ssh_keys.c File Reference

Go to the source code of this file.

Functions
asciichat_error_t	parse_ssh_ed25519_line (const char *line, uint8_t ed25519_pk[32])
asciichat_error_t	parse_ssh_private_key (const char *key_path, private_key_t *key_out)
asciichat_error_t	validate_ssh_key_file (const char *key_path)
asciichat_error_t	ed25519_to_x25519_public (const uint8_t ed25519_pk[32], uint8_t x25519_pk[32])
asciichat_error_t	ed25519_to_x25519_private (const uint8_t ed25519_sk[64], uint8_t x25519_sk[32])
asciichat_error_t	ed25519_sign_message (const private_key_t *key, const uint8_t *message, size_t message_len, uint8_t signature[64])
asciichat_error_t	ed25519_verify_signature (const uint8_t public_key[32], const uint8_t *message, size_t message_len, const uint8_t signature[64], const char *gpg_key_id)

Function Documentation

ed25519_sign_message()

asciichat_error_t ed25519_sign_message	(	const private_key_t *	key,
		const uint8_t *	message,
		size_t	message_len,
		uint8_t	signature[64]
	)

Definition at line 1031 of file ssh_keys.c.

                                                              {
  if (!key || !message || !signature) {
    return SET_ERRNO(ERROR_INVALID_PARAM, "Invalid parameters: key=%p, message=%p, signature=%p", key, message,
                     signature);
  }
 
  if (key->type != KEY_TYPE_ED25519) {
    return SET_ERRNO(ERROR_CRYPTO_KEY, "Key is not an Ed25519 key");
  }
 
  // If using GPG agent, delegate signing to GPG agent
  if (key->use_gpg_agent) {
    log_debug("Using GPG agent for Ed25519 signing (keygrip: %.40s)", key->gpg_keygrip);
 
    // Connect to GPG agent
    int agent_sock = gpg_agent_connect();
    log_debug("GPG agent connection result: %d", agent_sock);
 
    if (agent_sock < 0) {
      log_debug("GPG agent not available, falling back to gpg --detach-sign for signing");
 
      // Extract GPG key ID from key comment ("GPG key <key_id>")
      const char *key_id_prefix = "GPG key ";
      const char *key_id = NULL;
      if (strncmp(key->key_comment, key_id_prefix, strlen(key_id_prefix)) == 0) {
        key_id = key->key_comment + strlen(key_id_prefix);
      }
 
      log_debug("Extracted GPG key ID: %s (len=%zu)", key_id ? key_id : "NULL", key_id ? strlen(key_id) : 0);
 
      if (!key_id || strlen(key_id) != 16) {
        return SET_ERRNO(ERROR_CRYPTO, "Cannot extract GPG key ID from comment for fallback signing");
      }
 
      // Use gpg --detach-sign fallback
      log_debug("Calling gpg_sign_detached_ed25519 with key %s", key_id);
      int result = gpg_sign_detached_ed25519(key_id, message, message_len, signature);
      log_debug("gpg_sign_detached_ed25519 result: %d", result);
 
      if (result != 0) {
        return SET_ERRNO(ERROR_CRYPTO, "GPG fallback signing failed (both agent and gpg command failed)");
      }
 
      log_debug("Successfully signed message with gpg --detach-sign fallback (64 bytes)");
      return ASCIICHAT_OK;
    }
 
    log_debug("Using GPG agent for signing");
 
    // Sign the message using GPG agent
    size_t sig_len = 0;
    int result = gpg_agent_sign(agent_sock, key->gpg_keygrip, message, message_len, signature, &sig_len);
 
    // Disconnect from agent
    gpg_agent_disconnect(agent_sock);
 
    if (result != 0) {
      return SET_ERRNO(ERROR_CRYPTO, "GPG agent signing failed");
    }
 
    if (sig_len != 64) {
      return SET_ERRNO(ERROR_CRYPTO, "GPG agent returned invalid signature length: %zu (expected 64)", sig_len);
    }
 
    log_debug("Successfully signed message with GPG agent (64 bytes)");
    return ASCIICHAT_OK;
  }
 
  // If using SSH agent, delegate signing to SSH agent
  if (key->use_ssh_agent) {
    log_debug("Using SSH agent for Ed25519 signing");
 
    // Create a public_key_t from the stored public key
    public_key_t pub_key = {0};
    pub_key.type = KEY_TYPE_ED25519;
    memcpy(pub_key.key, key->public_key, 32);
 
    // Sign using SSH agent
    asciichat_error_t result = ssh_agent_sign(&pub_key, message, message_len, signature);
    if (result != ASCIICHAT_OK) {
      return result; // Error already set by ssh_agent_sign
    }
 
    log_debug("Successfully signed message with SSH agent (64 bytes)");
    return ASCIICHAT_OK;
  }
 
  // Sign the message with Ed25519 (in-memory key)
  if (crypto_sign_detached(signature, NULL, message, message_len, key->key.ed25519) != 0) {
    return SET_ERRNO(ERROR_CRYPTO, "Failed to sign message with Ed25519");
  }
 
  return ASCIICHAT_OK;
}

References gpg_agent_connect(), gpg_agent_disconnect(), gpg_agent_sign(), gpg_sign_detached_ed25519(), and ssh_agent_sign().

Referenced by crypto_handshake_client_key_exchange(), and crypto_handshake_server_start().

ed25519_to_x25519_private()

asciichat_error_t ed25519_to_x25519_private	(	const uint8_t	ed25519_sk[64],
		uint8_t	x25519_sk[32]
	)

Definition at line 1014 of file ssh_keys.c.

                                                                                                 {
  if (!ed25519_sk || !x25519_sk) {
    return SET_ERRNO(ERROR_INVALID_PARAM, "Invalid parameters: ed25519_sk=%p, x25519_sk=%p", ed25519_sk, x25519_sk);
  }
 
  // Convert Ed25519 private key to X25519 private key
  if (crypto_sign_ed25519_sk_to_curve25519(x25519_sk, ed25519_sk) != 0) {
    return SET_ERRNO(ERROR_CRYPTO_KEY, "Failed to convert Ed25519 private key to X25519");
  }
 
  return ASCIICHAT_OK;
}

Referenced by private_key_to_x25519().

ed25519_to_x25519_public()

asciichat_error_t ed25519_to_x25519_public	(	const uint8_t	ed25519_pk[32],
		uint8_t	x25519_pk[32]
	)

Definition at line 1001 of file ssh_keys.c.

                                                                                                {
  if (!ed25519_pk || !x25519_pk) {
    return SET_ERRNO(ERROR_INVALID_PARAM, "Invalid parameters: ed25519_pk=%p, x25519_pk=%p", ed25519_pk, x25519_pk);
  }
 
  // Convert Ed25519 public key to X25519 public key
  if (crypto_sign_ed25519_pk_to_curve25519(x25519_pk, ed25519_pk) != 0) {
    return SET_ERRNO(ERROR_CRYPTO_KEY, "Failed to convert Ed25519 public key to X25519");
  }
 
  return ASCIICHAT_OK;
}

Referenced by public_key_to_x25519().

ed25519_verify_signature()

asciichat_error_t ed25519_verify_signature	(	const uint8_t	public_key[32],
		const uint8_t *	message,
		size_t	message_len,
		const uint8_t	signature[64],
		const char *	gpg_key_id
	)

Definition at line 1127 of file ssh_keys.c.

                                                                                                {
  if (!public_key || !message || !signature) {
    return SET_ERRNO(ERROR_INVALID_PARAM, "Invalid parameters: public_key=%p, message=%p, signature=%p", public_key,
                     message, signature);
  }
 
  // Try standard Ed25519 verification first
  if (crypto_sign_verify_detached(signature, message, message_len, public_key) == 0) {
    return ASCIICHAT_OK;
  }
 
  // If standard verification fails, try GPG fallback (for GPG-signed messages)
  // Use provided gpg_key_id if available, otherwise check environment variable (for tests)
  const char *key_id_to_use = gpg_key_id;
  size_t key_id_len = key_id_to_use ? strlen(key_id_to_use) : 0;
  // Accept 8, 16, or 40 character GPG key IDs (short, long, or full fingerprint)
  bool valid_key_id = (key_id_len == 8 || key_id_len == 16 || key_id_len == 40);
 
  if (!valid_key_id) {
    key_id_to_use = platform_getenv("TEST_GPG_KEY_ID");
    key_id_len = key_id_to_use ? strlen(key_id_to_use) : 0;
    valid_key_id = (key_id_len == 8 || key_id_len == 16 || key_id_len == 40);
  }
 
  if (valid_key_id) {
    log_debug("Standard Ed25519 verification failed, trying GPG fallback with key %s", key_id_to_use);
    int gpg_result = gpg_verify_detached_ed25519(key_id_to_use, message, message_len, signature);
    if (gpg_result == 0) {
      log_debug("GPG verification succeeded");
      return ASCIICHAT_OK;
    }
    log_debug("GPG verification also failed");
  }
 
  return SET_ERRNO(ERROR_CRYPTO, "Ed25519 signature verification failed (tried both libsodium and GPG)");
}

References gpg_verify_detached_ed25519(), and platform_getenv().

Referenced by crypto_handshake_client_key_exchange(), crypto_handshake_server_auth_challenge(), and crypto_handshake_server_complete().

parse_ssh_ed25519_line()

asciichat_error_t parse_ssh_ed25519_line	(	const char *	line,
		uint8_t	ed25519_pk[32]
	)

Definition at line 164 of file ssh_keys.c.

                                                                                   {
  if (!line || !ed25519_pk) {
    return SET_ERRNO(ERROR_INVALID_PARAM, "Invalid parameters: line=%p, ed25519_pk=%p", line, ed25519_pk);
  }
 
  // Use regex to parse and extract SSH public key components
  char *base64_key = NULL, *comment = NULL;
  if (!crypto_regex_match_public_key(line, &base64_key, &comment)) {
    return SET_ERRNO(ERROR_CRYPTO_KEY, "SSH key line does not match expected format");
  }
 
  // Base64 decode
  uint8_t *blob;
  size_t blob_len;
  if (base64_decode_ssh_key(base64_key, strlen(base64_key), &blob, &blob_len) != 0) {
    SAFE_FREE(base64_key);
    SAFE_FREE(comment);
    return SET_ERRNO(ERROR_CRYPTO_KEY, "Failed to decode SSH key base64 data");
  }
 
  // Clean up regex-extracted strings
  SAFE_FREE(base64_key);
  SAFE_FREE(comment);
 
  // Parse SSH key blob structure:
  // [4 bytes: length of "ssh-ed25519"]
  // [11 bytes: "ssh-ed25519"]
  // [4 bytes: length of public key (32)]
  // [32 bytes: Ed25519 public key]
 
  if (blob_len < SSH_KEY_HEADER_SIZE) {
    SAFE_FREE(blob);
    return SET_ERRNO(ERROR_CRYPTO_KEY, "SSH key blob too small: %zu bytes (expected at least %d)", blob_len,
                     SSH_KEY_HEADER_SIZE);
  }
 
  // Extract Ed25519 public key (last 32 bytes)
  memcpy(ed25519_pk, blob + blob_len - ED25519_PUBLIC_KEY_SIZE, ED25519_PUBLIC_KEY_SIZE);
  SAFE_FREE(blob);
 
  return ASCIICHAT_OK;
}

References crypto_regex_match_public_key().

Referenced by parse_public_key(), and parse_ssh_private_key().

parse_ssh_private_key()

asciichat_error_t parse_ssh_private_key	(	const char *	key_path,
		private_key_t *	key_out
	)

Definition at line 207 of file ssh_keys.c.

                                                                                      {
  if (!key_path || !key_out) {
    return SET_ERRNO(ERROR_INVALID_PARAM, "Invalid parameters: key_path=%p, key_out=%p", key_path, key_out);
  }
 
  // First, check if we can get the key from ssh-agent (password-free)
  // This requires reading the public key from the .pub file
  char pub_key_path[BUFFER_SIZE_LARGE];
  safe_snprintf(pub_key_path, sizeof(pub_key_path), "%s.pub", key_path);
 
  FILE *pub_f = platform_fopen(pub_key_path, "r");
  if (pub_f) {
    char pub_line[BUFFER_SIZE_LARGE];
    if (fgets(pub_line, sizeof(pub_line), pub_f)) {
      public_key_t pub_key = {0};
      pub_key.type = KEY_TYPE_ED25519;
 
      if (parse_ssh_ed25519_line(pub_line, pub_key.key) == ASCIICHAT_OK) {
        // Check if this key is in ssh-agent
        if (ssh_agent_has_key(&pub_key)) {
          fclose(pub_f);
          log_dev("Key found in ssh-agent - using cached key (no password required)");
          // Key is in agent, we can use it
          key_out->type = KEY_TYPE_ED25519;
          key_out->use_ssh_agent = true;
          memcpy(key_out->key.ed25519 + 32, pub_key.key, 32); // Copy public key to second half
          memcpy(key_out->public_key, pub_key.key, 32);       // Also store in public_key field
          // Note: We don't have the private key seed, but ssh-agent will sign for us
          return ASCIICHAT_OK;
        } else {
          log_debug("Key not found in ssh-agent - will decrypt from file");
        }
      }
    }
    fclose(pub_f);
  }
 
  // Validate the SSH key file first
  asciichat_error_t validation_result = validate_ssh_key_file(key_path);
  if (validation_result != ASCIICHAT_OK) {
    return validation_result;
  }
 
  // Read the private key file
  FILE *f = platform_fopen(key_path, "r");
  if (!f) {
    return SET_ERRNO(ERROR_CRYPTO_KEY, "Cannot read private key file: %s", key_path);
  }
 
  // Read the entire file
  char *file_content = NULL;
  size_t file_size = 0;
  char buffer[BUFFER_SIZE_XXLARGE];
  size_t bytes_read;
 
  while ((bytes_read = fread(buffer, 1, sizeof(buffer), f)) > 0) {
    file_content = SAFE_REALLOC(file_content, file_size + bytes_read + 1, char *);
    if (!file_content) {
      (void)fclose(f);
      return SET_ERRNO(ERROR_CRYPTO_KEY, "Out of memory reading private key file");
    }
    memcpy(file_content + file_size, buffer, bytes_read);
    file_size += bytes_read;
  }
  (void)fclose(f);
 
  if (file_size == 0) {
    SAFE_FREE(file_content);
    return SET_ERRNO(ERROR_CRYPTO_KEY, "Private key file is empty: %s", key_path);
  }
 
  file_content[file_size] = '\0';
 
  // Use regex to extract base64 data from OpenSSH PEM format
  char *pem_base64_data = NULL;
  if (!crypto_regex_extract_pem_base64(file_content, &pem_base64_data)) {
    SAFE_FREE(file_content);
    return SET_ERRNO(ERROR_CRYPTO_KEY, "Invalid OpenSSH private key format: %s", key_path);
  }
 
  // Remove any whitespace/newlines from the base64 data
  char *clean_base64 = SAFE_MALLOC(strlen(pem_base64_data) + 1, char *);
  char *clean_ptr = clean_base64;
  for (const char *p = pem_base64_data; *p; p++) {
    if (*p != '\n' && *p != '\r' && *p != ' ' && *p != '\t') {
      *clean_ptr++ = *p;
    }
  }
  *clean_ptr = '\0';
  SAFE_FREE(pem_base64_data);
 
  // Decode the base64 data
  uint8_t *key_blob;
  size_t key_blob_len;
  asciichat_error_t decode_result = base64_decode_ssh_key(clean_base64, strlen(clean_base64), &key_blob, &key_blob_len);
  SAFE_FREE(clean_base64);
 
  if (decode_result != ASCIICHAT_OK) {
    SAFE_FREE(file_content);
    return decode_result;
  }
 
  // Parse the OpenSSH private key structure
  // Format: [4 bytes: magic] [4 bytes: ciphername length] [ciphername] [4 bytes: kdfname length] [kdfname]
  //         [4 bytes: kdfoptions length] [kdfoptions] [4 bytes: num keys] [4 bytes: pubkey length] [pubkey]
  //         [4 bytes: privkey length] [privkey]
 
  if (key_blob_len < 4) {
    SAFE_FREE(key_blob);
    SAFE_FREE(file_content);
    return SET_ERRNO(ERROR_CRYPTO_KEY, "OpenSSH private key blob too small: %s", key_path);
  }
 
  // Check magic number (should be "openssh-key-v1\0")
  if (memcmp(key_blob, "openssh-key-v1\0", 15) != 0) {
    SAFE_FREE(key_blob);
    SAFE_FREE(file_content);
    return SET_ERRNO(ERROR_CRYPTO_KEY, "Invalid OpenSSH private key magic: %s", key_path);
  }
 
  size_t offset = 15; // Skip magic
 
  // Read ciphername
  if (offset + 4 > key_blob_len) {
    SAFE_FREE(key_blob);
    SAFE_FREE(file_content);
    return SET_ERRNO(ERROR_CRYPTO_KEY, "OpenSSH private key truncated at ciphername: %s", key_path);
  }
 
  uint32_t ciphername_len = read_u32_be(&key_blob[offset]);
  offset += 4;
 
  if (offset + ciphername_len > key_blob_len) {
    SAFE_FREE(key_blob);
    SAFE_FREE(file_content);
    return SET_ERRNO(ERROR_CRYPTO_KEY, "OpenSSH private key truncated at ciphername data: %s", key_path);
  }
 
  // Store the position of ciphername for later use
  size_t ciphername_pos = offset;
 
  // Check if key is encrypted
  bool is_encrypted = (ciphername_len > 0 && memcmp(key_blob + offset, "none", 4) != 0);
 
  offset += ciphername_len;
 
  // Skip kdfname and kdfoptions (we don't support encryption)
  if (offset + 4 > key_blob_len) {
    SAFE_FREE(key_blob);
    SAFE_FREE(file_content);
    return SET_ERRNO(ERROR_CRYPTO_KEY, "OpenSSH private key truncated at kdfname: %s", key_path);
  }
 
  uint32_t kdfname_len = read_u32_be(&key_blob[offset]);
  offset += 4;
 
  // Store the position of kdfname for later use
  size_t kdfname_pos = offset;
 
  offset += kdfname_len;
 
  if (offset + 4 > key_blob_len) {
    SAFE_FREE(key_blob);
    SAFE_FREE(file_content);
    return SET_ERRNO(ERROR_CRYPTO_KEY, "OpenSSH private key truncated at kdfoptions: %s", key_path);
  }
 
  uint32_t kdfoptions_len = read_u32_be(&key_blob[offset]);
  offset += 4 + kdfoptions_len;
 
  // Handle encrypted keys
  if (is_encrypted) {
    // Parse the cipher name from the stored position
    char ciphername[32] = {0};
    if (ciphername_len > 0 && ciphername_len < sizeof(ciphername)) {
      memcpy(ciphername, key_blob + ciphername_pos, ciphername_len);
    }
 
    // Parse the KDF name from the stored position
    char kdfname[32] = {0};
    if (kdfname_len > 0 && kdfname_len < sizeof(kdfname)) {
      memcpy(kdfname, key_blob + kdfname_pos, kdfname_len);
    }
 
    log_debug("Cipher: %s, KDF: %s", ciphername, kdfname);
 
    // Check if we support this encryption method
    if (strcmp(ciphername, "aes256-ctr") != 0 && strcmp(ciphername, "aes256-cbc") != 0) {
      SAFE_FREE(key_blob);
      SAFE_FREE(file_content);
      return SET_ERRNO(ERROR_CRYPTO_KEY,
                       "Unsupported cipher '%s' for encrypted SSH key: %s\n"
                       "Supported ciphers: aes256-ctr, aes256-cbc",
                       ciphername, key_path);
    }
 
    if (strcmp(kdfname, "bcrypt") != 0) {
      SAFE_FREE(key_blob);
      SAFE_FREE(file_content);
      return SET_ERRNO(ERROR_CRYPTO_KEY,
                       "Unsupported KDF '%s' for encrypted SSH key: %s\n"
                       "Only bcrypt KDF is supported",
                       kdfname, key_path);
    }
 
    // Parse KDF options (bcrypt salt and rounds)
    if (kdfoptions_len < 8) {
      SAFE_FREE(key_blob);
      SAFE_FREE(file_content);
      return SET_ERRNO(ERROR_CRYPTO_KEY, "Invalid KDF options length: %s", key_path);
    }
 
    // Parse KDF options: [salt_length:4][salt:N][rounds:4]
    size_t kdf_opt_offset = offset - kdfoptions_len;
 
    // Read salt length
    if (kdf_opt_offset + 4 > key_blob_len) {
      SAFE_FREE(key_blob);
      SAFE_FREE(file_content);
      return SET_ERRNO(ERROR_CRYPTO_KEY, "KDF options truncated at salt length: %s", key_path);
    }
    uint32_t salt_len = read_u32_be(&key_blob[kdf_opt_offset]);
    kdf_opt_offset += 4;
 
    // Read salt
    if (salt_len != 16) {
      SAFE_FREE(key_blob);
      SAFE_FREE(file_content);
      return SET_ERRNO(ERROR_CRYPTO_KEY, "Unexpected bcrypt salt length %u (expected 16): %s", salt_len, key_path);
    }
    if (kdf_opt_offset + salt_len > key_blob_len) {
      SAFE_FREE(key_blob);
      SAFE_FREE(file_content);
      return SET_ERRNO(ERROR_CRYPTO_KEY, "KDF options truncated at salt data: %s", key_path);
    }
    uint8_t bcrypt_salt[16];
    memcpy(bcrypt_salt, key_blob + kdf_opt_offset, salt_len);
    kdf_opt_offset += salt_len;
 
    // Read rounds
    if (kdf_opt_offset + 4 > key_blob_len) {
      SAFE_FREE(key_blob);
      SAFE_FREE(file_content);
      return SET_ERRNO(ERROR_CRYPTO_KEY, "KDF options truncated at rounds: %s", key_path);
    }
    uint32_t bcrypt_rounds = read_u32_be(&key_blob[kdf_opt_offset]);
 
    // Check for password in environment variable first
    const char *env_password = platform_getenv("ASCII_CHAT_KEY_PASSWORD");
    char *password = NULL;
    if (env_password && strlen(env_password) > 0) {
      // Use password from environment variable
      password = platform_strdup(env_password);
      if (!password) {
        SAFE_FREE(key_blob);
        SAFE_FREE(file_content);
        return SET_ERRNO(ERROR_MEMORY, "Failed to allocate memory for password");
      }
    } else {
      // Prompt for password interactively - allocate buffer for input
      password = SAFE_MALLOC(1024, char *);
      if (!password) {
        SAFE_FREE(key_blob);
        SAFE_FREE(file_content);
        return SET_ERRNO(ERROR_MEMORY, "Failed to allocate memory for password");
      }
      if (prompt_password_simple("Encrypted SSH key - enter passphrase", password, 1024) != 0) {
        SAFE_FREE(key_blob);
        SAFE_FREE(file_content);
        return SET_ERRNO(ERROR_CRYPTO_KEY, "Failed to read passphrase for encrypted key: %s", key_path);
      }
    }
 
    // Native OpenSSH key decryption using bcrypt_pbkdf + BearSSL AES
 
    // Skip past the unencrypted public key section to get to encrypted private keys
    // Format: [num_keys:4][pubkey_len:4][pubkey:N]...[encrypted_len:4][encrypted:N]
 
    // Read num_keys
    if (offset + 4 > key_blob_len) {
      sodium_memzero(password, strlen(password));
      SAFE_FREE(password);
      SAFE_FREE(key_blob);
      SAFE_FREE(file_content);
      return SET_ERRNO(ERROR_CRYPTO_KEY, "Encrypted key truncated at num_keys: %s", key_path);
    }
    uint32_t num_keys = read_u32_be(&key_blob[offset]);
    offset += 4;
    log_debug("num_keys=%u", num_keys);
 
    // Skip all public keys
    for (uint32_t i = 0; i < num_keys; i++) {
      if (offset + 4 > key_blob_len) {
        sodium_memzero(password, strlen(password));
        SAFE_FREE(password);
        SAFE_FREE(key_blob);
        SAFE_FREE(file_content);
        return SET_ERRNO(ERROR_CRYPTO_KEY, "Encrypted key truncated at pubkey %u length: %s", i, key_path);
      }
      uint32_t pubkey_len = read_u32_be(&key_blob[offset]);
      offset += 4;
      log_debug("Skipping public key %u: %u bytes", i, pubkey_len);
 
      if (offset + pubkey_len > key_blob_len) {
        sodium_memzero(password, strlen(password));
        SAFE_FREE(password);
        SAFE_FREE(key_blob);
        SAFE_FREE(file_content);
        return SET_ERRNO(ERROR_CRYPTO_KEY, "Encrypted key truncated at pubkey %u data: %s", i, key_path);
      }
      offset += pubkey_len;
    }
 
    // Read encrypted private keys length
    if (offset + 4 > key_blob_len) {
      sodium_memzero(password, strlen(password));
      SAFE_FREE(password);
      SAFE_FREE(key_blob);
      SAFE_FREE(file_content);
      return SET_ERRNO(ERROR_CRYPTO_KEY, "Encrypted key truncated at encrypted_len: %s", key_path);
    }
    uint32_t encrypted_len = read_u32_be(&key_blob[offset]);
    offset += 4;
 
    // Now offset points to the actual encrypted data
    size_t encrypted_data_start = offset;
    size_t encrypted_data_len = encrypted_len;
 
    if (encrypted_data_len < 16) {
      sodium_memzero(password, strlen(password));
      SAFE_FREE(password);
      SAFE_FREE(key_blob);
      SAFE_FREE(file_content);
      return SET_ERRNO(ERROR_CRYPTO_KEY, "Encrypted data too small: %s", key_path);
    }
 
    // Extract encrypted blob (includes everything from offset onwards)
    const uint8_t *encrypted_blob = key_blob + encrypted_data_start;
 
    // Call native decryption function
    uint8_t *decrypted_blob = NULL;
    size_t decrypted_blob_len = 0;
 
    // Note: decrypt_openssh_private_key derives IV from bcrypt_pbkdf, not from encrypted data
    asciichat_error_t decrypt_result =
        decrypt_openssh_private_key(encrypted_blob, encrypted_data_len, password, bcrypt_salt, salt_len, bcrypt_rounds,
                                    ciphername, &decrypted_blob, &decrypted_blob_len);
 
    // Clean up password immediately after use
    sodium_memzero(password, strlen(password));
    SAFE_FREE(password);
 
    if (decrypt_result != ASCIICHAT_OK) {
      SAFE_FREE(key_blob);
      SAFE_FREE(file_content);
      return decrypt_result;
    }
 
    // Parse the decrypted private key structure
    // OpenSSH format (decrypted):
    //   [checkint1:4][checkint2:4][keytype:string][pubkey:string][privkey:string][comment:string][padding:N]
 
    if (decrypted_blob_len < 8) {
      SAFE_FREE(decrypted_blob);
      SAFE_FREE(key_blob);
      SAFE_FREE(file_content);
      return SET_ERRNO(ERROR_CRYPTO_KEY, "Decrypted data too small (no checkints): %s", key_path);
    }
 
    // Verify checkints (first 8 bytes should be two identical 32-bit values)
    uint32_t checkint1 = read_u32_be(&decrypted_blob[0]);
    uint32_t checkint2 = read_u32_be(&decrypted_blob[4]);
    if (checkint1 != checkint2) {
      SAFE_FREE(decrypted_blob);
      SAFE_FREE(key_blob);
      SAFE_FREE(file_content);
      return SET_ERRNO(ERROR_CRYPTO_KEY,
                       "Incorrect passphrase or corrupted key (checkint mismatch): %s\n"
                       "Expected matching checkints, got 0x%08x != 0x%08x",
                       key_path, checkint1, checkint2);
    }
 
    // Parse the decrypted private key structure manually
    // Format after checkints: [keytype:string][pubkey:string][privkey:string][comment:string][padding:N]
    size_t dec_offset = 8; // Skip checkints
 
    // Read keytype length
    if (dec_offset + 4 > decrypted_blob_len) {
      SAFE_FREE(decrypted_blob);
      SAFE_FREE(key_blob);
      SAFE_FREE(file_content);
      return SET_ERRNO(ERROR_CRYPTO_KEY, "Decrypted key truncated at keytype length: %s", key_path);
    }
    uint32_t keytype_len = read_u32_be(&decrypted_blob[dec_offset]);
    dec_offset += 4;
 
    // Read keytype
    if (dec_offset + keytype_len > decrypted_blob_len) {
      SAFE_FREE(decrypted_blob);
      SAFE_FREE(key_blob);
      SAFE_FREE(file_content);
      return SET_ERRNO(ERROR_CRYPTO_KEY, "Decrypted key truncated at keytype data: %s", key_path);
    }
    char keytype[BUFFER_SIZE_SMALL / 4] = {0}; // SSH key type strings are short
    if (keytype_len > 0 && keytype_len < sizeof(keytype)) {
      memcpy(keytype, decrypted_blob + dec_offset, keytype_len);
    }
    dec_offset += keytype_len;
 
    // Check if it's Ed25519
    if (strcmp(keytype, "ssh-ed25519") != 0) {
      SAFE_FREE(decrypted_blob);
      SAFE_FREE(key_blob);
      SAFE_FREE(file_content);
      return SET_ERRNO(ERROR_CRYPTO_KEY, "Unsupported key type after decryption: '%s'", keytype);
    }
 
    // Read public key length
    if (dec_offset + 4 > decrypted_blob_len) {
      SAFE_FREE(decrypted_blob);
      SAFE_FREE(key_blob);
      SAFE_FREE(file_content);
      return SET_ERRNO(ERROR_CRYPTO_KEY, "Decrypted key truncated at pubkey length: %s", key_path);
    }
    uint32_t pubkey_data_len = read_u32_be(&decrypted_blob[dec_offset]);
    dec_offset += 4;
 
    // Read public key (32 bytes for Ed25519)
    if (pubkey_data_len != 32) {
      SAFE_FREE(decrypted_blob);
      SAFE_FREE(key_blob);
      SAFE_FREE(file_content);
      return SET_ERRNO(ERROR_CRYPTO_KEY, "Invalid Ed25519 public key length: %u (expected 32)", pubkey_data_len);
    }
    if (dec_offset + pubkey_data_len > decrypted_blob_len) {
      SAFE_FREE(decrypted_blob);
      SAFE_FREE(key_blob);
      SAFE_FREE(file_content);
      return SET_ERRNO(ERROR_CRYPTO_KEY, "Decrypted key truncated at pubkey data: %s", key_path);
    }
    uint8_t ed25519_pk[32];
    memcpy(ed25519_pk, decrypted_blob + dec_offset, 32);
    dec_offset += 32;
 
    // Read private key length
    if (dec_offset + 4 > decrypted_blob_len) {
      SAFE_FREE(decrypted_blob);
      SAFE_FREE(key_blob);
      SAFE_FREE(file_content);
      return SET_ERRNO(ERROR_CRYPTO_KEY, "Decrypted key truncated at privkey length: %s", key_path);
    }
    uint32_t privkey_data_len = read_u32_be(&decrypted_blob[dec_offset]);
    dec_offset += 4;
 
    // Read private key (64 bytes for Ed25519: 32-byte seed + 32-byte public key)
    if (privkey_data_len != 64) {
      SAFE_FREE(decrypted_blob);
      SAFE_FREE(key_blob);
      SAFE_FREE(file_content);
      return SET_ERRNO(ERROR_CRYPTO_KEY, "Invalid Ed25519 private key length: %u (expected 64)", privkey_data_len);
    }
    if (dec_offset + privkey_data_len > decrypted_blob_len) {
      SAFE_FREE(decrypted_blob);
      SAFE_FREE(key_blob);
      SAFE_FREE(file_content);
      return SET_ERRNO(ERROR_CRYPTO_KEY, "Decrypted key truncated at privkey data: %s", key_path);
    }
    uint8_t ed25519_sk[64];
    memcpy(ed25519_sk, decrypted_blob + dec_offset, 64);
    dec_offset += 64;
 
    // Populate key_out (ed25519_sk contains: 32-byte seed + 32-byte public key)
    key_out->type = KEY_TYPE_ED25519;
    memcpy(key_out->key.ed25519, ed25519_sk, 32);           // Seed (first 32 bytes)
    memcpy(key_out->key.ed25519 + 32, ed25519_sk + 32, 32); // Public key (next 32 bytes)
 
    // Clean up decrypted data (sensitive!)
    sodium_memzero(decrypted_blob, decrypted_blob_len);
    SAFE_FREE(decrypted_blob);
    SAFE_FREE(key_blob);
    SAFE_FREE(file_content);
 
    log_debug("Successfully parsed decrypted Ed25519 key");
 
    // Attempt to add the decrypted key to ssh-agent for future password-free use
    log_debug("Attempting to add decrypted key to ssh-agent");
    asciichat_error_t agent_result = ssh_agent_add_key(key_out, key_path);
    if (agent_result == ASCIICHAT_OK) {
      log_debug("Successfully added key to ssh-agent - password will not be required on next run");
    } else {
      // Non-fatal: key is already decrypted and loaded, just won't be cached in agent
      log_warn("Failed to add key to ssh-agent (non-fatal): %s", asciichat_error_string(agent_result));
      log_warn("You can manually add it with: ssh-add %s", key_path);
    }
 
    return ASCIICHAT_OK;
  }
 
  // Read number of keys
  if (offset + 4 > key_blob_len) {
    SAFE_FREE(key_blob);
    SAFE_FREE(file_content);
    return SET_ERRNO(ERROR_CRYPTO_KEY, "OpenSSH private key truncated at num keys: %s", key_path);
  }
 
  uint32_t num_keys = read_u32_be(&key_blob[offset]);
  offset += 4;
 
  log_debug("num_keys=%u, offset=%zu, key_blob_len=%zu", num_keys, offset, key_blob_len);
  log_debug("Raw bytes at offset %zu: %02x %02x %02x %02x", offset, key_blob[offset], key_blob[offset + 1],
            key_blob[offset + 2], key_blob[offset + 3]);
  log_debug("After num_keys, offset=%zu", offset);
 
  if (num_keys != 1) {
    SAFE_FREE(key_blob);
    SAFE_FREE(file_content);
    return SET_ERRNO(ERROR_CRYPTO_KEY, "OpenSSH private key contains %u keys (expected 1): %s", num_keys, key_path);
  }
 
  // Read public key
  if (offset + 4 > key_blob_len) {
    SAFE_FREE(key_blob);
    SAFE_FREE(file_content);
    return SET_ERRNO(ERROR_CRYPTO_KEY, "OpenSSH private key truncated at pubkey length: %s", key_path);
  }
 
  log_debug("About to read pubkey_len at offset=%zu, bytes: %02x %02x %02x %02x", offset, key_blob[offset],
            key_blob[offset + 1], key_blob[offset + 2], key_blob[offset + 3]);
 
  uint32_t pubkey_len = read_u32_be(&key_blob[offset]);
  offset += 4;
 
  log_debug("pubkey_len=%u, offset=%zu", pubkey_len, offset);
 
  if (offset + pubkey_len > key_blob_len) {
    SAFE_FREE(key_blob);
    SAFE_FREE(file_content);
    return SET_ERRNO(ERROR_CRYPTO_KEY, "OpenSSH private key truncated at pubkey data: %s", key_path);
  }
 
  // Parse the public key to extract the Ed25519 public key for validation
  if (pubkey_len < 4) {
    SAFE_FREE(key_blob);
    SAFE_FREE(file_content);
    return SET_ERRNO(ERROR_CRYPTO_KEY, "OpenSSH public key too small: %s", key_path);
  }
 
  uint32_t key_type_len = read_u32_be(&key_blob[offset]);
  offset += 4;
 
  // Check if it's an Ed25519 key
  if (key_type_len != 11 || memcmp(key_blob + offset, "ssh-ed25519", 11) != 0) {
    SAFE_FREE(key_blob);
    SAFE_FREE(file_content);
    return SET_ERRNO(ERROR_CRYPTO_KEY, "OpenSSH private key is not Ed25519: %s", key_path);
  }
 
  offset += key_type_len; // Skip the key type string
  log_debug("After skipping key type, offset=%zu", offset);
 
  // Read the public key length
  if (offset + 4 > key_blob_len) {
    SAFE_FREE(key_blob);
    SAFE_FREE(file_content);
    return SET_ERRNO(ERROR_CRYPTO_KEY, "OpenSSH private key truncated at public key length: %s", key_path);
  }
 
  uint32_t pubkey_data_len = read_u32_be(&key_blob[offset]);
  offset += 4;
  log_debug("Public key data length: %u, offset=%zu", pubkey_data_len, offset);
 
  log_debug("Public key data length: %u (expected 32 for Ed25519)", pubkey_data_len);
 
  // For Ed25519, the public key should be 32 bytes, but let's be more flexible
  if (pubkey_data_len < 32) {
    SAFE_FREE(key_blob);
    SAFE_FREE(file_content);
    return SET_ERRNO(ERROR_CRYPTO_KEY, "OpenSSH public key data too small (%u bytes, expected at least 32): %s",
                     pubkey_data_len, key_path);
  }
 
  // Read Ed25519 public key (first 32 bytes) for validation
  if (offset + 32 > key_blob_len) {
    SAFE_FREE(key_blob);
    SAFE_FREE(file_content);
    return SET_ERRNO(ERROR_CRYPTO_KEY, "OpenSSH private key truncated at public key: %s", key_path);
  }
 
  uint8_t ed25519_pubkey[32];
  memcpy(ed25519_pubkey, key_blob + offset, 32);
  offset += pubkey_data_len; // Skip the entire public key data
 
  // Skip the rest of the public key data to get to the private key
  // We've already parsed: 4 (key_type_len) + 11 (ssh-ed25519) + 4 (pubkey_data_len) + 32 (key) = 51 bytes
  // So we need to skip the remaining pubkey_len - 51 bytes
  // Check for underflow before subtraction
  if (pubkey_len >= 51) {
    size_t remaining_pubkey = pubkey_len - 51;
    if (remaining_pubkey > 0) {
      offset += remaining_pubkey;
    }
  }
 
  // Read private key
  if (offset + 4 > key_blob_len) {
    SAFE_FREE(key_blob);
    SAFE_FREE(file_content);
    return SET_ERRNO(ERROR_CRYPTO_KEY, "OpenSSH private key truncated at privkey length: %s", key_path);
  }
 
  uint32_t privkey_len = read_u32_be(&key_blob[offset]);
  offset += 4;
 
  if (offset + privkey_len > key_blob_len) {
    SAFE_FREE(key_blob);
    SAFE_FREE(file_content);
    return SET_ERRNO(ERROR_CRYPTO_KEY, "OpenSSH private key truncated at privkey data: %s", key_path);
  }
 
  // Parse the private key structure
  // Format: [4 bytes: checkint1] [4 bytes: checkint2] [4 bytes: key type length] [key type]
  //         [4 bytes: public key length] [public key] [4 bytes: private key length] [private key]
  //         [4 bytes: comment length] [comment]
 
  if (privkey_len < 8) {
    SAFE_FREE(key_blob);
    SAFE_FREE(file_content);
    return SET_ERRNO(ERROR_CRYPTO_KEY, "OpenSSH private key data too small: %s", key_path);
  }
 
  // Verify checkints (should be equal)
  uint32_t checkint1 = read_u32_be(&key_blob[offset]);
  uint32_t checkint2 = read_u32_be(&key_blob[offset + 4]);
  offset += 8;
 
  if (checkint1 != checkint2) {
    SAFE_FREE(key_blob);
    SAFE_FREE(file_content);
    return SET_ERRNO(ERROR_CRYPTO_KEY, "OpenSSH private key checkints don't match: %s", key_path);
  }
 
  // Skip key type
  if (offset + 4 > key_blob_len) {
    SAFE_FREE(key_blob);
    SAFE_FREE(file_content);
    return SET_ERRNO(ERROR_CRYPTO_KEY, "OpenSSH private key truncated at key type length: %s", key_path);
  }
 
  uint32_t key_type_len_priv = read_u32_be(&key_blob[offset]);
  // Check for integer overflow before adding to offset
  if (key_type_len_priv > key_blob_len || offset + 4 + key_type_len_priv > key_blob_len) {
    SAFE_FREE(key_blob);
    SAFE_FREE(file_content);
    return SET_ERRNO(ERROR_CRYPTO_KEY, "OpenSSH private key type length overflow: %u", key_type_len_priv);
  }
  offset += 4 + key_type_len_priv;
 
  // Skip public key
  if (offset + 4 > key_blob_len) {
    SAFE_FREE(key_blob);
    SAFE_FREE(file_content);
    return SET_ERRNO(ERROR_CRYPTO_KEY, "OpenSSH private key truncated at pubkey length: %s", key_path);
  }
 
  uint32_t pubkey_len_priv = read_u32_be(&key_blob[offset]);
  // Check for integer overflow before adding to offset
  if (pubkey_len_priv > key_blob_len || offset + 4 + pubkey_len_priv > key_blob_len) {
    SAFE_FREE(key_blob);
    SAFE_FREE(file_content);
    return SET_ERRNO(ERROR_CRYPTO_KEY, "OpenSSH private key public key length overflow: %u", pubkey_len_priv);
  }
  offset += 4 + pubkey_len_priv;
 
  // Read private key
  if (offset + 4 > key_blob_len) {
    SAFE_FREE(key_blob);
    SAFE_FREE(file_content);
    return SET_ERRNO(ERROR_CRYPTO_KEY, "OpenSSH private key truncated at privkey length: %s", key_path);
  }
 
  uint32_t privkey_data_len = read_u32_be(&key_blob[offset]);
  offset += 4;
 
  if (offset + privkey_data_len > key_blob_len) {
    SAFE_FREE(key_blob);
    SAFE_FREE(file_content);
    return SET_ERRNO(ERROR_CRYPTO_KEY, "OpenSSH private key truncated at privkey data: %s", key_path);
  }
 
  // The private key data should be at least 64 bytes (32 bytes private key + 32 bytes public key)
  // But OpenSSH format may have additional data
  if (privkey_data_len < 64) {
    SAFE_FREE(key_blob);
    SAFE_FREE(file_content);
    return SET_ERRNO(ERROR_CRYPTO_KEY, "OpenSSH private key data length is %u (expected at least 64): %s",
                     privkey_data_len, key_path);
  }
 
  // Extract the Ed25519 private key (first 32 bytes)
  uint8_t ed25519_privkey[32];
  memcpy(ed25519_privkey, key_blob + offset, 32);
 
  // Verify the public key matches
  // The public key in the privkey section is raw Ed25519, while the one in pubkey section is SSH format
  // We need to compare the raw public key from privkey with the raw public key extracted from pubkey
  // Use constant-time comparison for cryptographic material
  if (sodium_memcmp(key_blob + offset + 32, ed25519_pubkey, 32) != 0) {
    SAFE_FREE(key_blob);
    SAFE_FREE(file_content);
    return SET_ERRNO(ERROR_CRYPTO_KEY, "OpenSSH private key public key mismatch: %s", key_path);
  }
 
  // Initialize the private key structure
  memset(key_out, 0, sizeof(private_key_t));
  key_out->type = KEY_TYPE_ED25519;
 
  // Store the actual private key (seed + public key = 64 bytes)
  // Ed25519 private key format: [32 bytes seed][32 bytes public key]
  memcpy(key_out->key.ed25519, ed25519_privkey, 32);     // Store the seed (first 32 bytes)
  memcpy(key_out->key.ed25519 + 32, ed25519_pubkey, 32); // Store the public key (next 32 bytes)
 
  // Also store the public key in the public_key field for easy access
  memcpy(key_out->public_key, ed25519_pubkey, 32);
 
  // Set a comment
  SAFE_STRNCPY(key_out->key_comment, "ssh-ed25519", sizeof(key_out->key_comment) - 1);
 
  SAFE_FREE(key_blob);
  SAFE_FREE(file_content);
 
  return ASCIICHAT_OK;
}

References crypto_regex_extract_pem_base64(), parse_ssh_ed25519_line(), platform_fopen(), platform_getenv(), platform_strdup(), prompt_password_simple(), safe_snprintf(), ssh_agent_add_key(), ssh_agent_has_key(), and validate_ssh_key_file().

Referenced by parse_private_key().

validate_ssh_key_file()

asciichat_error_t validate_ssh_key_file

(

const char *

key_path

)

Definition at line 940 of file ssh_keys.c.

                                                              {
  if (!key_path) {
    return SET_ERRNO(ERROR_INVALID_PARAM, "Invalid parameters: key_path=%p", key_path);
  }
 
  if (!path_looks_like_path(key_path)) {
    return SET_ERRNO(ERROR_CRYPTO_KEY, "Invalid SSH key path: %s", key_path);
  }
 
  char *normalized_path = NULL;
  asciichat_error_t path_result = path_validate_user_path(key_path, PATH_ROLE_KEY_PRIVATE, &normalized_path);
  if (path_result != ASCIICHAT_OK) {
    SAFE_FREE(normalized_path);
    return path_result;
  }
 
  // Check if file exists and is readable
  FILE *test_file = platform_fopen(normalized_path, "r");
  if (test_file == NULL) {
    SAFE_FREE(normalized_path);
    return SET_ERRNO(ERROR_CRYPTO_KEY, "Cannot read key file: %s", key_path);
  }
 
  // Check if this is an SSH key file or GPG armored key by looking for the header
  char header[BUFFER_SIZE_SMALL];
  bool is_valid_key_file = false;
  if (fgets(header, sizeof(header), test_file) != NULL) {
    if (strstr(header, "BEGIN OPENSSH PRIVATE KEY") != NULL || strstr(header, "BEGIN RSA PRIVATE KEY") != NULL ||
        strstr(header, "BEGIN EC PRIVATE KEY") != NULL || strstr(header, "BEGIN PGP PRIVATE KEY") != NULL ||
        strstr(header, "BEGIN PGP SECRET KEY") != NULL) {
      is_valid_key_file = true;
    }
  }
  (void)fclose(test_file);
 
  if (!is_valid_key_file) {
    SAFE_FREE(normalized_path);
    return SET_ERRNO(ERROR_CRYPTO_KEY, "File is not a valid SSH or GPG key: %s", key_path);
  }
 
  // Check permissions for SSH key files (should be 600 or 400)
#ifndef _WIN32
  struct stat st;
  if (stat(normalized_path, &st) == 0) {
    if ((st.st_mode & SSH_KEY_PERMISSIONS_MASK) != 0) {
      log_error("SSH key file %s has overly permissive permissions: %o", key_path, st.st_mode & 0777);
      log_error("Run 'chmod 600 %s' to fix this", key_path);
      SAFE_FREE(normalized_path);
      return SET_ERRNO(ERROR_CRYPTO_KEY, "SSH key file has overly permissive permissions: %s", key_path);
    }
  }
#endif
 
  SAFE_FREE(normalized_path);
  return ASCIICHAT_OK;
}

References path_looks_like_path(), path_validate_user_path(), and platform_fopen().

Referenced by client_crypto_init(), and parse_ssh_private_key().