these same common transformations.

  • Allow passwords to be more complex. Whether you want to enforce light password complexity rules or not (NIST discourages password complexity rules), allow for passwords longer or otherwise more complex than you expect. When possible, treat passwords as bytes that are immediately hashed and stored.

A good password has a few properties:

  • Complex enough to be hard to crack through a boring enumeration attack.
  • Able to be changed when compromised.
  • Unique to the account.
  • Can be stored securely by the user (in their own head, in a password manager, in a locked notebook, etc.).
  • Can be kept as a secret.
  • Leaking the password only threatens the security of that password.

Biometrics (iris scan, face recognition, thumbprint reader, etc.) violate most of those qualities. Biometrics are useful for identity but incorrect to use as an authentication secret.

Timing attacks

An attacker can learn a lot from how long it takes to be denied access. If it's instant, that means the input didn't even pass validation; if it's kinda long, that means that the input got past validation and computed a hash but one of the first few characters of the hash were incorrect; a longer delay means that most of the hash was right. Knowing how much of the hash was right allows the attacker to narrow the attack space.

The solution: use a constant-time equality check for comparing the hashed values. Bcrypt libraries ship with a function that does everything for you. ActiveSupport ships with secure_compare for constant-time comparisons. Worst case: pad the string to a fixed length then make sure your loop goes through every character even after you know the answer.

Multi-factor authentication (2FA)

Given an email and password, you can authenticate as a user any time you wish. If someone were to mistakenly use the same password for multiple services, it is as strong as the least secure of those services: if the password were leaked, the password for all of those accounts would be leaked along with it.

We can mitigate these kinds of attacks by requiring a second security factor -- for example, a second password. We can go further by defining different categories of authentication:

  • Something you know, such as a string of letters.
  • Something you are, such as biometrics.
  • Something you have, such as a phone.

We can use a HOTP or TOTP algorithm to send and verify short codes out of band to something the user has, such as via email, SMS, an external program, or a hardware key. Email and SMS have known security issues, as we'll discuss later, so lean on an external program or hardware when possible.

OTP

The HMAC-based One-Time Password (HOTP) algorithm, RFC 4226, is a somewhat straightforward function. The details can be found in the RFC but in summary it works like this: the client and server communicate a shared secret (typically via QR code). Whenever you need a one-time password, the shared secret is combined with an incrementing number, hashed, and then six digits are pulled out. Those six digits are the one-time password.

Where can one get an incrementing number that both the client and server know about? We can use the number of minutes since the epoch. This gives us the Time-based One-Time Password (TOTP) algorithm, RFC 6238.

Most languages have a library for handling OTP. Ruby's is called rotp. As always, use the library instead of implementing it yourself.

In practice it goes like this:

  1. Generate a secret. Store this for the user.
  2. Present the secret to the user as a QR code and optionally as a string. The user will use an app to scan the QR code into the OTP app. Some example apps are Google Authenticator and Duo, but the algorithm is simple enough that any app will do.
  3. Prompt the user for an OTP. If they confirm correctly, enable 2FA for them through this method.
  4. Next time they sign in, prompt them for an OTP generated by their app. Confirm it by comparing against the OTP calculated on the server.

Note that the app can run entirely offline: it works by adding a secret key locally and computing an OTP from a combination of hashing functions. However, the counter value (e.g. minutes since epoch) must remain in sync between the server and client. Typically this means using NTP. If debugging, check the time first.

Also note that TOTP is using the minute as the counter. If the client computes the OTP at 12:30:59 and the server computes the OTP at 12:31:02, it will compute a different value. The RFC recommends that the server accept OTP values for any time over the past 30 seconds or the future 30 seconds, to account for latency and drift.

Communicating an OTP

An external app (Google Authenticator, 1Password, or a command-line tool) is the safest easy option for the client: the only point of attack is when the secret is initially communicated, and otherwise using it is offline and out of band.

Sending an OTP from the server is less secure since it provides a window of attack each time the user authenticates. If you can send it securely, such as via an encrypted email or over Signal, that will reduce the attack. Plain text emails and SMS are open to the public and can be read or spoofed by anyone, making them effectively useless for communicating a one-time password.

Sending a one-time password via SMS is more secure than only a single form of authentication.

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