import * as bigInt from "big-integer";
import { Observable, firstValueFrom, map } from "rxjs";

import { EncryptedOrganizationKeyData } from "../../admin-console/models/data/encrypted-organization-key.data";
import { ProfileOrganizationResponse } from "../../admin-console/models/response/profile-organization.response";
import { ProfileProviderOrganizationResponse } from "../../admin-console/models/response/profile-provider-organization.response";
import { ProfileProviderResponse } from "../../admin-console/models/response/profile-provider.response";
import { AccountService } from "../../auth/abstractions/account.service";
import { AuthenticationStatus } from "../../auth/enums/authentication-status";
import { KdfConfig } from "../../auth/models/domain/kdf-config";
import { Utils } from "../../platform/misc/utils";
import { OrganizationId, ProviderId, UserId } from "../../types/guid";
import {
  OrgKey,
  UserKey,
  MasterKey,
  ProviderKey,
  PinKey,
  CipherKey,
  UserPrivateKey,
  UserPublicKey,
} from "../../types/key";
import { CryptoFunctionService } from "../abstractions/crypto-function.service";
import { CryptoService as CryptoServiceAbstraction } from "../abstractions/crypto.service";
import { EncryptService } from "../abstractions/encrypt.service";
import { LogService } from "../abstractions/log.service";
import { PlatformUtilsService } from "../abstractions/platform-utils.service";
import { StateService } from "../abstractions/state.service";
import {
  KeySuffixOptions,
  HashPurpose,
  KdfType,
  ARGON2_ITERATIONS,
  ARGON2_MEMORY,
  ARGON2_PARALLELISM,
  EncryptionType,
  PBKDF2_ITERATIONS,
} from "../enums";
import { sequentialize } from "../misc/sequentialize";
import { EFFLongWordList } from "../misc/wordlist";
import { EncArrayBuffer } from "../models/domain/enc-array-buffer";
import { EncString, EncryptedString } from "../models/domain/enc-string";
import { SymmetricCryptoKey } from "../models/domain/symmetric-crypto-key";
import { ActiveUserState, DerivedState, StateProvider } from "../state";

import {
  USER_ENCRYPTED_ORGANIZATION_KEYS,
  USER_ORGANIZATION_KEYS,
} from "./key-state/org-keys.state";
import { USER_ENCRYPTED_PROVIDER_KEYS, USER_PROVIDER_KEYS } from "./key-state/provider-keys.state";
import {
  USER_ENCRYPTED_PRIVATE_KEY,
  USER_EVER_HAD_USER_KEY,
  USER_PRIVATE_KEY,
  USER_PUBLIC_KEY,
  USER_KEY,
} from "./key-state/user-key.state";

export class CryptoService implements CryptoServiceAbstraction {
  private readonly activeUserKeyState: ActiveUserState<UserKey>;
  private readonly activeUserEverHadUserKey: ActiveUserState<boolean>;
  private readonly activeUserEncryptedOrgKeysState: ActiveUserState<
    Record<OrganizationId, EncryptedOrganizationKeyData>
  >;
  private readonly activeUserOrgKeysState: DerivedState<Record<OrganizationId, OrgKey>>;
  private readonly activeUserEncryptedProviderKeysState: ActiveUserState<
    Record<ProviderId, EncryptedString>
  >;
  private readonly activeUserProviderKeysState: DerivedState<Record<ProviderId, ProviderKey>>;
  private readonly activeUserEncryptedPrivateKeyState: ActiveUserState<EncryptedString>;
  private readonly activeUserPrivateKeyState: DerivedState<UserPrivateKey>;
  private readonly activeUserPublicKeyState: DerivedState<UserPublicKey>;

  readonly activeUserKey$: Observable<UserKey>;

  readonly activeUserOrgKeys$: Observable<Record<OrganizationId, OrgKey>>;
  readonly activeUserProviderKeys$: Observable<Record<ProviderId, ProviderKey>>;
  readonly activeUserPrivateKey$: Observable<UserPrivateKey>;
  readonly activeUserPublicKey$: Observable<UserPublicKey>;
  readonly everHadUserKey$: Observable<boolean>;

  constructor(
    protected cryptoFunctionService: CryptoFunctionService,
    protected encryptService: EncryptService,
    protected platformUtilService: PlatformUtilsService,
    protected logService: LogService,
    protected stateService: StateService,
    protected accountService: AccountService,
    protected stateProvider: StateProvider,
  ) {
    // User Key
    this.activeUserKeyState = stateProvider.getActive(USER_KEY);
    this.activeUserKey$ = this.activeUserKeyState.state$;
    this.activeUserEverHadUserKey = stateProvider.getActive(USER_EVER_HAD_USER_KEY);
    this.everHadUserKey$ = this.activeUserEverHadUserKey.state$.pipe(map((x) => x ?? false));

    // User Asymmetric Key Pair
    this.activeUserEncryptedPrivateKeyState = stateProvider.getActive(USER_ENCRYPTED_PRIVATE_KEY);
    this.activeUserPrivateKeyState = stateProvider.getDerived(
      this.activeUserEncryptedPrivateKeyState.combinedState$,
      USER_PRIVATE_KEY,
      {
        encryptService: this.encryptService,
        cryptoService: this,
      },
    );
    this.activeUserPrivateKey$ = this.activeUserPrivateKeyState.state$; // may be null
    this.activeUserPublicKeyState = stateProvider.getDerived(
      this.activeUserPrivateKey$,
      USER_PUBLIC_KEY,
      {
        cryptoFunctionService: this.cryptoFunctionService,
      },
    );
    this.activeUserPublicKey$ = this.activeUserPublicKeyState.state$; // may be null

    // Organization keys
    this.activeUserEncryptedOrgKeysState = stateProvider.getActive(
      USER_ENCRYPTED_ORGANIZATION_KEYS,
    );
    this.activeUserOrgKeysState = stateProvider.getDerived(
      this.activeUserEncryptedOrgKeysState.state$,
      USER_ORGANIZATION_KEYS,
      { cryptoService: this },
    );
    this.activeUserOrgKeys$ = this.activeUserOrgKeysState.state$; // null handled by `derive` function

    // Provider keys
    this.activeUserEncryptedProviderKeysState = stateProvider.getActive(
      USER_ENCRYPTED_PROVIDER_KEYS,
    );
    this.activeUserProviderKeysState = stateProvider.getDerived(
      this.activeUserEncryptedProviderKeysState.state$,
      USER_PROVIDER_KEYS,
      { encryptService: this.encryptService, cryptoService: this },
    );
    this.activeUserProviderKeys$ = this.activeUserProviderKeysState.state$; // null handled by `derive` function
  }

  async setUserKey(key: UserKey, userId?: UserId): Promise<void> {
    if (key == null) {
      throw new Error("No key provided. Use ClearUserKey to clear the key");
    }
    // Set userId to ensure we have one for the account status update
    [userId, key] = await this.stateProvider.setUserState(USER_KEY, key, userId);
    await this.stateProvider.setUserState(USER_EVER_HAD_USER_KEY, true, userId);

    await this.accountService.setAccountStatus(userId, AuthenticationStatus.Unlocked);

    await this.storeAdditionalKeys(key, userId);
  }

  async refreshAdditionalKeys(): Promise<void> {
    const key = await this.getUserKey();
    await this.setUserKey(key);
  }

  async getUserKey(userId?: UserId): Promise<UserKey> {
    let userKey = await firstValueFrom(this.stateProvider.getUserState$(USER_KEY, userId));
    if (userKey) {
      return userKey;
    }

    // If the user has set their vault timeout to 'Never', we can load the user key from storage
    if (await this.hasUserKeyStored(KeySuffixOptions.Auto, userId)) {
      userKey = await this.getKeyFromStorage(KeySuffixOptions.Auto, userId);
      if (userKey) {
        await this.setUserKey(userKey, userId);
        return userKey;
      }
    }
  }

  async isLegacyUser(masterKey?: MasterKey, userId?: UserId): Promise<boolean> {
    return await this.validateUserKey(
      (masterKey ?? (await this.getMasterKey(userId))) as unknown as UserKey,
    );
  }

  async getUserKeyWithLegacySupport(userId?: UserId): Promise<UserKey> {
    const userKey = await this.getUserKey(userId);
    if (userKey) {
      return userKey;
    }

    // Legacy support: encryption used to be done with the master key (derived from master password).
    // Users who have not migrated will have a null user key and must use the master key instead.
    return (await this.getMasterKey(userId)) as unknown as UserKey;
  }

  async getUserKeyFromStorage(keySuffix: KeySuffixOptions, userId?: UserId): Promise<UserKey> {
    const userKey = await this.getKeyFromStorage(keySuffix, userId);
    if (userKey) {
      if (!(await this.validateUserKey(userKey))) {
        this.logService.warning("Invalid key, throwing away stored keys");
        await this.clearAllStoredUserKeys(userId);
      }
      return userKey;
    }
  }

  async hasUserKey(): Promise<boolean> {
    return (
      (await this.hasUserKeyInMemory()) || (await this.hasUserKeyStored(KeySuffixOptions.Auto))
    );
  }

  async hasUserKeyInMemory(userId?: UserId): Promise<boolean> {
    return (await firstValueFrom(this.stateProvider.getUserState$(USER_KEY, userId))) != null;
  }

  async hasUserKeyStored(keySuffix: KeySuffixOptions, userId?: UserId): Promise<boolean> {
    return (await this.getKeyFromStorage(keySuffix, userId)) != null;
  }

  async makeUserKey(masterKey: MasterKey): Promise<[UserKey, EncString]> {
    masterKey ||= await this.getMasterKey();
    if (masterKey == null) {
      throw new Error("No Master Key found.");
    }

    const newUserKey = await this.cryptoFunctionService.aesGenerateKey(512);
    return this.buildProtectedSymmetricKey(masterKey, newUserKey);
  }

  async clearUserKey(clearStoredKeys = true, userId?: UserId): Promise<void> {
    // Set userId to ensure we have one for the account status update
    [userId] = await this.stateProvider.setUserState(USER_KEY, null, userId);
    await this.accountService.setMaxAccountStatus(userId, AuthenticationStatus.Locked);
    if (clearStoredKeys) {
      await this.clearAllStoredUserKeys(userId);
    }
  }

  async clearStoredUserKey(keySuffix: KeySuffixOptions, userId?: UserId): Promise<void> {
    if (keySuffix === KeySuffixOptions.Auto) {
      // FIXME: Verify that this floating promise is intentional. If it is, add an explanatory comment and ensure there is proper error handling.
      // eslint-disable-next-line @typescript-eslint/no-floating-promises
      this.stateService.setUserKeyAutoUnlock(null, { userId: userId });
      // FIXME: Verify that this floating promise is intentional. If it is, add an explanatory comment and ensure there is proper error handling.
      // eslint-disable-next-line @typescript-eslint/no-floating-promises
      this.clearDeprecatedKeys(KeySuffixOptions.Auto, userId);
    }
    if (keySuffix === KeySuffixOptions.Pin) {
      // FIXME: Verify that this floating promise is intentional. If it is, add an explanatory comment and ensure there is proper error handling.
      // eslint-disable-next-line @typescript-eslint/no-floating-promises
      this.stateService.setPinKeyEncryptedUserKeyEphemeral(null, { userId: userId });
      // FIXME: Verify that this floating promise is intentional. If it is, add an explanatory comment and ensure there is proper error handling.
      // eslint-disable-next-line @typescript-eslint/no-floating-promises
      this.clearDeprecatedKeys(KeySuffixOptions.Pin, userId);
    }
  }

  async setMasterKeyEncryptedUserKey(userKeyMasterKey: string, userId?: UserId): Promise<void> {
    await this.stateService.setMasterKeyEncryptedUserKey(userKeyMasterKey, { userId: userId });
  }

  async setMasterKey(key: MasterKey, userId?: UserId): Promise<void> {
    await this.stateService.setMasterKey(key, { userId: userId });
  }

  async getMasterKey(userId?: UserId): Promise<MasterKey> {
    let masterKey = await this.stateService.getMasterKey({ userId: userId });
    if (!masterKey) {
      masterKey = (await this.stateService.getCryptoMasterKey({ userId: userId })) as MasterKey;
      // if master key was null/undefined and getCryptoMasterKey also returned null/undefined,
      // don't set master key as it is unnecessary
      if (masterKey) {
        await this.setMasterKey(masterKey, userId);
      }
    }
    return masterKey;
  }

  async getOrDeriveMasterKey(password: string, userId?: UserId) {
    let masterKey = await this.getMasterKey(userId);
    return (masterKey ||= await this.makeMasterKey(
      password,
      await this.stateService.getEmail({ userId: userId }),
      await this.stateService.getKdfType({ userId: userId }),
      await this.stateService.getKdfConfig({ userId: userId }),
    ));
  }

  /**
   * Derive a master key from a password and email.
   *
   * @remarks
   * Does not validate the kdf config to ensure it satisfies the minimum requirements for the given kdf type.
   */
  async makeMasterKey(
    password: string,
    email: string,
    kdf: KdfType,
    KdfConfig: KdfConfig,
  ): Promise<MasterKey> {
    return (await this.makeKey(password, email, kdf, KdfConfig)) as MasterKey;
  }

  async clearMasterKey(userId?: UserId): Promise<void> {
    await this.stateService.setMasterKey(null, { userId: userId });
  }

  async encryptUserKeyWithMasterKey(
    masterKey: MasterKey,
    userKey?: UserKey,
  ): Promise<[UserKey, EncString]> {
    userKey ||= await this.getUserKey();
    return await this.buildProtectedSymmetricKey(masterKey, userKey.key);
  }

  async decryptUserKeyWithMasterKey(
    masterKey: MasterKey,
    userKey?: EncString,
    userId?: UserId,
  ): Promise<UserKey> {
    masterKey ||= await this.getMasterKey(userId);
    if (masterKey == null) {
      throw new Error("No master key found.");
    }

    if (!userKey) {
      let masterKeyEncryptedUserKey = await this.stateService.getMasterKeyEncryptedUserKey({
        userId: userId,
      });

      // Try one more way to get the user key if it still wasn't found.
      if (masterKeyEncryptedUserKey == null) {
        masterKeyEncryptedUserKey = await this.stateService.getEncryptedCryptoSymmetricKey({
          userId: userId,
        });
      }

      if (masterKeyEncryptedUserKey == null) {
        throw new Error("No encrypted user key found.");
      }
      userKey = new EncString(masterKeyEncryptedUserKey);
    }

    let decUserKey: Uint8Array;
    if (userKey.encryptionType === EncryptionType.AesCbc256_B64) {
      decUserKey = await this.encryptService.decryptToBytes(userKey, masterKey);
    } else if (userKey.encryptionType === EncryptionType.AesCbc256_HmacSha256_B64) {
      const newKey = await this.stretchKey(masterKey);
      decUserKey = await this.encryptService.decryptToBytes(userKey, newKey);
    } else {
      throw new Error("Unsupported encryption type.");
    }
    if (decUserKey == null) {
      return null;
    }

    return new SymmetricCryptoKey(decUserKey) as UserKey;
  }

  async hashMasterKey(
    password: string,
    key: MasterKey,
    hashPurpose?: HashPurpose,
  ): Promise<string> {
    key ||= await this.getMasterKey();

    if (password == null || key == null) {
      throw new Error("Invalid parameters.");
    }

    const iterations = hashPurpose === HashPurpose.LocalAuthorization ? 2 : 1;
    const hash = await this.cryptoFunctionService.pbkdf2(key.key, password, "sha256", iterations);
    return Utils.fromBufferToB64(hash);
  }

  async setMasterKeyHash(keyHash: string): Promise<void> {
    await this.stateService.setKeyHash(keyHash);
  }

  async getMasterKeyHash(): Promise<string> {
    return await this.stateService.getKeyHash();
  }

  async clearMasterKeyHash(userId?: UserId): Promise<void> {
    return await this.stateService.setKeyHash(null, { userId: userId });
  }

  async compareAndUpdateKeyHash(masterPassword: string, masterKey: MasterKey): Promise<boolean> {
    const storedPasswordHash = await this.getMasterKeyHash();
    if (masterPassword != null && storedPasswordHash != null) {
      const localKeyHash = await this.hashMasterKey(
        masterPassword,
        masterKey,
        HashPurpose.LocalAuthorization,
      );
      if (localKeyHash != null && storedPasswordHash === localKeyHash) {
        return true;
      }

      // TODO: remove serverKeyHash check in 1-2 releases after everyone's keyHash has been updated
      const serverKeyHash = await this.hashMasterKey(
        masterPassword,
        masterKey,
        HashPurpose.ServerAuthorization,
      );
      if (serverKeyHash != null && storedPasswordHash === serverKeyHash) {
        await this.setMasterKeyHash(localKeyHash);
        return true;
      }
    }

    return false;
  }

  async setOrgKeys(
    orgs: ProfileOrganizationResponse[] = [],
    providerOrgs: ProfileProviderOrganizationResponse[] = [],
  ): Promise<void> {
    // FIXME: Verify that this floating promise is intentional. If it is, add an explanatory comment and ensure there is proper error handling.
    // eslint-disable-next-line @typescript-eslint/no-floating-promises
    this.activeUserEncryptedOrgKeysState.update((_) => {
      const encOrgKeyData: { [orgId: string]: EncryptedOrganizationKeyData } = {};

      orgs.forEach((org) => {
        encOrgKeyData[org.id] = {
          type: "organization",
          key: org.key,
        };
      });

      providerOrgs.forEach((org) => {
        encOrgKeyData[org.id] = {
          type: "provider",
          providerId: org.providerId,
          key: org.key,
        };
      });

      return encOrgKeyData;
    });
  }

  async getOrgKey(orgId: OrganizationId): Promise<OrgKey> {
    return (await firstValueFrom(this.activeUserOrgKeys$))[orgId];
  }

  @sequentialize(() => "getOrgKeys")
  async getOrgKeys(): Promise<Record<string, OrgKey>> {
    return await firstValueFrom(this.activeUserOrgKeys$);
  }

  async makeDataEncKey<T extends OrgKey | UserKey>(
    key: T,
  ): Promise<[SymmetricCryptoKey, EncString]> {
    if (key == null) {
      throw new Error("No key provided");
    }

    const newSymKey = await this.cryptoFunctionService.aesGenerateKey(512);
    return this.buildProtectedSymmetricKey(key, newSymKey);
  }

  async clearOrgKeys(memoryOnly?: boolean, userId?: UserId): Promise<void> {
    const activeUserId = (await firstValueFrom(this.accountService.activeAccount$))?.id;
    const userIdIsActive = userId == null || userId === activeUserId;
    if (memoryOnly && userIdIsActive) {
      // org keys are only cached for active users
      await this.activeUserOrgKeysState.forceValue({});
    } else {
      if (userId == null && activeUserId == null) {
        // nothing to do
        return;
      }
      await this.stateProvider
        .getUser(userId ?? activeUserId, USER_ENCRYPTED_ORGANIZATION_KEYS)
        .update(() => null);
    }
  }

  async setProviderKeys(providers: ProfileProviderResponse[]): Promise<void> {
    // FIXME: Verify that this floating promise is intentional. If it is, add an explanatory comment and ensure there is proper error handling.
    // eslint-disable-next-line @typescript-eslint/no-floating-promises
    this.activeUserEncryptedProviderKeysState.update((_) => {
      const encProviderKeys: { [providerId: ProviderId]: EncryptedString } = {};

      providers.forEach((provider) => {
        encProviderKeys[provider.id as ProviderId] = provider.key as EncryptedString;
      });

      return encProviderKeys;
    });
  }

  async getProviderKey(providerId: ProviderId): Promise<ProviderKey> {
    if (providerId == null) {
      return null;
    }

    return (await firstValueFrom(this.activeUserProviderKeys$))[providerId] ?? null;
  }

  @sequentialize(() => "getProviderKeys")
  async getProviderKeys(): Promise<Record<ProviderId, ProviderKey>> {
    return await firstValueFrom(this.activeUserProviderKeys$);
  }

  async clearProviderKeys(memoryOnly?: boolean, userId?: UserId): Promise<void> {
    const activeUserId = (await firstValueFrom(this.accountService.activeAccount$))?.id;
    const userIdIsActive = userId == null || userId === activeUserId;
    if (memoryOnly && userIdIsActive) {
      // provider keys are only cached for active users
      await this.activeUserProviderKeysState.forceValue({});
    } else {
      if (userId == null && activeUserId == null) {
        // nothing to do
        return;
      }
      await this.stateProvider
        .getUser(userId ?? activeUserId, USER_ENCRYPTED_PROVIDER_KEYS)
        .update(() => null);
    }
  }

  async getPublicKey(): Promise<Uint8Array> {
    return await firstValueFrom(this.activeUserPublicKey$);
  }

  async makeOrgKey<T extends OrgKey | ProviderKey>(): Promise<[EncString, T]> {
    const shareKey = await this.cryptoFunctionService.aesGenerateKey(512);
    const publicKey = await this.getPublicKey();
    const encShareKey = await this.rsaEncrypt(shareKey, publicKey);
    return [encShareKey, new SymmetricCryptoKey(shareKey) as T];
  }

  async setPrivateKey(encPrivateKey: EncryptedString): Promise<void> {
    if (encPrivateKey == null) {
      return;
    }

    await this.activeUserEncryptedPrivateKeyState.update(() => encPrivateKey);
  }

  async getPrivateKey(): Promise<Uint8Array> {
    return await firstValueFrom(this.activeUserPrivateKey$);
  }

  async getFingerprint(fingerprintMaterial: string, publicKey?: Uint8Array): Promise<string[]> {
    if (publicKey == null) {
      publicKey = await this.getPublicKey();
    }
    if (publicKey === null) {
      throw new Error("No public key available.");
    }
    const keyFingerprint = await this.cryptoFunctionService.hash(publicKey, "sha256");
    const userFingerprint = await this.cryptoFunctionService.hkdfExpand(
      keyFingerprint,
      fingerprintMaterial,
      32,
      "sha256",
    );
    return this.hashPhrase(userFingerprint);
  }

  async makeKeyPair(key?: SymmetricCryptoKey): Promise<[string, EncString]> {
    // Default to user key
    key ||= await this.getUserKeyWithLegacySupport();

    const keyPair = await this.cryptoFunctionService.rsaGenerateKeyPair(2048);
    const publicB64 = Utils.fromBufferToB64(keyPair[0]);
    const privateEnc = await this.encryptService.encrypt(keyPair[1], key);
    return [publicB64, privateEnc];
  }

  async clearKeyPair(memoryOnly?: boolean, userId?: UserId): Promise<void[]> {
    const activeUserId = (await firstValueFrom(this.accountService.activeAccount$))?.id;
    const userIdIsActive = userId == null || userId === activeUserId;
    if (memoryOnly && userIdIsActive) {
      // key pair is only cached for active users
      await this.activeUserPrivateKeyState.forceValue(null);
      await this.activeUserPublicKeyState.forceValue(null);
      return;
    } else {
      if (userId == null && activeUserId == null) {
        // nothing to do
        return;
      }
      // below updates decrypted private key and public keys if this is the active user as well since those are derived from the encrypted private key
      await this.stateProvider
        .getUser(userId ?? activeUserId, USER_ENCRYPTED_PRIVATE_KEY)
        .update(() => null);
    }
  }

  async makePinKey(pin: string, salt: string, kdf: KdfType, kdfConfig: KdfConfig): Promise<PinKey> {
    const pinKey = await this.makeKey(pin, salt, kdf, kdfConfig);
    return (await this.stretchKey(pinKey)) as PinKey;
  }

  async clearPinKeys(userId?: UserId): Promise<void> {
    await this.stateService.setPinKeyEncryptedUserKey(null, { userId: userId });
    await this.stateService.setPinKeyEncryptedUserKeyEphemeral(null, { userId: userId });
    await this.stateService.setProtectedPin(null, { userId: userId });
    await this.clearDeprecatedKeys(KeySuffixOptions.Pin, userId);
  }

  async decryptUserKeyWithPin(
    pin: string,
    salt: string,
    kdf: KdfType,
    kdfConfig: KdfConfig,
    pinProtectedUserKey?: EncString,
  ): Promise<UserKey> {
    pinProtectedUserKey ||= await this.stateService.getPinKeyEncryptedUserKey();
    pinProtectedUserKey ||= await this.stateService.getPinKeyEncryptedUserKeyEphemeral();
    if (!pinProtectedUserKey) {
      throw new Error("No PIN protected key found.");
    }
    const pinKey = await this.makePinKey(pin, salt, kdf, kdfConfig);
    const userKey = await this.encryptService.decryptToBytes(pinProtectedUserKey, pinKey);
    return new SymmetricCryptoKey(userKey) as UserKey;
  }

  // only for migration purposes
  async decryptMasterKeyWithPin(
    pin: string,
    salt: string,
    kdf: KdfType,
    kdfConfig: KdfConfig,
    pinProtectedMasterKey?: EncString,
  ): Promise<MasterKey> {
    if (!pinProtectedMasterKey) {
      const pinProtectedMasterKeyString = await this.stateService.getEncryptedPinProtected();
      if (pinProtectedMasterKeyString == null) {
        throw new Error("No PIN protected key found.");
      }
      pinProtectedMasterKey = new EncString(pinProtectedMasterKeyString);
    }
    const pinKey = await this.makePinKey(pin, salt, kdf, kdfConfig);
    const masterKey = await this.encryptService.decryptToBytes(pinProtectedMasterKey, pinKey);
    return new SymmetricCryptoKey(masterKey) as MasterKey;
  }

  async makeSendKey(keyMaterial: Uint8Array): Promise<SymmetricCryptoKey> {
    const sendKey = await this.cryptoFunctionService.hkdf(
      keyMaterial,
      "bitwarden-send",
      "send",
      64,
      "sha256",
    );
    return new SymmetricCryptoKey(sendKey);
  }

  async makeCipherKey(): Promise<CipherKey> {
    const randomBytes = await this.cryptoFunctionService.aesGenerateKey(512);
    return new SymmetricCryptoKey(randomBytes) as CipherKey;
  }

  async clearKeys(userId?: UserId): Promise<any> {
    await this.clearUserKey(true, userId);
    await this.clearMasterKeyHash(userId);
    await this.clearOrgKeys(false, userId);
    await this.clearProviderKeys(false, userId);
    await this.clearKeyPair(false, userId);
    await this.clearPinKeys(userId);
    await this.stateProvider.setUserState(USER_EVER_HAD_USER_KEY, null, userId);
  }

  async rsaEncrypt(data: Uint8Array, publicKey?: Uint8Array): Promise<EncString> {
    if (publicKey == null) {
      publicKey = await this.getPublicKey();
    }
    if (publicKey == null) {
      throw new Error("Public key unavailable.");
    }

    const encBytes = await this.cryptoFunctionService.rsaEncrypt(data, publicKey, "sha1");
    return new EncString(EncryptionType.Rsa2048_OaepSha1_B64, Utils.fromBufferToB64(encBytes));
  }

  async rsaDecrypt(encValue: string, privateKeyValue?: Uint8Array): Promise<Uint8Array> {
    const headerPieces = encValue.split(".");
    let encType: EncryptionType = null;
    let encPieces: string[];

    if (headerPieces.length === 1) {
      encType = EncryptionType.Rsa2048_OaepSha256_B64;
      encPieces = [headerPieces[0]];
    } else if (headerPieces.length === 2) {
      try {
        encType = parseInt(headerPieces[0], null);
        encPieces = headerPieces[1].split("|");
      } catch (e) {
        this.logService.error(e);
      }
    }

    switch (encType) {
      case EncryptionType.Rsa2048_OaepSha256_B64:
      case EncryptionType.Rsa2048_OaepSha1_B64:
      case EncryptionType.Rsa2048_OaepSha256_HmacSha256_B64: // HmacSha256 types are deprecated
      case EncryptionType.Rsa2048_OaepSha1_HmacSha256_B64:
        break;
      default:
        throw new Error("encType unavailable.");
    }

    if (encPieces == null || encPieces.length <= 0) {
      throw new Error("encPieces unavailable.");
    }

    const data = Utils.fromB64ToArray(encPieces[0]);
    const privateKey = privateKeyValue ?? (await this.getPrivateKey());
    if (privateKey == null) {
      throw new Error("No private key.");
    }

    let alg: "sha1" | "sha256" = "sha1";
    switch (encType) {
      case EncryptionType.Rsa2048_OaepSha256_B64:
      case EncryptionType.Rsa2048_OaepSha256_HmacSha256_B64:
        alg = "sha256";
        break;
      case EncryptionType.Rsa2048_OaepSha1_B64:
      case EncryptionType.Rsa2048_OaepSha1_HmacSha256_B64:
        break;
      default:
        throw new Error("encType unavailable.");
    }

    return this.cryptoFunctionService.rsaDecrypt(data, privateKey, alg);
  }

  // EFForg/OpenWireless
  // ref https://github.com/EFForg/OpenWireless/blob/master/app/js/diceware.js
  async randomNumber(min: number, max: number): Promise<number> {
    let rval = 0;
    const range = max - min + 1;
    const bitsNeeded = Math.ceil(Math.log2(range));
    if (bitsNeeded > 53) {
      throw new Error("We cannot generate numbers larger than 53 bits.");
    }

    const bytesNeeded = Math.ceil(bitsNeeded / 8);
    const mask = Math.pow(2, bitsNeeded) - 1;
    // 7776 -> (2^13 = 8192) -1 == 8191 or 0x00001111 11111111

    // Fill a byte array with N random numbers
    const byteArray = new Uint8Array(await this.cryptoFunctionService.randomBytes(bytesNeeded));

    let p = (bytesNeeded - 1) * 8;
    for (let i = 0; i < bytesNeeded; i++) {
      rval += byteArray[i] * Math.pow(2, p);
      p -= 8;
    }

    // Use & to apply the mask and reduce the number of recursive lookups
    rval = rval & mask;

    if (rval >= range) {
      // Integer out of acceptable range
      return this.randomNumber(min, max);
    }

    // Return an integer that falls within the range
    return min + rval;
  }

  // ---HELPERS---
  protected async validateUserKey(key: UserKey): Promise<boolean> {
    if (!key) {
      return false;
    }

    try {
      const [userId, encPrivateKey] = await firstValueFrom(
        this.activeUserEncryptedPrivateKeyState.combinedState$,
      );
      if (encPrivateKey == null) {
        return false;
      }

      // Can decrypt private key
      const privateKey = await USER_PRIVATE_KEY.derive([userId, encPrivateKey], {
        encryptService: this.encryptService,
        cryptoService: this,
      });

      // Can successfully derive public key
      await USER_PUBLIC_KEY.derive(privateKey, {
        cryptoFunctionService: this.cryptoFunctionService,
      });
    } catch (e) {
      return false;
    }

    return true;
  }

  /**
   * Initialize all necessary crypto keys needed for a new account.
   * Warning! This completely replaces any existing keys!
   */
  async initAccount(): Promise<{
    userKey: UserKey;
    publicKey: string;
    privateKey: EncString;
  }> {
    const rawKey = await this.cryptoFunctionService.aesGenerateKey(512);
    const userKey = new SymmetricCryptoKey(rawKey) as UserKey;
    const [publicKey, privateKey] = await this.makeKeyPair(userKey);
    await this.setUserKey(userKey);
    await this.activeUserEncryptedPrivateKeyState.update(() => privateKey.encryptedString);

    return {
      userKey,
      publicKey,
      privateKey,
    };
  }

  /**
   * Generates any additional keys if needed. Additional keys are
   * keys such as biometrics, auto, and pin keys.
   * Useful to make sure other keys stay in sync when the user key
   * has been rotated.
   * @param key The user key
   * @param userId The desired user
   */
  protected async storeAdditionalKeys(key: UserKey, userId?: UserId) {
    const storeAuto = await this.shouldStoreKey(KeySuffixOptions.Auto, userId);
    if (storeAuto) {
      await this.stateService.setUserKeyAutoUnlock(key.keyB64, { userId: userId });
    } else {
      await this.stateService.setUserKeyAutoUnlock(null, { userId: userId });
    }
    await this.clearDeprecatedKeys(KeySuffixOptions.Auto, userId);

    const storePin = await this.shouldStoreKey(KeySuffixOptions.Pin, userId);
    if (storePin) {
      await this.storePinKey(key, userId);
      // We can't always clear deprecated keys because the pin is only
      // migrated once used to unlock
      await this.clearDeprecatedKeys(KeySuffixOptions.Pin, userId);
    } else {
      await this.stateService.setPinKeyEncryptedUserKey(null, { userId: userId });
      await this.stateService.setPinKeyEncryptedUserKeyEphemeral(null, { userId: userId });
    }
  }

  /**
   * Stores the pin key if needed. If MP on Reset is enabled, stores the
   * ephemeral version.
   * @param key The user key
   */
  protected async storePinKey(key: UserKey, userId?: UserId) {
    const pin = await this.encryptService.decryptToUtf8(
      new EncString(await this.stateService.getProtectedPin({ userId: userId })),
      key,
    );
    const pinKey = await this.makePinKey(
      pin,
      await this.stateService.getEmail({ userId: userId }),
      await this.stateService.getKdfType({ userId: userId }),
      await this.stateService.getKdfConfig({ userId: userId }),
    );
    const encPin = await this.encryptService.encrypt(key.key, pinKey);

    if ((await this.stateService.getPinKeyEncryptedUserKey({ userId: userId })) != null) {
      await this.stateService.setPinKeyEncryptedUserKey(encPin, { userId: userId });
    } else {
      await this.stateService.setPinKeyEncryptedUserKeyEphemeral(encPin, { userId: userId });
    }
  }

  protected async shouldStoreKey(keySuffix: KeySuffixOptions, userId?: UserId) {
    let shouldStoreKey = false;
    switch (keySuffix) {
      case KeySuffixOptions.Auto: {
        const vaultTimeout = await this.stateService.getVaultTimeout({ userId: userId });
        shouldStoreKey = vaultTimeout == null;
        break;
      }
      case KeySuffixOptions.Pin: {
        const protectedPin = await this.stateService.getProtectedPin({ userId: userId });
        shouldStoreKey = !!protectedPin;
        break;
      }
    }
    return shouldStoreKey;
  }

  protected async getKeyFromStorage(
    keySuffix: KeySuffixOptions,
    userId?: UserId,
  ): Promise<UserKey> {
    if (keySuffix === KeySuffixOptions.Auto) {
      const userKey = await this.stateService.getUserKeyAutoUnlock({ userId: userId });
      if (userKey) {
        return new SymmetricCryptoKey(Utils.fromB64ToArray(userKey)) as UserKey;
      }
    }
    return null;
  }

  /**
   * Validate that the KDF config follows the requirements for the given KDF type.
   *
   * @remarks
   * Should always be called before updating a users KDF config.
   */
  validateKdfConfig(kdf: KdfType, kdfConfig: KdfConfig): void {
    switch (kdf) {
      case KdfType.PBKDF2_SHA256:
        if (!PBKDF2_ITERATIONS.inRange(kdfConfig.iterations)) {
          throw new Error(
            `PBKDF2 iterations must be between ${PBKDF2_ITERATIONS.min} and ${PBKDF2_ITERATIONS.max}`,
          );
        }
        break;
      case KdfType.Argon2id:
        if (!ARGON2_ITERATIONS.inRange(kdfConfig.iterations)) {
          throw new Error(
            `Argon2 iterations must be between ${ARGON2_ITERATIONS.min} and ${ARGON2_ITERATIONS.max}`,
          );
        }

        if (!ARGON2_MEMORY.inRange(kdfConfig.memory)) {
          throw new Error(
            `Argon2 memory must be between ${ARGON2_MEMORY.min}mb and ${ARGON2_MEMORY.max}mb`,
          );
        }

        if (!ARGON2_PARALLELISM.inRange(kdfConfig.parallelism)) {
          throw new Error(
            `Argon2 parallelism must be between ${ARGON2_PARALLELISM.min} and ${ARGON2_PARALLELISM.max}.`,
          );
        }
        break;
    }
  }

  protected async clearAllStoredUserKeys(userId?: UserId): Promise<void> {
    await this.stateService.setUserKeyAutoUnlock(null, { userId: userId });
    await this.stateService.setPinKeyEncryptedUserKeyEphemeral(null, { userId: userId });
  }

  private async stretchKey(key: SymmetricCryptoKey): Promise<SymmetricCryptoKey> {
    const newKey = new Uint8Array(64);
    const encKey = await this.cryptoFunctionService.hkdfExpand(key.key, "enc", 32, "sha256");
    const macKey = await this.cryptoFunctionService.hkdfExpand(key.key, "mac", 32, "sha256");
    newKey.set(new Uint8Array(encKey));
    newKey.set(new Uint8Array(macKey), 32);
    return new SymmetricCryptoKey(newKey);
  }

  private async hashPhrase(hash: Uint8Array, minimumEntropy = 64) {
    const entropyPerWord = Math.log(EFFLongWordList.length) / Math.log(2);
    let numWords = Math.ceil(minimumEntropy / entropyPerWord);

    const hashArr = Array.from(new Uint8Array(hash));
    const entropyAvailable = hashArr.length * 4;
    if (numWords * entropyPerWord > entropyAvailable) {
      throw new Error("Output entropy of hash function is too small");
    }

    const phrase: string[] = [];
    let hashNumber = bigInt.fromArray(hashArr, 256);
    while (numWords--) {
      const remainder = hashNumber.mod(EFFLongWordList.length);
      hashNumber = hashNumber.divide(EFFLongWordList.length);
      phrase.push(EFFLongWordList[remainder as any]);
    }
    return phrase;
  }

  private async buildProtectedSymmetricKey<T extends SymmetricCryptoKey>(
    encryptionKey: SymmetricCryptoKey,
    newSymKey: Uint8Array,
  ): Promise<[T, EncString]> {
    let protectedSymKey: EncString = null;
    if (encryptionKey.key.byteLength === 32) {
      const stretchedEncryptionKey = await this.stretchKey(encryptionKey);
      protectedSymKey = await this.encryptService.encrypt(newSymKey, stretchedEncryptionKey);
    } else if (encryptionKey.key.byteLength === 64) {
      protectedSymKey = await this.encryptService.encrypt(newSymKey, encryptionKey);
    } else {
      throw new Error("Invalid key size.");
    }
    return [new SymmetricCryptoKey(newSymKey) as T, protectedSymKey];
  }

  private async makeKey(
    password: string,
    salt: string,
    kdf: KdfType,
    kdfConfig: KdfConfig,
  ): Promise<SymmetricCryptoKey> {
    let key: Uint8Array = null;
    if (kdf == null || kdf === KdfType.PBKDF2_SHA256) {
      if (kdfConfig.iterations == null) {
        kdfConfig.iterations = PBKDF2_ITERATIONS.defaultValue;
      }

      key = await this.cryptoFunctionService.pbkdf2(password, salt, "sha256", kdfConfig.iterations);
    } else if (kdf == KdfType.Argon2id) {
      if (kdfConfig.iterations == null) {
        kdfConfig.iterations = ARGON2_ITERATIONS.defaultValue;
      }

      if (kdfConfig.memory == null) {
        kdfConfig.memory = ARGON2_MEMORY.defaultValue;
      }

      if (kdfConfig.parallelism == null) {
        kdfConfig.parallelism = ARGON2_PARALLELISM.defaultValue;
      }

      const saltHash = await this.cryptoFunctionService.hash(salt, "sha256");
      key = await this.cryptoFunctionService.argon2(
        password,
        saltHash,
        kdfConfig.iterations,
        kdfConfig.memory * 1024, // convert to KiB from MiB
        kdfConfig.parallelism,
      );
    } else {
      throw new Error("Unknown Kdf.");
    }
    return new SymmetricCryptoKey(key);
  }

  // --LEGACY METHODS--
  // We previously used the master key for additional keys, but now we use the user key.
  // These methods support migrating the old keys to the new ones.
  // TODO: Remove after 2023.10 release (https://bitwarden.atlassian.net/browse/PM-3475)

  async clearDeprecatedKeys(keySuffix: KeySuffixOptions, userId?: UserId) {
    if (keySuffix === KeySuffixOptions.Auto) {
      await this.stateService.setCryptoMasterKeyAuto(null, { userId: userId });
    } else if (keySuffix === KeySuffixOptions.Pin) {
      await this.stateService.setEncryptedPinProtected(null, { userId: userId });
      await this.stateService.setDecryptedPinProtected(null, { userId: userId });
    }
  }

  async migrateAutoKeyIfNeeded(userId?: UserId) {
    const oldAutoKey = await this.stateService.getCryptoMasterKeyAuto({ userId: userId });
    if (!oldAutoKey) {
      return;
    }
    // Decrypt
    const masterKey = new SymmetricCryptoKey(Utils.fromB64ToArray(oldAutoKey)) as MasterKey;
    if (await this.isLegacyUser(masterKey, userId)) {
      // Legacy users don't have a user key, so no need to migrate.
      // Instead, set the master key for additional isLegacyUser checks that will log the user out.
      await this.setMasterKey(masterKey, userId);
      return;
    }
    const encryptedUserKey = await this.stateService.getEncryptedCryptoSymmetricKey({
      userId: userId,
    });
    const userKey = await this.decryptUserKeyWithMasterKey(
      masterKey,
      new EncString(encryptedUserKey),
      userId,
    );
    // Migrate
    await this.stateService.setUserKeyAutoUnlock(userKey.keyB64, { userId: userId });
    await this.stateService.setCryptoMasterKeyAuto(null, { userId: userId });
    // Set encrypted user key in case user immediately locks without syncing
    await this.setMasterKeyEncryptedUserKey(encryptedUserKey);
  }

  async decryptAndMigrateOldPinKey(
    masterPasswordOnRestart: boolean,
    pin: string,
    email: string,
    kdf: KdfType,
    kdfConfig: KdfConfig,
    oldPinKey: EncString,
  ): Promise<UserKey> {
    // Decrypt
    const masterKey = await this.decryptMasterKeyWithPin(pin, email, kdf, kdfConfig, oldPinKey);
    const encUserKey = await this.stateService.getEncryptedCryptoSymmetricKey();
    const userKey = await this.decryptUserKeyWithMasterKey(masterKey, new EncString(encUserKey));
    // Migrate
    const pinKey = await this.makePinKey(pin, email, kdf, kdfConfig);
    const pinProtectedKey = await this.encryptService.encrypt(userKey.key, pinKey);
    if (masterPasswordOnRestart) {
      await this.stateService.setDecryptedPinProtected(null);
      await this.stateService.setPinKeyEncryptedUserKeyEphemeral(pinProtectedKey);
    } else {
      await this.stateService.setEncryptedPinProtected(null);
      await this.stateService.setPinKeyEncryptedUserKey(pinProtectedKey);
      // We previously only set the protected pin if MP on Restart was enabled
      // now we set it regardless
      const encPin = await this.encryptService.encrypt(pin, userKey);
      await this.stateService.setProtectedPin(encPin.encryptedString);
    }
    // This also clears the old Biometrics key since the new Biometrics key will
    // be created when the user key is set.
    await this.stateService.setCryptoMasterKeyBiometric(null);
    return userKey;
  }

  // --DEPRECATED METHODS--

  /**
   * @deprecated July 25 2022: Get the key you need from CryptoService (getKeyForUserEncryption or getOrgKey)
   * and then call encryptService.encrypt
   */
  async encrypt(plainValue: string | Uint8Array, key?: SymmetricCryptoKey): Promise<EncString> {
    key ||= await this.getUserKeyWithLegacySupport();
    return await this.encryptService.encrypt(plainValue, key);
  }

  /**
   * @deprecated July 25 2022: Get the key you need from CryptoService (getKeyForUserEncryption or getOrgKey)
   * and then call encryptService.encryptToBytes
   */
  async encryptToBytes(plainValue: Uint8Array, key?: SymmetricCryptoKey): Promise<EncArrayBuffer> {
    key ||= await this.getUserKeyWithLegacySupport();
    return this.encryptService.encryptToBytes(plainValue, key);
  }

  /**
   * @deprecated July 25 2022: Get the key you need from CryptoService (getKeyForUserEncryption or getOrgKey)
   * and then call encryptService.decryptToBytes
   */
  async decryptToBytes(encString: EncString, key?: SymmetricCryptoKey): Promise<Uint8Array> {
    key ||= await this.getUserKeyWithLegacySupport();
    return this.encryptService.decryptToBytes(encString, key);
  }

  /**
   * @deprecated July 25 2022: Get the key you need from CryptoService (getKeyForUserEncryption or getOrgKey)
   * and then call encryptService.decryptToUtf8
   */
  async decryptToUtf8(encString: EncString, key?: SymmetricCryptoKey): Promise<string> {
    key ||= await this.getUserKeyWithLegacySupport();
    return await this.encryptService.decryptToUtf8(encString, key);
  }

  /**
   * @deprecated July 25 2022: Get the key you need from CryptoService (getKeyForUserEncryption or getOrgKey)
   * and then call encryptService.decryptToBytes
   */
  async decryptFromBytes(encBuffer: EncArrayBuffer, key: SymmetricCryptoKey): Promise<Uint8Array> {
    if (encBuffer == null) {
      throw new Error("No buffer provided for decryption.");
    }

    key ||= await this.getUserKeyWithLegacySupport();

    return this.encryptService.decryptToBytes(encBuffer, key);
  }
}