From e16d57a93312b550752c292c8e498c94e3255402 Mon Sep 17 00:00:00 2001
From: Kaan Karaca <kaan94karaca@gmail.com>
Date: Wed, 15 Apr 2026 23:58:13 +0300
Subject: [PATCH] test(crypto): add encryption coverage

---
 .../src/main/crypto/encryption.test.ts        | 268 ++++++++++++++++++
 1 file changed, 268 insertions(+)
 create mode 100644 apps/desktop/src/main/crypto/encryption.test.ts

diff --git a/apps/desktop/src/main/crypto/encryption.test.ts b/apps/desktop/src/main/crypto/encryption.test.ts
new file mode 100644
index 000000000..72841f8be
--- /dev/null
+++ b/apps/desktop/src/main/crypto/encryption.test.ts
@@ -0,0 +1,268 @@
+import { afterEach, beforeAll, describe, expect, it, vi } from 'vitest'
+import sodium from 'libsodium-wrappers-sumo'
+
+import { XCHACHA20_PARAMS } from '@memry/contracts/crypto'
+
+import { CryptoError } from './crypto-errors'
+import {
+  decrypt,
+  decryptMasterKeyFromLinking,
+  encrypt,
+  encryptMasterKeyForLinking,
+  generateNonce,
+  unwrapFileKey,
+  wrapFileKey
+} from './encryption'
+
+beforeAll(async () => {
+  await sodium.ready
+})
+
+afterEach(() => {
+  vi.restoreAllMocks()
+})
+
+const encoder = new TextEncoder()
+const decoder = new TextDecoder()
+
+const makeKey = (): Uint8Array => sodium.randombytes_buf(XCHACHA20_PARAMS.KEY_LENGTH)
+
+const makePayload = (length: number): Uint8Array => {
+  const payload = new Uint8Array(length)
+  for (let i = 0; i < payload.length; i++) {
+    payload[i] = i % 251
+  }
+  return payload
+}
+
+const expectCryptoError = (fn: () => unknown, code: CryptoError['code'], message?: RegExp) => {
+  try {
+    fn()
+    throw new Error('Expected CryptoError to be thrown')
+  } catch (err) {
+    expect(err).toBeInstanceOf(CryptoError)
+    const cryptoError = err as CryptoError
+    expect(cryptoError.code).toBe(code)
+    if (message) {
+      expect(cryptoError.message).toMatch(message)
+    }
+  }
+}
+
+describe('encryption', () => {
+  it('round-trips a payload without associated data', () => {
+    const key = makeKey()
+    const plaintext = encoder.encode('hello, encryption')
+
+    const { ciphertext, nonce } = encrypt(plaintext, key)
+    const recovered = decrypt(ciphertext, nonce, key)
+
+    expect(recovered).toEqual(plaintext)
+  })
+
+  it('round-trips a payload with associated data', () => {
+    const key = makeKey()
+    const plaintext = encoder.encode('hello, aad')
+    const associatedData = encoder.encode('note-metadata')
+
+    const { ciphertext, nonce } = encrypt(plaintext, key, associatedData)
+    const recovered = decrypt(ciphertext, nonce, key, associatedData)
+
+    expect(decoder.decode(recovered)).toBe('hello, aad')
+  })
+
+  it('rejects ciphertext tampering', () => {
+    const key = makeKey()
+    const plaintext = encoder.encode('tamper-me')
+    const { ciphertext, nonce } = encrypt(plaintext, key)
+    const tampered = new Uint8Array(ciphertext)
+    tampered[0] ^= 0xff
+
+    expectCryptoError(
+      () => decrypt(tampered, nonce, key),
+      'DECRYPTION_FAILED',
+      /Ciphertext authentication failed:/
+    )
+  })
+
+  it('rejects a wrong key of the correct length', () => {
+    const key = makeKey()
+    const wrongKey = makeKey()
+    const plaintext = encoder.encode('wrong-key-test')
+    const { ciphertext, nonce } = encrypt(plaintext, key)
+
+    expectCryptoError(
+      () => decrypt(ciphertext, nonce, wrongKey),
+      'DECRYPTION_FAILED',
+      /Ciphertext authentication failed:/
+    )
+  })
+
+  it('rejects a wrong nonce of the correct length', () => {
+    const key = makeKey()
+    const plaintext = encoder.encode('wrong-nonce-test')
+    const { ciphertext, nonce } = encrypt(plaintext, key)
+    const wrongNonce = new Uint8Array(nonce)
+    wrongNonce[0] ^= 0xff
+
+    expectCryptoError(
+      () => decrypt(ciphertext, wrongNonce, key),
+      'DECRYPTION_FAILED',
+      /Ciphertext authentication failed:/
+    )
+  })
+
+  it('rejects associated data mismatches', () => {
+    const key = makeKey()
+    const plaintext = encoder.encode('aad-mismatch')
+    const { ciphertext, nonce } = encrypt(plaintext, key, encoder.encode('aad-a'))
+
+    expectCryptoError(
+      () => decrypt(ciphertext, nonce, key, encoder.encode('aad-b')),
+      'DECRYPTION_FAILED',
+      /Ciphertext authentication failed:/
+    )
+  })
+
+  it('round-trips a zero-length payload', () => {
+    const key = makeKey()
+    const plaintext = new Uint8Array()
+
+    const { ciphertext, nonce } = encrypt(plaintext, key)
+    const recovered = decrypt(ciphertext, nonce, key)
+
+    expect(recovered).toEqual(plaintext)
+    expect(recovered).toHaveLength(0)
+  })
+
+  it('round-trips a payload larger than 1 MiB', () => {
+    const key = makeKey()
+    const plaintext = makePayload(1024 * 1024 + 17)
+    const associatedData = encoder.encode('r2-chunk-boundary')
+
+    const { ciphertext, nonce } = encrypt(plaintext, key, associatedData)
+    const recovered = decrypt(ciphertext, nonce, key, associatedData)
+
+    expect(recovered).toEqual(plaintext)
+    expect(ciphertext.length).toBeGreaterThan(plaintext.length)
+  })
+
+  it('wraps encryption failures as ENCRYPTION_FAILED', () => {
+    const key = makeKey()
+    const plaintext = encoder.encode('boom')
+    const encryptSpy = vi
+      .spyOn(sodium, 'crypto_aead_xchacha20poly1305_ietf_encrypt')
+      .mockImplementation(() => {
+        throw new Error('forced encryption failure')
+      })
+
+    expectCryptoError(
+      () => encrypt(plaintext, key),
+      'ENCRYPTION_FAILED',
+      /forced encryption failure/
+    )
+
+    encryptSpy.mockRestore()
+  })
+
+  it('wraps non-error encryption failures as ENCRYPTION_FAILED', () => {
+    const key = makeKey()
+    const plaintext = encoder.encode('boom-string')
+    const encryptSpy = vi
+      .spyOn(sodium, 'crypto_aead_xchacha20poly1305_ietf_encrypt')
+      .mockImplementation(() => {
+        throw 'forced string failure'
+      })
+
+    expectCryptoError(() => encrypt(plaintext, key), 'ENCRYPTION_FAILED', /Encryption failed/)
+
+    encryptSpy.mockRestore()
+  })
+
+  it('wraps non-authentication decrypt failures without a ciphertext prefix', () => {
+    const key = makeKey()
+    const plaintext = encoder.encode('decrypt-failure')
+    const { ciphertext, nonce } = encrypt(plaintext, key)
+    const decryptSpy = vi
+      .spyOn(sodium, 'crypto_aead_xchacha20poly1305_ietf_decrypt')
+      .mockImplementation(() => {
+        throw new Error('forced decrypt failure')
+      })
+
+    expectCryptoError(() => decrypt(ciphertext, nonce, key), 'DECRYPTION_FAILED', /forced decrypt failure/)
+
+    decryptSpy.mockRestore()
+  })
+
+  it('wraps non-Error decrypt failures as a generic decryption error', () => {
+    const key = makeKey()
+    const plaintext = encoder.encode('decrypt-non-error')
+    const { ciphertext, nonce } = encrypt(plaintext, key)
+    const decryptSpy = vi
+      .spyOn(sodium, 'crypto_aead_xchacha20poly1305_ietf_decrypt')
+      .mockImplementation(() => {
+        throw 'forced string failure'
+      })
+
+    expectCryptoError(() => decrypt(ciphertext, nonce, key), 'DECRYPTION_FAILED', /Decryption failed/)
+
+    decryptSpy.mockRestore()
+  })
+
+  it('throws when sodium returns a nonce with the wrong length', () => {
+    const randombytesSpy = vi.spyOn(sodium, 'randombytes_buf').mockReturnValueOnce(
+      new Uint8Array(XCHACHA20_PARAMS.NONCE_LENGTH - 1)
+    )
+
+    expect(() => generateNonce()).toThrow(
+      `Nonce length mismatch: expected ${XCHACHA20_PARAMS.NONCE_LENGTH}, got ${XCHACHA20_PARAMS.NONCE_LENGTH - 1}`
+    )
+
+    randombytesSpy.mockRestore()
+  })
+
+  it('round-trips the master-key linking helpers', () => {
+    const encKey = makeKey()
+    const masterKey = makePayload(32)
+
+    const { ciphertext, nonce } = encryptMasterKeyForLinking(masterKey, encKey)
+    const recovered = decryptMasterKeyFromLinking(ciphertext, nonce, encKey)
+
+    expect(recovered).toEqual(masterKey)
+  })
+
+  it('wraps and unwraps file keys while zeroing the intermediate buffer', () => {
+    const vaultKey = makeKey()
+    const fileKey = makePayload(32)
+    const { wrappedKey, nonce } = wrapFileKey(fileKey, vaultKey)
+    const memzeroSpy = vi.spyOn(sodium, 'memzero')
+
+    const recovered = unwrapFileKey(wrappedKey, nonce, vaultKey)
+
+    expect(recovered).toEqual(fileKey)
+    expect(memzeroSpy).toHaveBeenCalledTimes(1)
+    expect(memzeroSpy.mock.calls[0][0]).toBeInstanceOf(Uint8Array)
+    expect(memzeroSpy.mock.calls[0][0]).toHaveLength(32)
+  })
+
+  it('rejects invalid key and nonce lengths', () => {
+    const plaintext = encoder.encode('length-check')
+    const validKey = makeKey()
+    const shortKey = new Uint8Array(XCHACHA20_PARAMS.KEY_LENGTH - 1)
+    const { ciphertext, nonce } = encrypt(plaintext, validKey)
+    const shortNonce = new Uint8Array(XCHACHA20_PARAMS.NONCE_LENGTH - 1)
+
+    expectCryptoError(
+      () => encrypt(plaintext, shortKey),
+      'INVALID_KEY_LENGTH'
+    )
+    expectCryptoError(
+      () => decrypt(ciphertext, nonce, shortKey),
+      'INVALID_KEY_LENGTH'
+    )
+    expectCryptoError(
+      () => decrypt(ciphertext, shortNonce, validKey),
+      'INVALID_NONCE_LENGTH'
+    )
+  })
+})