Cryptography in Mobile Apps

Cryptography plays an especially important role in securing the user's data - even more so in a mobile environment, where attackers having physical access to the user's device is a likely scenario. This chapter provides an outline of cryptographic concepts and best practices relevant to mobile apps. These best practices are valid independent of the mobile operating system.

Key Concepts

The goal of cryptography is to provide constant confidentiality, data integrity, and authenticity, even in the face of an attack. Confidentiality involves ensuring data privacy through the use of encryption. Data integrity deals with data consistency and detection of tampering and modification of data. Authenticity ensures that the data comes from a trusted source.

Encryption algorithms converts plaintext data into cipher text that conceals the original content. Plaintext data can be restored from the cipher text through decryption. Encryption can be symmetric (secret-key encryption) or asymmetric (public-key encryption). In general, encryption operations do not protect integrity, but some symmetric encryption modes also feature that protection.

Symmetric-key encryption algorithms use the same key for both encryption and decryption. This type of encryption is fast and suitable for bulk data processing. Since everybody who has access to the key is able to decrypt the encrypted content, this method requires careful key management. Public-key encryption algorithms operate with two separate keys: the public key and the private key. The public key can be distributed freely while the private key shouldn't be shared with anyone. A message encrypted with the public key can only be decrypted with the private key. Since asymmetric encryption is several times slower than symmetric operations, it's typically only used to encrypt small amounts of data, such as symmetric keys for bulk encryption.

Hashing isn't a form of encryption, but it does use cryptography. Hash functions deterministically map arbitrary pieces of data into fixed-length values. It's easy to compute the hash from the input, but very difficult (i.e. infeasible) determine the original input from the hash. Hash functions are used for integrity verification, but don't provide an authenticity guarantee.

Message Authentication Codes (MACs) combine other cryptographic mechanisms (such as symmetric encryption or hashes) with secret keys to provide both integrity and authenticity protection. However, in order to verify a MAC, multiple entities have to share the same secret key and any of those entities can generate a valid MAC. HMACs, the most commonly used type of MAC, rely on hashing as the underlying cryptographic primitive. The full name of an HMAC algorithm usually includes the underlying hash function's type (for example, HMAC-SHA256 uses the SHA-256 hash function).

Signatures combine asymmetric cryptography (that is, using a public/private key pair) with hashing to provide integrity and authenticity by encrypting the hash of the message with the private key. However, unlike MACs, signatures also provide non-repudiation property as the private key should remain unique to the data signer.

Key Derivation Functions (KDFs) derive secret keys from a secret value (such as a password) and are used to turn keys into other formats or to increase their length. KDFs are similar to hashing functions but have other uses as well (for example, they are used as components of multi-party key-agreement protocols). While both hashing functions and KDFs must be difficult to reverse, KDFs have the added requirement that the keys they produce must have a level of randomness.

Identifying Insecure and/or Deprecated Cryptographic Algorithms

When assessing a mobile app, you should make sure that it does not use cryptographic algorithms and protocols that have significant known weaknesses or are otherwise insufficient for modern security requirements. Algorithms that were considered secure in the past may become insecure over time; therefore, it's important to periodically check current best practices and adjust configurations accordingly.

Verify that cryptographic algorithms are up to date and in-line with industry standards. Vulnerable algorithms include outdated block ciphers (such as DES and 3DES), stream ciphers (such as RC4), hash functions (such as MD5 and SHA1), and broken random number generators (such as Dual_EC_DRBG and SHA1PRNG). Note that even algorithms that are certified (for example, by NIST) can become insecure over time. A certification does not replace periodic verification of an algorithm's soundness. Algorithms with known weaknesses should be replaced with more secure alternatives.

Inspect the app's source code to identify instances of cryptographic algorithms that are known to be weak, such as:

The names of cryptographic APIs depend on the particular mobile platform.

Please make sure that:

  • Cryptographic algorithms are up to date and in-line with industry standards. This includes, but is not limited to outdated block ciphers (e.g. DES), stream ciphers (e.g. RC4), as well as hash functions (e.g. MD5) and broken random number generators like Dual_EC_DRBG (even if they are NIST certified). All of these should be marked as insecure and should not be used and removed from the application and server.

  • Key lengths are in-line with industry standards and provide protection for sufficient amount of time. A comparison of different key lengths and protection they provide taking into account Moore's law is available online.

  • Cryptographic means are not mixed with each other: e.g. you do not sign with a public key, or try to reuse a keypair used for a signature to do encryption.

  • Cryptographic parameters are well defined within reasonable range. This includes, but is not limited to: cryptographic salt, which should be at least the same length as hash function output, reasonable choice of password derivation function and iteration count (e.g. PBKDF2, scrypt or bcrypt), IVs being random and unique, fit-for-purpose block encryption modes (e.g. ECB should not be used, except specific cases), key management being done properly (e.g. 3DES should have three independent keys) and so on.

The following algorithms are recommended:

  • Confidentiality algorithms: AES-GCM-256 or ChaCha20-Poly1305

  • Integrity algorithms: SHA-256, SHA-384, SHA-512, Blake2

  • Digital signature algorithms: RSA (3072 bits and higher), ECDSA with NIST P-384

  • Key establishment algorithms: RSA (3072 bits and higher), DH (3072 bits or higher), ECDH with NIST P-384

Additionally, you should always rely on secure hardware (if available) for storing encryption keys, performing cryptographic operations, etc.

For more information on algorithm choice and best practices, see the following resources:

Common Configuration Issues

Insufficient Key Length

Even the most secure encryption algorithm becomes vulnerable to brute-force attacks when that algorithm uses an insufficient key size.

Ensure that the key length fulfills accepted industry standards.

Symmetric Encryption with Hard-Coded Cryptographic Keys

The security of symmetric encryption and keyed hashes (MACs) depends on the secrecy of the key. If the key is disclosed, the security gained by encryption is lost. To prevent this, never store secret keys in the same place as the encrypted data they helped create. Developers often make the mistake of encrypting locally stored data with a static, hard-coded encryption key and compiling that key into the app. This makes the key accessible to anyone who can use a disassembler.

First, ensure that no keys or passwords are stored within the source code. This means you should check native code, JavaScript/Dart code, Java/Kotlin code on Android and Objective-C/Swift in iOS. Note that hard-coded keys are problematic even if the source code is obfuscated since obfuscation is easily bypassed by dynamic instrumentation.

If the app is using two-way SSL (both server and client certificates are validated), make sure that:

  1. The password to the client certificate isn't stored locally or is locked in the device Keychain.

  2. The client certificate isn't shared among all installations.

If the app relies on an additional encrypted container stored in app data, check how the encryption key is used. If a key-wrapping scheme is used, ensure that the master secret is initialized for each user or the container is re-encrypted with new key. If you can use the master secret or previous password to decrypt the container, check how password changes are handled.

Secret keys must be stored in secure device storage whenever symmetric cryptography is used in mobile apps. For more information on the platform-specific APIs, see the Testing Data Storage on Android and Testing Data Storage on iOS chapters.

Weak Key Generation Functions

Cryptographic algorithms (such as symmetric encryption or some MACs) expect a secret input of a given size. For example, AES uses a key of exactly 16 bytes. A native implementation might use the user-supplied password directly as an input key. Using a user-supplied password as an input key has the following problems:

  • If the password is smaller than the key, the full key space isn't used. The remaining space is padded (spaces are sometimes used for padding).

  • A user-supplied password will realistically consist mostly of displayable and pronounceable characters. Therefore, only some of the possible 256 ASCII characters are used and entropy is decreased by approximately a factor of four.

Ensure that passwords aren't directly passed into an encryption function. Instead, the user-supplied password should be passed into a KDF to create a cryptographic key. Choose an appropriate iteration count when using password derivation functions. For example, NIST recommends and iteration count of at least 10,000 for PBKDF2.

Weak Random Number Generators

It is fundamentally impossible to produce truly random numbers on any deterministic device. Pseudo-random number generators (RNG) compensate for this by producing a stream of pseudo-random numbers - a stream of numbers that appear as if they were randomly generated. The quality of the generated numbers varies with the type of algorithm used. Cryptographically secure RNGs generate random numbers that pass statistical randomness tests, and are resilient against prediction attacks.

Mobile SDKs offer standard implementations of RNG algorithms that produce numbers with sufficient artificial randomness. We'll introduce the available APIs in the Android and iOS specific sections.

Custom Implementations of Cryptography

Inventing proprietary cryptographic functions is time consuming, difficult, and likely to fail. Instead, we can use well-known algorithms that are widely regarded as secure. Mobile operating systems offer standard cryptographic APIs that implement those algorithms.

Carefully inspect all the cryptographic methods used within the source code, especially those that are directly applied to sensitive data. All cryptographic operations should use standard cryptographic APIs for Android and iOS (we'll write about those in more detail in the platform-specific chapters). Any cryptographic operations that don't invoke standard routines from known providers should be closely inspected. Pay close attention to standard algorithms that have been modified. Remember that encoding isn't the same as encryption! Always investigate further when you find bit manipulation operators like XOR (exclusive OR).

At all implementations of cryptography, you need to ensure that the following always takes place:

  • Worker keys (like intermediary/derived keys in AES/DES/Rijndael) are properly removed from memory after consumption.

  • The inner state of a cipher should be removed from memory as soon as possible.

Inadequate AES Configuration

Advanced Encryption Standard (AES) is the widely accepted standard for symmetric encryption in mobile apps. It's an iterative block cipher that is based on a series of linked mathematical operations. AES performs a variable number of rounds on the input, each of which involve substitution and permutation of the bytes in the input block. Each round uses a 128-bit round key which is derived from the original AES key.

As of this writing, no efficient cryptanalytic attacks against AES have been discovered. However, implementation details and configurable parameters such as the block cipher mode leave some margin for error.

Weak Block Cipher Mode

Block-based encryption is performed upon discrete input blocks (for example, AES has 128 bit blocks). If the plaintext is larger than the block size, the plaintext is internally split up into blocks of the given input size and encryption is performed on each block. A block cipher mode of operation (or block mode) determines if the result of encrypting the previous block impacts subsequent blocks.

ECB (Electronic Codebook) divides the input into fixed-size blocks that are encrypted separately using the same key. If multiple divided blocks contain the same plaintext, they will be encrypted into identical ciphertext blocks which makes patterns in data easier to identify. It some situations, an attacker might also be able to replay the encrypted data.

Difference of encryption modes

Verify that Cipher Block Chaining (CBC) mode is used instead of ECB. In CBC mode, plaintext blocks are XORed with the previous ciphertext block. This ensures that each encrypted block is unique and randomized even if blocks contain the same information. Please note that it is best to combine CBC with an HMAC and/or ensure that no errors are given such as "Padding error", "MAC error", "decryption failed" in order to be more resistant to a padding oracle attack.

When storing encrypted data, we recommend using a block mode that also protects the integrity of the stored data, such as Galois/Counter Mode (GCM). The latter has the additional benefit that the algorithm is mandatory for each TLSv1.2 implementation, and thus is available on all modern platforms.

For more information on effective block modes, see the NIST guidelines on block mode selection.

Predictable Initialization Vector

CBC, OFB, CFB, PCBC mode require an initialization vector (IV) as an initial input to the cipher. The IV doesn't have to be kept secret, but it shouldn't be predictable. Make sure that IVs are generated using a cryptographically-secure random number generator. For more information on IVs, see Crypto Fail's initialization vectors article.

Initialization Vectors in stateful operation modes

Please note that the usage of IVs is different when using CTR and GCM mode in which the initialization vector is often a counter (in CTR combined with a nonce). So here using a predictable IV with its own stateful model is exactly what is needed. In CTR you have a new nonce plus counter as an input to every new block operation. For example: for a 5120 bit long plaintext: you have 20 blocks, so you need 20 input vectors consisting of a nonce and counter. Whereas in GCM you have a single IV per cryptographic operation, which should not be repeated with the same key. See section 8 of the documentation from NIST on GCM for more details and recommendations of the IV.

Padding Oracle Attacks due to Weaker Padding or Block Operation Implementations

In the old days, PKCS #7 (Public Key Cryptography Standards 7) was used as a padding mechanism when doing asymmetric encryption. Now in modern Java environments it is referred to as PKCS #5. This mechanism is vulnerable to the padding oracle attack. Therefore, it is best to use OEAP (Optimal Asymmetric Encryption Padding) (or PKCS #1 v2.0). Note that, even when using OAEP, you can still run into an issue known best as the Mangers attack as described in the blog at Kudelskisecurity.

Note: AES-CBC with PKCS #5 has shown to be vulnerable to padding oracle attacks as well, given that the implementation gives warnings, such as "Padding error", "MAC error", or "decryption failed". See The Padding Oracle Attack for an example. Next, it is best to ensure that you add an HMAC after you encrypt the plaintext: after all a ciphertext with a failing MAC will not have to be decrypted and can be discarded.

Protecting Keys in Memory

When memory dumping is part of your threat model, then keys can be accessed the moment they are actively used. Memory dumping either requires root-access (e.g. a rooted device or jailbroken device) or it requires a patched application with Frida (so you can use tools like Fridump). Therefore it is best to consider the following, if keys are still needed at the device:

  • make sure that all cryptographic actions and the keys itself remain in the Trusted Execution Environment (e.g. use Android Keystore) or Secure Enclave (e.g. use the Keychain and when you sign, use ECDHE).

  • If keys are necessary which are outside of the TEE / SE, make sure you obfuscate/encrypt them and only de-obfuscate them during use. Always zero out keys before the memory is released, whether using native code or not. This means: overwrite the memory structure (e.g. nullify the array) and know that most of the Immutable types in Android (such as BigInteger and String) stay in the heap.

Note: given the ease of memory dumping, never share the same key among accounts and/or devices, other than public keys used for signature verification or encryption.

Protecting keys in Transport

When keys need to be transported from one device to another, or from the app to a back-end, make sure that proper key protection is in place, by means of an transport keypair or another mechanism. Often, keys are shared with obfuscation methods which can be easily reversed. Instead, make sure asymmetric cryptography or wrapping keys are used.

Cryptographic APIs on Android and iOS

While same basic cryptographic principles apply independent of the particular OS, each operating system offers its own implementation and APIs. Platform-specific cryptographic APIs for data storage are covered in greater detail in the Testing Data Storage on Android and Testing Data Storage on iOS chapters. Encryption of network traffic, especially Transport Layer Security (TLS), is covered in the Testing Network Communication chapter.

Cryptographic policy

In larger organizations, or when high risk applications are created, it can often be a good practice to have a cryptographic policy, based on frameworks such as NIST Recommendation for Key Management. When basic errors are found in the application of cryptography, it can be a good starting point of setting up a lessons learned / cryptographic key management policy.

References

Cryptography References

OWASP Mobile Top 10 2016

OWASP MASVS

  • V1.2: "Security controls are never enforced only on the client side, but on the respective remote endpoints."

  • V1.8: "There is an explicit policy for how cryptographic keys (if any) are managed, and the lifecycle of cryptographic keys is enforced. Ideally, follow a key management standard such as NIST SP 800-57."

  • V3.1: "The app does not rely on symmetric cryptography with hardcoded keys as a sole method of encryption."

  • V3.2: "The app uses proven implementations of cryptographic primitives."

  • V3.3: "The app uses cryptographic primitives that are appropriate for the particular use-case, configured with parameters that adhere to industry best practices."

  • V3.4: "The app does not use cryptographic protocols or algorithms that are widely considered depreciated for security purposes."

  • V7.8: "In unmanaged code, memory is allocated, freed and used securely."

CWE

  • CWE-326 - Inadequate Encryption Strength

  • CWE-327 - Use of a Broken or Risky Cryptographic Algorithm

  • CWE-329 - Not Using a Random IV with CBC Mode