/*
Copyright 2022-2023 The Matrix.org Foundation C.I.C.

Licensed under the Apache License, Version 2.0 (the "License");
you may not use this file except in compliance with the License.
You may obtain a copy of the License at

    http://www.apache.org/licenses/LICENSE-2.0

Unless required by applicable law or agreed to in writing, software
distributed under the License is distributed on an "AS IS" BASIS,
WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
See the License for the specific language governing permissions and
limitations under the License.
*/

import anotherjson from "another-json";
import * as RustSdkCryptoJs from "@matrix-org/matrix-sdk-crypto-wasm";

import type { IEventDecryptionResult, IMegolmSessionData } from "../@types/crypto";
import type { IDeviceLists, IToDeviceEvent } from "../sync-accumulator";
import type { IEncryptedEventInfo } from "../crypto/api";
import { IContent, MatrixEvent, MatrixEventEvent } from "../models/event";
import { Room } from "../models/room";
import { RoomMember } from "../models/room-member";
import { BackupDecryptor, CryptoBackend, OnSyncCompletedData } from "../common-crypto/CryptoBackend";
import { Logger } from "../logger";
import { IHttpOpts, MatrixHttpApi, Method } from "../http-api";
import { RoomEncryptor } from "./RoomEncryptor";
import { OutgoingRequestProcessor } from "./OutgoingRequestProcessor";
import { KeyClaimManager } from "./KeyClaimManager";
import { MapWithDefault } from "../utils";
import {
    BackupTrustInfo,
    BootstrapCrossSigningOpts,
    CreateSecretStorageOpts,
    CrossSigningKey,
    CrossSigningKeyInfo,
    CrossSigningStatus,
    CryptoCallbacks,
    Curve25519AuthData,
    DeviceVerificationStatus,
    EventEncryptionInfo,
    EventShieldColour,
    EventShieldReason,
    GeneratedSecretStorageKey,
    ImportRoomKeysOpts,
    KeyBackupCheck,
    KeyBackupInfo,
    OwnDeviceKeys,
    UserVerificationStatus,
    VerificationRequest,
} from "../crypto-api";
import { deviceKeysToDeviceMap, rustDeviceToJsDevice } from "./device-converter";
import { IDownloadKeyResult, IQueryKeysRequest } from "../client";
import { Device, DeviceMap } from "../models/device";
import { AddSecretStorageKeyOpts, SECRET_STORAGE_ALGORITHM_V1_AES, ServerSideSecretStorage } from "../secret-storage";
import { CrossSigningIdentity } from "./CrossSigningIdentity";
import { secretStorageCanAccessSecrets, secretStorageContainsCrossSigningKeys } from "./secret-storage";
import { keyFromPassphrase } from "../crypto/key_passphrase";
import { encodeRecoveryKey } from "../crypto/recoverykey";
import { crypto } from "../crypto/crypto";
import { isVerificationEvent, RustVerificationRequest, verificationMethodIdentifierToMethod } from "./verification";
import { EventType, MsgType } from "../@types/event";
import { CryptoEvent } from "../crypto";
import { TypedEventEmitter } from "../models/typed-event-emitter";
import { RustBackupCryptoEventMap, RustBackupCryptoEvents, RustBackupManager } from "./backup";
import { TypedReEmitter } from "../ReEmitter";
import { randomString } from "../randomstring";
import { ClientStoppedError } from "../errors";
import { ISignatures } from "../@types/signed";
import { encodeBase64 } from "../base64";
import { DecryptionError } from "../crypto/algorithms";
import { OutgoingRequestsManager } from "./OutgoingRequestsManager";
import { PerSessionKeyBackupDownloader } from "./PerSessionKeyBackupDownloader";

const ALL_VERIFICATION_METHODS = ["m.sas.v1", "m.qr_code.scan.v1", "m.qr_code.show.v1", "m.reciprocate.v1"];

interface ISignableObject {
    signatures?: ISignatures;
    unsigned?: object;
}

/**
 * An implementation of {@link CryptoBackend} using the Rust matrix-sdk-crypto.
 *
 * @internal
 */
export class RustCrypto extends TypedEventEmitter<RustCryptoEvents, RustCryptoEventMap> implements CryptoBackend {
    private _trustCrossSignedDevices = true;

    /** whether {@link stop} has been called */
    private stopped = false;

    /** mapping of roomId → encryptor class */
    private roomEncryptors: Record<string, RoomEncryptor> = {};

    private eventDecryptor: EventDecryptor;
    private keyClaimManager: KeyClaimManager;
    private outgoingRequestProcessor: OutgoingRequestProcessor;
    private crossSigningIdentity: CrossSigningIdentity;
    private readonly backupManager: RustBackupManager;
    private outgoingRequestsManager: OutgoingRequestsManager;

    private readonly perSessionBackupDownloader: PerSessionKeyBackupDownloader;

    private readonly reemitter = new TypedReEmitter<RustCryptoEvents, RustCryptoEventMap>(this);

    public constructor(
        private readonly logger: Logger,

        /** The `OlmMachine` from the underlying rust crypto sdk. */
        private readonly olmMachine: RustSdkCryptoJs.OlmMachine,

        /**
         * Low-level HTTP interface: used to make outgoing requests required by the rust SDK.
         *
         * We expect it to set the access token, etc.
         */
        private readonly http: MatrixHttpApi<IHttpOpts & { onlyData: true }>,

        /** The local user's User ID. */
        private readonly userId: string,

        /** The local user's Device ID. */
        _deviceId: string,

        /** Interface to server-side secret storage */
        private readonly secretStorage: ServerSideSecretStorage,

        /** Crypto callbacks provided by the application */
        private readonly cryptoCallbacks: CryptoCallbacks,
    ) {
        super();
        this.outgoingRequestProcessor = new OutgoingRequestProcessor(olmMachine, http);
        this.outgoingRequestsManager = new OutgoingRequestsManager(
            this.logger,
            olmMachine,
            this.outgoingRequestProcessor,
        );

        this.keyClaimManager = new KeyClaimManager(olmMachine, this.outgoingRequestProcessor);

        this.backupManager = new RustBackupManager(olmMachine, http, this.outgoingRequestProcessor);

        this.perSessionBackupDownloader = new PerSessionKeyBackupDownloader(
            this.logger,
            this.olmMachine,
            this.http,
            this.backupManager,
        );

        this.eventDecryptor = new EventDecryptor(this.logger, olmMachine, this.perSessionBackupDownloader);

        this.reemitter.reEmit(this.backupManager, [
            CryptoEvent.KeyBackupStatus,
            CryptoEvent.KeyBackupSessionsRemaining,
            CryptoEvent.KeyBackupFailed,
            CryptoEvent.KeyBackupDecryptionKeyCached,
        ]);

        this.crossSigningIdentity = new CrossSigningIdentity(olmMachine, this.outgoingRequestProcessor, secretStorage);

        // Check and start in background the key backup connection
        this.checkKeyBackupAndEnable();
    }

    /**
     * Return the OlmMachine only if {@link RustCrypto#stop} has not been called.
     *
     * This allows us to better handle race conditions where the client is stopped before or during a crypto API call.
     *
     * @throws ClientStoppedError if {@link RustCrypto#stop} has been called.
     */
    private getOlmMachineOrThrow(): RustSdkCryptoJs.OlmMachine {
        if (this.stopped) {
            throw new ClientStoppedError();
        }
        return this.olmMachine;
    }

    ///////////////////////////////////////////////////////////////////////////////////////////////////////////////////
    //
    // CryptoBackend implementation
    //
    ///////////////////////////////////////////////////////////////////////////////////////////////////////////////////

    public set globalErrorOnUnknownDevices(_v: boolean) {
        // Not implemented for rust crypto.
    }

    public get globalErrorOnUnknownDevices(): boolean {
        // Not implemented for rust crypto.
        return false;
    }

    public stop(): void {
        // stop() may be called multiple times, but attempting to close() the OlmMachine twice
        // will cause an error.
        if (this.stopped) {
            return;
        }
        this.stopped = true;

        this.keyClaimManager.stop();
        this.backupManager.stop();
        this.outgoingRequestsManager.stop();
        this.perSessionBackupDownloader.stop();

        // make sure we close() the OlmMachine; doing so means that all the Rust objects will be
        // cleaned up; in particular, the indexeddb connections will be closed, which means they
        // can then be deleted.
        this.olmMachine.close();
    }

    public async encryptEvent(event: MatrixEvent, _room: Room): Promise<void> {
        const roomId = event.getRoomId()!;
        const encryptor = this.roomEncryptors[roomId];

        if (!encryptor) {
            throw new Error(`Cannot encrypt event in unconfigured room ${roomId}`);
        }

        await encryptor.encryptEvent(event, this.globalBlacklistUnverifiedDevices);
    }

    public async decryptEvent(event: MatrixEvent): Promise<IEventDecryptionResult> {
        const roomId = event.getRoomId();
        if (!roomId) {
            // presumably, a to-device message. These are normally decrypted in preprocessToDeviceMessages
            // so the fact it has come back here suggests that decryption failed.
            //
            // once we drop support for the libolm crypto implementation, we can stop passing to-device messages
            // through decryptEvent and hence get rid of this case.
            throw new Error("to-device event was not decrypted in preprocessToDeviceMessages");
        }
        return await this.eventDecryptor.attemptEventDecryption(event);
    }

    /**
     * Implementation of (deprecated) {@link MatrixClient#getEventEncryptionInfo}.
     *
     * @param event - event to inspect
     */
    public getEventEncryptionInfo(event: MatrixEvent): IEncryptedEventInfo {
        const ret: Partial<IEncryptedEventInfo> = {};

        ret.senderKey = event.getSenderKey() ?? undefined;
        ret.algorithm = event.getWireContent().algorithm;

        if (!ret.senderKey || !ret.algorithm) {
            ret.encrypted = false;
            return ret as IEncryptedEventInfo;
        }
        ret.encrypted = true;
        ret.authenticated = true;
        ret.mismatchedSender = true;
        return ret as IEncryptedEventInfo;
    }

    /**
     * Implementation of {@link CryptoBackend#checkUserTrust}.
     *
     * Stub for backwards compatibility.
     *
     */
    public checkUserTrust(userId: string): UserVerificationStatus {
        return new UserVerificationStatus(false, false, false);
    }

    /**
     * Get the cross signing information for a given user.
     *
     * The cross-signing API is currently UNSTABLE and may change without notice.
     *
     * @param userId - the user ID to get the cross-signing info for.
     *
     * @returns the cross signing information for the user.
     */
    public getStoredCrossSigningForUser(userId: string): null {
        // TODO
        return null;
    }

    /**
     * This function is unneeded for the rust-crypto.
     * The cross signing key import and the device verification are done in {@link CryptoApi#bootstrapCrossSigning}
     *
     * The function is stub to keep the compatibility with the old crypto.
     * More information: https://github.com/vector-im/element-web/issues/25648
     *
     * Implementation of {@link CryptoBackend#checkOwnCrossSigningTrust}
     */
    public async checkOwnCrossSigningTrust(): Promise<void> {
        return;
    }

    ///////////////////////////////////////////////////////////////////////////////////////////////////////////////////
    //
    // CryptoApi implementation
    //
    ///////////////////////////////////////////////////////////////////////////////////////////////////////////////////

    public globalBlacklistUnverifiedDevices = false;

    /**
     * Implementation of {@link CryptoApi#getVersion}.
     */
    public getVersion(): string {
        const versions = RustSdkCryptoJs.getVersions();
        return `Rust SDK ${versions.matrix_sdk_crypto} (${versions.git_sha}), Vodozemac ${versions.vodozemac}`;
    }

    /**
     * Implementation of {@link CryptoApi#getOwnDeviceKeys}.
     */
    public async getOwnDeviceKeys(): Promise<OwnDeviceKeys> {
        const device: RustSdkCryptoJs.Device = await this.olmMachine.getDevice(
            this.olmMachine.userId,
            this.olmMachine.deviceId,
        );
        // could be undefined if there is no such algorithm for that device.
        if (device.curve25519Key && device.ed25519Key) {
            return {
                ed25519: device.ed25519Key.toBase64(),
                curve25519: device.curve25519Key.toBase64(),
            };
        }
        throw new Error("Device keys not found");
    }

    public prepareToEncrypt(room: Room): void {
        const encryptor = this.roomEncryptors[room.roomId];

        if (encryptor) {
            encryptor.prepareForEncryption(this.globalBlacklistUnverifiedDevices);
        }
    }

    public forceDiscardSession(roomId: string): Promise<void> {
        return this.roomEncryptors[roomId]?.forceDiscardSession();
    }

    public async exportRoomKeys(): Promise<IMegolmSessionData[]> {
        const raw = await this.olmMachine.exportRoomKeys(() => true);
        return JSON.parse(raw);
    }

    public async importRoomKeys(keys: IMegolmSessionData[], opts?: ImportRoomKeysOpts): Promise<void> {
        return await this.backupManager.importRoomKeys(keys, opts);
    }

    /**
     * Implementation of {@link CryptoApi.userHasCrossSigningKeys}.
     */
    public async userHasCrossSigningKeys(userId = this.userId, downloadUncached = false): Promise<boolean> {
        // TODO: could probably do with a more efficient way of doing this than returning the whole set and searching
        const rustTrackedUsers: Set<RustSdkCryptoJs.UserId> = await this.olmMachine.trackedUsers();
        let rustTrackedUser: RustSdkCryptoJs.UserId | undefined;
        for (const u of rustTrackedUsers) {
            if (userId === u.toString()) {
                rustTrackedUser = u;
                break;
            }
        }

        if (rustTrackedUser !== undefined) {
            if (userId === this.userId) {
                /* make sure we have an *up-to-date* idea of the user's cross-signing keys. This is important, because if we
                 * return "false" here, we will end up generating new cross-signing keys and replacing the existing ones.
                 */
                const request = this.olmMachine.queryKeysForUsers([rustTrackedUser]);
                await this.outgoingRequestProcessor.makeOutgoingRequest(request);
            }
            const userIdentity = await this.olmMachine.getIdentity(rustTrackedUser);
            userIdentity?.free();
            return userIdentity !== undefined;
        } else if (downloadUncached) {
            // Download the cross signing keys and check if the master key is available
            const keyResult = await this.downloadDeviceList(new Set([userId]));
            const keys = keyResult.master_keys?.[userId];

            // No master key
            if (!keys) return false;

            // `keys` is an object with { [`ed25519:${pubKey}`]: pubKey }
            // We assume only a single key, and we want the bare form without type
            // prefix, so we select the values.
            return Boolean(Object.values(keys.keys)[0]);
        } else {
            return false;
        }
    }

    /**
     * Get the device information for the given list of users.
     *
     * @param userIds - The users to fetch.
     * @param downloadUncached - If true, download the device list for users whose device list we are not
     *    currently tracking. Defaults to false, in which case such users will not appear at all in the result map.
     *
     * @returns A map `{@link DeviceMap}`.
     */
    public async getUserDeviceInfo(userIds: string[], downloadUncached = false): Promise<DeviceMap> {
        const deviceMapByUserId = new Map<string, Map<string, Device>>();
        const rustTrackedUsers: Set<RustSdkCryptoJs.UserId> = await this.getOlmMachineOrThrow().trackedUsers();

        // Convert RustSdkCryptoJs.UserId to a `Set<string>`
        const trackedUsers = new Set<string>();
        rustTrackedUsers.forEach((rustUserId) => trackedUsers.add(rustUserId.toString()));

        // Keep untracked user to download their keys after
        const untrackedUsers: Set<string> = new Set();

        for (const userId of userIds) {
            // if this is a tracked user, we can just fetch the device list from the rust-sdk
            // (NB: this is probably ok even if we race with a leave event such that we stop tracking the user's
            // devices: the rust-sdk will return the last-known device list, which will be good enough.)
            if (trackedUsers.has(userId)) {
                deviceMapByUserId.set(userId, await this.getUserDevices(userId));
            } else {
                untrackedUsers.add(userId);
            }
        }

        // for any users whose device lists we are not tracking, fall back to downloading the device list
        // over HTTP.
        if (downloadUncached && untrackedUsers.size >= 1) {
            const queryResult = await this.downloadDeviceList(untrackedUsers);
            Object.entries(queryResult.device_keys).forEach(([userId, deviceKeys]) =>
                deviceMapByUserId.set(userId, deviceKeysToDeviceMap(deviceKeys)),
            );
        }

        return deviceMapByUserId;
    }

    /**
     * Get the device list for the given user from the olm machine
     * @param userId - Rust SDK UserId
     */
    private async getUserDevices(userId: string): Promise<Map<string, Device>> {
        const rustUserId = new RustSdkCryptoJs.UserId(userId);

        // For reasons I don't really understand, the Javascript FinalizationRegistry doesn't seem to run the
        // registered callbacks when `userDevices` goes out of scope, nor when the individual devices in the array
        // returned by `userDevices.devices` do so.
        //
        // This is particularly problematic, because each of those structures holds a reference to the
        // VerificationMachine, which in turn holds a reference to the IndexeddbCryptoStore. Hence, we end up leaking
        // open connections to the crypto store, which means the store can't be deleted on logout.
        //
        // To fix this, we explicitly call `.free` on each of the objects, which tells the rust code to drop the
        // allocated memory and decrement the refcounts for the crypto store.

        // Wait for up to a second for any in-flight device list requests to complete.
        // The reason for this isn't so much to avoid races (some level of raciness is
        // inevitable for this method) but to make testing easier.
        const userDevices: RustSdkCryptoJs.UserDevices = await this.olmMachine.getUserDevices(rustUserId, 1);
        try {
            const deviceArray: RustSdkCryptoJs.Device[] = userDevices.devices();
            try {
                return new Map(
                    deviceArray.map((device) => [device.deviceId.toString(), rustDeviceToJsDevice(device, rustUserId)]),
                );
            } finally {
                deviceArray.forEach((d) => d.free());
            }
        } finally {
            userDevices.free();
        }
    }

    /**
     * Download the given user keys by calling `/keys/query` request
     * @param untrackedUsers - download keys of these users
     */
    private async downloadDeviceList(untrackedUsers: Set<string>): Promise<IDownloadKeyResult> {
        const queryBody: IQueryKeysRequest = { device_keys: {} };
        untrackedUsers.forEach((user) => (queryBody.device_keys[user] = []));

        return await this.http.authedRequest(Method.Post, "/_matrix/client/v3/keys/query", undefined, queryBody, {
            prefix: "",
        });
    }

    /**
     * Implementation of {@link CryptoApi#getTrustCrossSignedDevices}.
     */
    public getTrustCrossSignedDevices(): boolean {
        return this._trustCrossSignedDevices;
    }

    /**
     * Implementation of {@link CryptoApi#setTrustCrossSignedDevices}.
     */
    public setTrustCrossSignedDevices(val: boolean): void {
        this._trustCrossSignedDevices = val;
        // TODO: legacy crypto goes through the list of known devices and emits DeviceVerificationChanged
        //  events. Maybe we need to do the same?
    }

    /**
     * Mark the given device as locally verified.
     *
     * Implementation of {@link CryptoApi#setDeviceVerified}.
     */
    public async setDeviceVerified(userId: string, deviceId: string, verified = true): Promise<void> {
        const device: RustSdkCryptoJs.Device | undefined = await this.olmMachine.getDevice(
            new RustSdkCryptoJs.UserId(userId),
            new RustSdkCryptoJs.DeviceId(deviceId),
        );

        if (!device) {
            throw new Error(`Unknown device ${userId}|${deviceId}`);
        }
        try {
            await device.setLocalTrust(
                verified ? RustSdkCryptoJs.LocalTrust.Verified : RustSdkCryptoJs.LocalTrust.Unset,
            );
        } finally {
            device.free();
        }
    }

    /**
     * Blindly cross-sign one of our other devices.
     *
     * Implementation of {@link CryptoApi#crossSignDevice}.
     */
    public async crossSignDevice(deviceId: string): Promise<void> {
        const device: RustSdkCryptoJs.Device | undefined = await this.olmMachine.getDevice(
            new RustSdkCryptoJs.UserId(this.userId),
            new RustSdkCryptoJs.DeviceId(deviceId),
        );
        if (!device) {
            throw new Error(`Unknown device ${deviceId}`);
        }
        try {
            const outgoingRequest: RustSdkCryptoJs.SignatureUploadRequest = await device.verify();
            await this.outgoingRequestProcessor.makeOutgoingRequest(outgoingRequest);
        } finally {
            device.free();
        }
    }

    /**
     * Implementation of {@link CryptoApi#getDeviceVerificationStatus}.
     */
    public async getDeviceVerificationStatus(
        userId: string,
        deviceId: string,
    ): Promise<DeviceVerificationStatus | null> {
        const device: RustSdkCryptoJs.Device | undefined = await this.olmMachine.getDevice(
            new RustSdkCryptoJs.UserId(userId),
            new RustSdkCryptoJs.DeviceId(deviceId),
        );

        if (!device) return null;
        try {
            return new DeviceVerificationStatus({
                signedByOwner: device.isCrossSignedByOwner(),
                crossSigningVerified: device.isCrossSigningTrusted(),
                localVerified: device.isLocallyTrusted(),
                trustCrossSignedDevices: this._trustCrossSignedDevices,
            });
        } finally {
            device.free();
        }
    }

    /**
     * Implementation of {@link CryptoApi#getUserVerificationStatus}.
     */
    public async getUserVerificationStatus(userId: string): Promise<UserVerificationStatus> {
        const userIdentity: RustSdkCryptoJs.UserIdentity | RustSdkCryptoJs.OwnUserIdentity | undefined =
            await this.getOlmMachineOrThrow().getIdentity(new RustSdkCryptoJs.UserId(userId));
        if (userIdentity === undefined) {
            return new UserVerificationStatus(false, false, false);
        }
        const verified = userIdentity.isVerified();
        userIdentity.free();
        return new UserVerificationStatus(verified, false, false);
    }

    /**
     * Implementation of {@link CryptoApi#isCrossSigningReady}
     */
    public async isCrossSigningReady(): Promise<boolean> {
        const { publicKeysOnDevice, privateKeysInSecretStorage, privateKeysCachedLocally } =
            await this.getCrossSigningStatus();
        const hasKeysInCache =
            Boolean(privateKeysCachedLocally.masterKey) &&
            Boolean(privateKeysCachedLocally.selfSigningKey) &&
            Boolean(privateKeysCachedLocally.userSigningKey);

        // The cross signing is ready if the public and private keys are available
        return publicKeysOnDevice && (hasKeysInCache || privateKeysInSecretStorage);
    }

    /**
     * Implementation of {@link CryptoApi#getCrossSigningKeyId}
     */
    public async getCrossSigningKeyId(type: CrossSigningKey = CrossSigningKey.Master): Promise<string | null> {
        const userIdentity: RustSdkCryptoJs.OwnUserIdentity | undefined = await this.olmMachine.getIdentity(
            new RustSdkCryptoJs.UserId(this.userId),
        );
        if (!userIdentity) {
            // The public keys are not available on this device
            return null;
        }

        try {
            const crossSigningStatus: RustSdkCryptoJs.CrossSigningStatus = await this.olmMachine.crossSigningStatus();

            const privateKeysOnDevice =
                crossSigningStatus.hasMaster && crossSigningStatus.hasUserSigning && crossSigningStatus.hasSelfSigning;

            if (!privateKeysOnDevice) {
                // The private keys are not available on this device
                return null;
            }

            if (!userIdentity.isVerified()) {
                // We have both public and private keys, but they don't match!
                return null;
            }

            let key: string;
            switch (type) {
                case CrossSigningKey.Master:
                    key = userIdentity.masterKey;
                    break;
                case CrossSigningKey.SelfSigning:
                    key = userIdentity.selfSigningKey;
                    break;
                case CrossSigningKey.UserSigning:
                    key = userIdentity.userSigningKey;
                    break;
                default:
                    // Unknown type
                    return null;
            }

            const parsedKey: CrossSigningKeyInfo = JSON.parse(key);
            // `keys` is an object with { [`ed25519:${pubKey}`]: pubKey }
            // We assume only a single key, and we want the bare form without type
            // prefix, so we select the values.
            return Object.values(parsedKey.keys)[0];
        } finally {
            userIdentity.free();
        }
    }

    /**
     * Implementation of {@link CryptoApi#boostrapCrossSigning}
     */
    public async bootstrapCrossSigning(opts: BootstrapCrossSigningOpts): Promise<void> {
        await this.crossSigningIdentity.bootstrapCrossSigning(opts);
    }

    /**
     * Implementation of {@link CryptoApi#isSecretStorageReady}
     */
    public async isSecretStorageReady(): Promise<boolean> {
        // make sure that the cross-signing keys are stored
        const secretsToCheck = [
            "m.cross_signing.master",
            "m.cross_signing.user_signing",
            "m.cross_signing.self_signing",
        ];

        // if key backup is active, we also need to check that the backup decryption key is stored
        const keyBackupEnabled = (await this.backupManager.getActiveBackupVersion()) != null;
        if (keyBackupEnabled) {
            secretsToCheck.push("m.megolm_backup.v1");
        }

        return secretStorageCanAccessSecrets(this.secretStorage, secretsToCheck);
    }

    /**
     * Implementation of {@link CryptoApi#bootstrapSecretStorage}
     */
    public async bootstrapSecretStorage({
        createSecretStorageKey,
        setupNewSecretStorage,
        setupNewKeyBackup,
    }: CreateSecretStorageOpts = {}): Promise<void> {
        // If an AES Key is already stored in the secret storage and setupNewSecretStorage is not set
        // we don't want to create a new key
        const isNewSecretStorageKeyNeeded = setupNewSecretStorage || !(await this.secretStorageHasAESKey());

        if (isNewSecretStorageKeyNeeded) {
            if (!createSecretStorageKey) {
                throw new Error("unable to create a new secret storage key, createSecretStorageKey is not set");
            }

            // Create a new storage key and add it to secret storage
            this.logger.info("bootstrapSecretStorage: creating new secret storage key");
            const recoveryKey = await createSecretStorageKey();
            await this.addSecretStorageKeyToSecretStorage(recoveryKey);
        }

        const crossSigningStatus: RustSdkCryptoJs.CrossSigningStatus = await this.olmMachine.crossSigningStatus();
        const hasPrivateKeys =
            crossSigningStatus.hasMaster && crossSigningStatus.hasSelfSigning && crossSigningStatus.hasUserSigning;

        // If we have cross-signing private keys cached, store them in secret
        // storage if they are not there already.
        if (
            hasPrivateKeys &&
            (isNewSecretStorageKeyNeeded || !(await secretStorageContainsCrossSigningKeys(this.secretStorage)))
        ) {
            this.logger.info("bootstrapSecretStorage: cross-signing keys not yet exported; doing so now.");

            const crossSigningPrivateKeys: RustSdkCryptoJs.CrossSigningKeyExport =
                await this.olmMachine.exportCrossSigningKeys();

            if (!crossSigningPrivateKeys.masterKey) {
                throw new Error("missing master key in cross signing private keys");
            }

            if (!crossSigningPrivateKeys.userSigningKey) {
                throw new Error("missing user signing key in cross signing private keys");
            }

            if (!crossSigningPrivateKeys.self_signing_key) {
                throw new Error("missing self signing key in cross signing private keys");
            }

            await this.secretStorage.store("m.cross_signing.master", crossSigningPrivateKeys.masterKey);
            await this.secretStorage.store("m.cross_signing.user_signing", crossSigningPrivateKeys.userSigningKey);
            await this.secretStorage.store("m.cross_signing.self_signing", crossSigningPrivateKeys.self_signing_key);

            if (setupNewKeyBackup) {
                await this.resetKeyBackup();
            }
        }
    }

    /**
     * Add the secretStorage key to the secret storage
     * - The secret storage key must have the `keyInfo` field filled
     * - The secret storage key is set as the default key of the secret storage
     * - Call `cryptoCallbacks.cacheSecretStorageKey` when done
     *
     * @param secretStorageKey - The secret storage key to add in the secret storage.
     */
    private async addSecretStorageKeyToSecretStorage(secretStorageKey: GeneratedSecretStorageKey): Promise<void> {
        // keyInfo is required to continue
        if (!secretStorageKey.keyInfo) {
            throw new Error("missing keyInfo field in the secret storage key");
        }

        const secretStorageKeyObject = await this.secretStorage.addKey(
            SECRET_STORAGE_ALGORITHM_V1_AES,
            secretStorageKey.keyInfo,
        );

        await this.secretStorage.setDefaultKeyId(secretStorageKeyObject.keyId);

        this.cryptoCallbacks.cacheSecretStorageKey?.(
            secretStorageKeyObject.keyId,
            secretStorageKeyObject.keyInfo,
            secretStorageKey.privateKey,
        );
    }

    /**
     * Check if a secret storage AES Key is already added in secret storage
     *
     * @returns True if an AES key is in the secret storage
     */
    private async secretStorageHasAESKey(): Promise<boolean> {
        // See if we already have an AES secret-storage key.
        const secretStorageKeyTuple = await this.secretStorage.getKey();

        if (!secretStorageKeyTuple) return false;

        const [, keyInfo] = secretStorageKeyTuple;

        // Check if the key is an AES key
        return keyInfo.algorithm === SECRET_STORAGE_ALGORITHM_V1_AES;
    }

    /**
     * Implementation of {@link CryptoApi#getCrossSigningStatus}
     */
    public async getCrossSigningStatus(): Promise<CrossSigningStatus> {
        const userIdentity: RustSdkCryptoJs.OwnUserIdentity | null = await this.getOlmMachineOrThrow().getIdentity(
            new RustSdkCryptoJs.UserId(this.userId),
        );

        const publicKeysOnDevice =
            Boolean(userIdentity?.masterKey) &&
            Boolean(userIdentity?.selfSigningKey) &&
            Boolean(userIdentity?.userSigningKey);
        userIdentity?.free();

        const privateKeysInSecretStorage = await secretStorageContainsCrossSigningKeys(this.secretStorage);
        const crossSigningStatus: RustSdkCryptoJs.CrossSigningStatus | null =
            await this.getOlmMachineOrThrow().crossSigningStatus();

        return {
            publicKeysOnDevice,
            privateKeysInSecretStorage,
            privateKeysCachedLocally: {
                masterKey: Boolean(crossSigningStatus?.hasMaster),
                userSigningKey: Boolean(crossSigningStatus?.hasUserSigning),
                selfSigningKey: Boolean(crossSigningStatus?.hasSelfSigning),
            },
        };
    }

    /**
     * Implementation of {@link CryptoApi#createRecoveryKeyFromPassphrase}
     */
    public async createRecoveryKeyFromPassphrase(password?: string): Promise<GeneratedSecretStorageKey> {
        let key: Uint8Array;

        const keyInfo: AddSecretStorageKeyOpts = {};
        if (password) {
            // Generate the key from the passphrase
            const derivation = await keyFromPassphrase(password);
            keyInfo.passphrase = {
                algorithm: "m.pbkdf2",
                iterations: derivation.iterations,
                salt: derivation.salt,
            };
            key = derivation.key;
        } else {
            // Using the navigator crypto API to generate the private key
            key = new Uint8Array(32);
            crypto.getRandomValues(key);
        }

        const encodedPrivateKey = encodeRecoveryKey(key);
        return {
            keyInfo,
            encodedPrivateKey,
            privateKey: key,
        };
    }

    /**
     * Implementation of {@link CryptoApi.getEncryptionInfoForEvent}.
     */
    public async getEncryptionInfoForEvent(event: MatrixEvent): Promise<EventEncryptionInfo | null> {
        return this.eventDecryptor.getEncryptionInfoForEvent(event);
    }

    /**
     * Returns to-device verification requests that are already in progress for the given user id.
     *
     * Implementation of {@link CryptoApi#getVerificationRequestsToDeviceInProgress}
     *
     * @param userId - the ID of the user to query
     *
     * @returns the VerificationRequests that are in progress
     */
    public getVerificationRequestsToDeviceInProgress(userId: string): VerificationRequest[] {
        const requests: RustSdkCryptoJs.VerificationRequest[] = this.olmMachine.getVerificationRequests(
            new RustSdkCryptoJs.UserId(userId),
        );
        return requests
            .filter((request) => request.roomId === undefined)
            .map(
                (request) =>
                    new RustVerificationRequest(
                        this.olmMachine,
                        request,
                        this.outgoingRequestProcessor,
                        this._supportedVerificationMethods,
                    ),
            );
    }

    /**
     * Finds a DM verification request that is already in progress for the given room id
     *
     * Implementation of {@link CryptoApi#findVerificationRequestDMInProgress}
     *
     * @param roomId - the room to use for verification
     * @param userId - search the verification request for the given user
     *
     * @returns the VerificationRequest that is in progress, if any
     *
     */
    public findVerificationRequestDMInProgress(roomId: string, userId?: string): VerificationRequest | undefined {
        if (!userId) throw new Error("missing userId");

        const requests: RustSdkCryptoJs.VerificationRequest[] = this.olmMachine.getVerificationRequests(
            new RustSdkCryptoJs.UserId(userId),
        );

        // Search for the verification request for the given room id
        const request = requests.find((request) => request.roomId?.toString() === roomId);

        if (request) {
            return new RustVerificationRequest(
                this.olmMachine,
                request,
                this.outgoingRequestProcessor,
                this._supportedVerificationMethods,
            );
        }
    }

    /**
     * Implementation of {@link CryptoApi#requestVerificationDM}
     */
    public async requestVerificationDM(userId: string, roomId: string): Promise<VerificationRequest> {
        const userIdentity: RustSdkCryptoJs.UserIdentity | undefined = await this.olmMachine.getIdentity(
            new RustSdkCryptoJs.UserId(userId),
        );

        if (!userIdentity) throw new Error(`unknown userId ${userId}`);

        try {
            // Transform the verification methods into rust objects
            const methods = this._supportedVerificationMethods.map((method) =>
                verificationMethodIdentifierToMethod(method),
            );
            // Get the request content to send to the DM room
            const verificationEventContent: string = await userIdentity.verificationRequestContent(methods);

            // Send the request content to send to the DM room
            const eventId = await this.sendVerificationRequestContent(roomId, verificationEventContent);

            // Get a verification request
            const request: RustSdkCryptoJs.VerificationRequest = await userIdentity.requestVerification(
                new RustSdkCryptoJs.RoomId(roomId),
                new RustSdkCryptoJs.EventId(eventId),
                methods,
            );
            return new RustVerificationRequest(
                this.olmMachine,
                request,
                this.outgoingRequestProcessor,
                this._supportedVerificationMethods,
            );
        } finally {
            userIdentity.free();
        }
    }

    /**
     * Send the verification content to a room
     * See https://spec.matrix.org/v1.7/client-server-api/#put_matrixclientv3roomsroomidsendeventtypetxnid
     *
     * Prefer to use {@link OutgoingRequestProcessor.makeOutgoingRequest} when dealing with {@link RustSdkCryptoJs.RoomMessageRequest}
     *
     * @param roomId - the targeted room
     * @param verificationEventContent - the request body.
     *
     * @returns the event id
     */
    private async sendVerificationRequestContent(roomId: string, verificationEventContent: string): Promise<string> {
        const txId = randomString(32);
        // Send the verification request content to the DM room
        const { event_id: eventId } = await this.http.authedRequest<{ event_id: string }>(
            Method.Put,
            `/_matrix/client/v3/rooms/${encodeURIComponent(roomId)}/send/m.room.message/${encodeURIComponent(txId)}`,
            undefined,
            verificationEventContent,
            {
                prefix: "",
            },
        );

        return eventId;
    }

    /**
     * The verification methods we offer to the other side during an interactive verification.
     */
    private _supportedVerificationMethods: string[] = ALL_VERIFICATION_METHODS;

    /**
     * Set the verification methods we offer to the other side during an interactive verification.
     *
     * If `undefined`, we will offer all the methods supported by the Rust SDK.
     */
    public setSupportedVerificationMethods(methods: string[] | undefined): void {
        // by default, the Rust SDK does not offer `m.qr_code.scan.v1`, but we do want to offer that.
        this._supportedVerificationMethods = methods ?? ALL_VERIFICATION_METHODS;
    }

    /**
     * Send a verification request to our other devices.
     *
     * If a verification is already in flight, returns it. Otherwise, initiates a new one.
     *
     * Implementation of {@link CryptoApi#requestOwnUserVerification}.
     *
     * @returns a VerificationRequest when the request has been sent to the other party.
     */
    public async requestOwnUserVerification(): Promise<VerificationRequest> {
        const userIdentity: RustSdkCryptoJs.OwnUserIdentity | undefined = await this.olmMachine.getIdentity(
            new RustSdkCryptoJs.UserId(this.userId),
        );
        if (userIdentity === undefined) {
            throw new Error("cannot request verification for this device when there is no existing cross-signing key");
        }

        try {
            const [request, outgoingRequest]: [RustSdkCryptoJs.VerificationRequest, RustSdkCryptoJs.ToDeviceRequest] =
                await userIdentity.requestVerification(
                    this._supportedVerificationMethods.map(verificationMethodIdentifierToMethod),
                );
            await this.outgoingRequestProcessor.makeOutgoingRequest(outgoingRequest);
            return new RustVerificationRequest(
                this.olmMachine,
                request,
                this.outgoingRequestProcessor,
                this._supportedVerificationMethods,
            );
        } finally {
            userIdentity.free();
        }
    }

    /**
     * Request an interactive verification with the given device.
     *
     * If a verification is already in flight, returns it. Otherwise, initiates a new one.
     *
     * Implementation of {@link CryptoApi#requestDeviceVerification}.
     *
     * @param userId - ID of the owner of the device to verify
     * @param deviceId - ID of the device to verify
     *
     * @returns a VerificationRequest when the request has been sent to the other party.
     */
    public async requestDeviceVerification(userId: string, deviceId: string): Promise<VerificationRequest> {
        const device: RustSdkCryptoJs.Device | undefined = await this.olmMachine.getDevice(
            new RustSdkCryptoJs.UserId(userId),
            new RustSdkCryptoJs.DeviceId(deviceId),
        );

        if (!device) {
            throw new Error("Not a known device");
        }

        try {
            const [request, outgoingRequest]: [RustSdkCryptoJs.VerificationRequest, RustSdkCryptoJs.ToDeviceRequest] =
                await device.requestVerification(
                    this._supportedVerificationMethods.map(verificationMethodIdentifierToMethod),
                );
            await this.outgoingRequestProcessor.makeOutgoingRequest(outgoingRequest);
            return new RustVerificationRequest(
                this.olmMachine,
                request,
                this.outgoingRequestProcessor,
                this._supportedVerificationMethods,
            );
        } finally {
            device.free();
        }
    }

    /**
     * Fetch the backup decryption key we have saved in our store.
     *
     * Implementation of {@link CryptoApi#getSessionBackupPrivateKey}.
     *
     * @returns the key, if any, or null
     */
    public async getSessionBackupPrivateKey(): Promise<Uint8Array | null> {
        const backupKeys: RustSdkCryptoJs.BackupKeys = await this.olmMachine.getBackupKeys();
        if (!backupKeys.decryptionKey) return null;
        return Buffer.from(backupKeys.decryptionKey.toBase64(), "base64");
    }

    /**
     * Store the backup decryption key.
     *
     * Implementation of {@link CryptoApi#storeSessionBackupPrivateKey}.
     *
     * @param key - the backup decryption key
     * @param version - the backup version for this key.
     */
    public async storeSessionBackupPrivateKey(key: Uint8Array, version?: string): Promise<void> {
        const base64Key = encodeBase64(key);

        if (!version) {
            throw new Error("storeSessionBackupPrivateKey: version is required");
        }

        await this.backupManager.saveBackupDecryptionKey(
            RustSdkCryptoJs.BackupDecryptionKey.fromBase64(base64Key),
            version,
        );
    }

    /**
     * Get the current status of key backup.
     *
     * Implementation of {@link CryptoApi#getActiveSessionBackupVersion}.
     */
    public async getActiveSessionBackupVersion(): Promise<string | null> {
        return await this.backupManager.getActiveBackupVersion();
    }

    /**
     * Determine if a key backup can be trusted.
     *
     * Implementation of {@link Crypto.CryptoApi.isKeyBackupTrusted}.
     */
    public async isKeyBackupTrusted(info: KeyBackupInfo): Promise<BackupTrustInfo> {
        return await this.backupManager.isKeyBackupTrusted(info);
    }

    /**
     * Force a re-check of the key backup and enable/disable it as appropriate.
     *
     * Implementation of {@link Crypto.CryptoApi.checkKeyBackupAndEnable}.
     */
    public async checkKeyBackupAndEnable(): Promise<KeyBackupCheck | null> {
        return await this.backupManager.checkKeyBackupAndEnable(true);
    }

    /**
     * Implementation of {@link CryptoApi#deleteKeyBackupVersion}.
     */
    public async deleteKeyBackupVersion(version: string): Promise<void> {
        await this.backupManager.deleteKeyBackupVersion(version);
    }

    /**
     * Implementation of {@link CryptoApi#resetKeyBackup}.
     */
    public async resetKeyBackup(): Promise<void> {
        const backupInfo = await this.backupManager.setupKeyBackup((o) => this.signObject(o));

        // we want to store the private key in 4S
        // need to check if 4S is set up?
        if (await this.secretStorageHasAESKey()) {
            await this.secretStorage.store("m.megolm_backup.v1", backupInfo.decryptionKey.toBase64());
        }

        // we can check and start async
        this.checkKeyBackupAndEnable();
    }

    /**
     * Signs the given object with the current device and current identity (if available).
     * As defined in {@link https://spec.matrix.org/v1.8/appendices/#signing-json | Signing JSON}.
     *
     * @param obj - The object to sign
     */
    private async signObject<T extends ISignableObject & object>(obj: T): Promise<void> {
        const sigs = new Map(Object.entries(obj.signatures || {}));
        const unsigned = obj.unsigned;

        delete obj.signatures;
        delete obj.unsigned;

        const userSignatures = sigs.get(this.userId) || {};

        const canonalizedJson = anotherjson.stringify(obj);
        const signatures: RustSdkCryptoJs.Signatures = await this.olmMachine.sign(canonalizedJson);

        const map = JSON.parse(signatures.asJSON());

        sigs.set(this.userId, { ...userSignatures, ...map[this.userId] });

        if (unsigned !== undefined) obj.unsigned = unsigned;
        obj.signatures = Object.fromEntries(sigs.entries());
    }

    /**
     * Implementation of {@link CryptoBackend#getBackupDecryptor}.
     */
    public async getBackupDecryptor(backupInfo: KeyBackupInfo, privKey: ArrayLike<number>): Promise<BackupDecryptor> {
        if (backupInfo.algorithm != "m.megolm_backup.v1.curve25519-aes-sha2") {
            throw new Error(`getBackupDecryptor Unsupported algorithm ${backupInfo.algorithm}`);
        }

        const authData = <Curve25519AuthData>backupInfo.auth_data;

        if (!(privKey instanceof Uint8Array)) {
            throw new Error(`getBackupDecryptor expects Uint8Array`);
        }

        const backupDecryptionKey = RustSdkCryptoJs.BackupDecryptionKey.fromBase64(encodeBase64(privKey));

        if (authData.public_key != backupDecryptionKey.megolmV1PublicKey.publicKeyBase64) {
            throw new Error(`getBackupDecryptor key mismatch error`);
        }

        return this.backupManager.createBackupDecryptor(backupDecryptionKey);
    }

    /**
     * Implementation of {@link CryptoBackend#importBackedUpRoomKeys}.
     */
    public async importBackedUpRoomKeys(keys: IMegolmSessionData[], opts?: ImportRoomKeysOpts): Promise<void> {
        return await this.backupManager.importBackedUpRoomKeys(keys, opts);
    }

    ///////////////////////////////////////////////////////////////////////////////////////////////////////////////////
    //
    // SyncCryptoCallbacks implementation
    //
    ///////////////////////////////////////////////////////////////////////////////////////////////////////////////////

    /**
     * Apply sync changes to the olm machine
     * @param events - the received to-device messages
     * @param oneTimeKeysCounts - the received one time key counts
     * @param unusedFallbackKeys - the received unused fallback keys
     * @param devices - the received device list updates
     * @returns A list of preprocessed to-device messages.
     */
    private async receiveSyncChanges({
        events,
        oneTimeKeysCounts = new Map<string, number>(),
        unusedFallbackKeys,
        devices = new RustSdkCryptoJs.DeviceLists(),
    }: {
        events?: IToDeviceEvent[];
        oneTimeKeysCounts?: Map<string, number>;
        unusedFallbackKeys?: Set<string>;
        devices?: RustSdkCryptoJs.DeviceLists;
    }): Promise<IToDeviceEvent[]> {
        const result = await this.olmMachine.receiveSyncChanges(
            events ? JSON.stringify(events) : "[]",
            devices,
            oneTimeKeysCounts,
            unusedFallbackKeys,
        );

        // receiveSyncChanges returns a JSON-encoded list of decrypted to-device messages.
        return JSON.parse(result);
    }

    /** called by the sync loop to preprocess incoming to-device messages
     *
     * @param events - the received to-device messages
     * @returns A list of preprocessed to-device messages.
     */
    public async preprocessToDeviceMessages(events: IToDeviceEvent[]): Promise<IToDeviceEvent[]> {
        // send the received to-device messages into receiveSyncChanges. We have no info on device-list changes,
        // one-time-keys, or fallback keys, so just pass empty data.
        const processed = await this.receiveSyncChanges({ events });

        // look for interesting to-device messages
        for (const message of processed) {
            if (message.type === EventType.KeyVerificationRequest) {
                this.onIncomingKeyVerificationRequest(message.sender, message.content);
            }
        }
        return processed;
    }

    /** called by the sync loop to process one time key counts and unused fallback keys
     *
     * @param oneTimeKeysCounts - the received one time key counts
     * @param unusedFallbackKeys - the received unused fallback keys
     */
    public async processKeyCounts(
        oneTimeKeysCounts?: Record<string, number>,
        unusedFallbackKeys?: string[],
    ): Promise<void> {
        const mapOneTimeKeysCount = oneTimeKeysCounts && new Map<string, number>(Object.entries(oneTimeKeysCounts));
        const setUnusedFallbackKeys = unusedFallbackKeys && new Set<string>(unusedFallbackKeys);

        if (mapOneTimeKeysCount !== undefined || setUnusedFallbackKeys !== undefined) {
            await this.receiveSyncChanges({
                oneTimeKeysCounts: mapOneTimeKeysCount,
                unusedFallbackKeys: setUnusedFallbackKeys,
            });
        }
    }

    /** called by the sync loop to process the notification that device lists have
     * been changed.
     *
     * @param deviceLists - device_lists field from /sync
     */
    public async processDeviceLists(deviceLists: IDeviceLists): Promise<void> {
        const devices = new RustSdkCryptoJs.DeviceLists(
            deviceLists.changed?.map((userId) => new RustSdkCryptoJs.UserId(userId)),
            deviceLists.left?.map((userId) => new RustSdkCryptoJs.UserId(userId)),
        );
        await this.receiveSyncChanges({ devices });
    }

    /** called by the sync loop on m.room.encrypted events
     *
     * @param room - in which the event was received
     * @param event - encryption event to be processed
     */
    public async onCryptoEvent(room: Room, event: MatrixEvent): Promise<void> {
        const config = event.getContent();

        const existingEncryptor = this.roomEncryptors[room.roomId];
        if (existingEncryptor) {
            existingEncryptor.onCryptoEvent(config);
        } else {
            this.roomEncryptors[room.roomId] = new RoomEncryptor(
                this.olmMachine,
                this.keyClaimManager,
                this.outgoingRequestsManager,
                room,
                config,
            );
        }
    }

    /** called by the sync loop after processing each sync.
     *
     * TODO: figure out something equivalent for sliding sync.
     *
     * @param syncState - information on the completed sync.
     */
    public onSyncCompleted(syncState: OnSyncCompletedData): void {
        // Processing the /sync may have produced new outgoing requests which need sending, so kick off the outgoing
        // request loop, if it's not already running.
        this.outgoingRequestsManager.doProcessOutgoingRequests().catch((e) => {
            this.logger.warn("onSyncCompleted: Error processing outgoing requests", e);
        });
    }

    /**
     * Handle an incoming m.key.verification request event
     *
     * @param sender - the sender of the event
     * @param content - the content of the event
     */
    private onIncomingKeyVerificationRequest(sender: string, content: IContent): void {
        const transactionId = content.transaction_id;
        if (!transactionId || !sender) {
            // not a valid request: ignore
            return;
        }

        const request: RustSdkCryptoJs.VerificationRequest | undefined = this.olmMachine.getVerificationRequest(
            new RustSdkCryptoJs.UserId(sender),
            transactionId,
        );

        if (request) {
            this.emit(
                CryptoEvent.VerificationRequestReceived,
                new RustVerificationRequest(
                    this.olmMachine,
                    request,
                    this.outgoingRequestProcessor,
                    this._supportedVerificationMethods,
                ),
            );
        }
    }

    ///////////////////////////////////////////////////////////////////////////////////////////////////////////////////
    //
    // Other public functions
    //
    ///////////////////////////////////////////////////////////////////////////////////////////////////////////////////

    /** called by the MatrixClient on a room membership event
     *
     * @param event - The matrix event which caused this event to fire.
     * @param member - The member whose RoomMember.membership changed.
     * @param oldMembership - The previous membership state. Null if it's a new member.
     */
    public onRoomMembership(event: MatrixEvent, member: RoomMember, oldMembership?: string): void {
        const enc = this.roomEncryptors[event.getRoomId()!];
        if (!enc) {
            // not encrypting in this room
            return;
        }
        enc.onRoomMembership(member);
    }

    /** Callback for OlmMachine.registerRoomKeyUpdatedCallback
     *
     * Called by the rust-sdk whenever there is an update to (megolm) room keys. We
     * check if we have any events waiting for the given keys, and schedule them for
     * a decryption retry if so.
     *
     * @param keys - details of the updated keys
     */
    public async onRoomKeysUpdated(keys: RustSdkCryptoJs.RoomKeyInfo[]): Promise<void> {
        for (const key of keys) {
            this.onRoomKeyUpdated(key);
        }
        this.backupManager.maybeUploadKey();
    }

    private onRoomKeyUpdated(key: RustSdkCryptoJs.RoomKeyInfo): void {
        if (this.stopped) return;
        this.logger.debug(
            `Got update for session ${key.senderKey.toBase64()}|${key.sessionId} in ${key.roomId.toString()}`,
        );
        const pendingList = this.eventDecryptor.getEventsPendingRoomKey(key);
        if (pendingList.length === 0) return;

        this.logger.debug(
            "Retrying decryption on events:",
            pendingList.map((e) => `${e.getId()}`),
        );

        // Have another go at decrypting events with this key.
        //
        // We don't want to end up blocking the callback from Rust, which could otherwise end up dropping updates,
        // so we don't wait for the decryption to complete. In any case, there is no need to wait:
        // MatrixEvent.attemptDecryption ensures that there is only one decryption attempt happening at once,
        // and deduplicates repeated attempts for the same event.
        for (const ev of pendingList) {
            ev.attemptDecryption(this, { isRetry: true }).catch((_e) => {
                this.logger.info(`Still unable to decrypt event ${ev.getId()} after receiving key`);
            });
        }
    }

    /**
     * Callback for `OlmMachine.registerUserIdentityUpdatedCallback`
     *
     * Called by the rust-sdk whenever there is an update to any user's cross-signing status. We re-check their trust
     * status and emit a `UserTrustStatusChanged` event.
     *
     * @param userId - the user with the updated identity
     */
    public async onUserIdentityUpdated(userId: RustSdkCryptoJs.UserId): Promise<void> {
        const newVerification = await this.getUserVerificationStatus(userId.toString());
        this.emit(CryptoEvent.UserTrustStatusChanged, userId.toString(), newVerification);

        // If our own user identity has changed, we may now trust the key backup where we did not before.
        // So, re-check the key backup status and enable it if available.
        if (userId.toString() === this.userId) {
            await this.checkKeyBackupAndEnable();
        }
    }

    /**
     * Handles secret received from the rust secret inbox.
     *
     * The gossipped secrets are received using the `m.secret.send` event type
     * and are guaranteed to have been received over a 1-to-1 Olm
     * Session from a verified device.
     *
     * The only secret currently handled in this way is `m.megolm_backup.v1`.
     *
     * @param name - the secret name
     * @param value - the secret value
     */
    private async handleSecretReceived(name: string, value: string): Promise<boolean> {
        this.logger.debug(`onReceiveSecret: Received secret ${name}`);
        if (name === "m.megolm_backup.v1") {
            return await this.backupManager.handleBackupSecretReceived(value);
            // XXX at this point we should probably try to download the backup and import the keys,
            // or at least retry for the current decryption failures?
            // Maybe add some signaling when a new secret is received, and let clients handle it?
            // as it's where the restore from backup APIs are exposed.
        }
        return false;
    }

    /**
     * Called when a new secret is received in the rust secret inbox.
     *
     * Will poll the secret inbox and handle the secrets received.
     *
     * @param name - The name of the secret received.
     */
    public async checkSecrets(name: string): Promise<void> {
        const pendingValues: string[] = await this.olmMachine.getSecretsFromInbox(name);
        for (const value of pendingValues) {
            if (await this.handleSecretReceived(name, value)) {
                // If we have a valid secret for that name there is no point of processing the other secrets values.
                // It's probably the same secret shared by another device.
                break;
            }
        }

        // Important to call this after handling the secrets as good hygiene.
        await this.olmMachine.deleteSecretsFromInbox(name);
    }

    /**
     * Handle a live event received via /sync.
     * See {@link ClientEventHandlerMap#event}
     *
     * @param event - live event
     */
    public async onLiveEventFromSync(event: MatrixEvent): Promise<void> {
        // Ignore state event or remote echo
        // transaction_id is provided in case of remote echo {@link https://spec.matrix.org/v1.7/client-server-api/#local-echo}
        if (event.isState() || !!event.getUnsigned().transaction_id) return;

        const processEvent = async (evt: MatrixEvent): Promise<void> => {
            // Process only verification event
            if (isVerificationEvent(event)) {
                await this.onKeyVerificationRequest(evt);
            }
        };

        // If the event is encrypted of in failure, we wait for decryption
        if (event.isDecryptionFailure() || event.isEncrypted()) {
            // 5 mins
            const TIMEOUT_DELAY = 5 * 60 * 1000;

            // After 5mins, we are not expecting the event to be decrypted
            const timeoutId = setTimeout(() => event.off(MatrixEventEvent.Decrypted, onDecrypted), TIMEOUT_DELAY);

            const onDecrypted = (decryptedEvent: MatrixEvent, error?: Error): void => {
                if (error) return;

                clearTimeout(timeoutId);
                event.off(MatrixEventEvent.Decrypted, onDecrypted);
                processEvent(decryptedEvent);
            };

            event.on(MatrixEventEvent.Decrypted, onDecrypted);
        } else {
            await processEvent(event);
        }
    }

    /**
     * Handle key verification request.
     *
     * @param event - a key validation request event.
     */
    private async onKeyVerificationRequest(event: MatrixEvent): Promise<void> {
        const roomId = event.getRoomId();

        if (!roomId) {
            throw new Error("missing roomId in the event");
        }

        this.logger.debug(
            `Incoming verification event ${event.getId()} type ${event.getType()} from ${event.getSender()}`,
        );

        await this.olmMachine.receiveVerificationEvent(
            JSON.stringify({
                event_id: event.getId(),
                type: event.getType(),
                sender: event.getSender(),
                state_key: event.getStateKey(),
                content: event.getContent(),
                origin_server_ts: event.getTs(),
            }),
            new RustSdkCryptoJs.RoomId(roomId),
        );

        if (
            event.getType() === EventType.RoomMessage &&
            event.getContent().msgtype === MsgType.KeyVerificationRequest
        ) {
            const request: RustSdkCryptoJs.VerificationRequest | undefined = this.olmMachine.getVerificationRequest(
                new RustSdkCryptoJs.UserId(event.getSender()!),
                event.getId()!,
            );

            if (!request) {
                // There are multiple reasons this can happen; probably the most likely is that the event is too old.
                this.logger.info(
                    `Ignoring just-received verification request ${event.getId()} which did not start a rust-side verification`,
                );
            } else {
                this.emit(
                    CryptoEvent.VerificationRequestReceived,
                    new RustVerificationRequest(
                        this.olmMachine,
                        request,
                        this.outgoingRequestProcessor,
                        this._supportedVerificationMethods,
                    ),
                );
            }
        }

        // that may have caused us to queue up outgoing requests, so make sure we send them.
        this.outgoingRequestsManager.doProcessOutgoingRequests().catch((e) => {
            this.logger.warn("onKeyVerificationRequest: Error processing outgoing requests", e);
        });
    }
}

class EventDecryptor {
    /**
     * Events which we couldn't decrypt due to unknown sessions / indexes.
     *
     * Map from senderKey to sessionId to Set of MatrixEvents
     */
    private eventsPendingKey = new MapWithDefault<string, MapWithDefault<string, Set<MatrixEvent>>>(
        () => new MapWithDefault<string, Set<MatrixEvent>>(() => new Set()),
    );

    public constructor(
        private readonly logger: Logger,
        private readonly olmMachine: RustSdkCryptoJs.OlmMachine,
        private readonly perSessionBackupDownloader: PerSessionKeyBackupDownloader,
    ) {}

    public async attemptEventDecryption(event: MatrixEvent): Promise<IEventDecryptionResult> {
        // add the event to the pending list *before* attempting to decrypt.
        // then, if the key turns up while decryption is in progress (and
        // decryption fails), we will schedule a retry.
        // (fixes https://github.com/vector-im/element-web/issues/5001)
        this.addEventToPendingList(event);

        try {
            const res = (await this.olmMachine.decryptRoomEvent(
                stringifyEvent(event),
                new RustSdkCryptoJs.RoomId(event.getRoomId()!),
            )) as RustSdkCryptoJs.DecryptedRoomEvent;

            // Success. We can remove the event from the pending list, if
            // that hasn't already happened.
            this.removeEventFromPendingList(event);

            return {
                clearEvent: JSON.parse(res.event),
                claimedEd25519Key: res.senderClaimedEd25519Key,
                senderCurve25519Key: res.senderCurve25519Key,
                forwardingCurve25519KeyChain: res.forwardingCurve25519KeyChain,
            };
        } catch (err) {
            // We need to map back to regular decryption errors (used for analytics for example)
            // The DecryptionErrors are used by react-sdk so is implicitly part of API, but poorly typed
            if (err instanceof RustSdkCryptoJs.MegolmDecryptionError) {
                const content = event.getWireContent();
                let jsError;
                switch (err.code) {
                    case RustSdkCryptoJs.DecryptionErrorCode.MissingRoomKey: {
                        jsError = new DecryptionError(
                            "MEGOLM_UNKNOWN_INBOUND_SESSION_ID",
                            "The sender's device has not sent us the keys for this message.",
                            {
                                session: content.sender_key + "|" + content.session_id,
                            },
                        );
                        this.perSessionBackupDownloader.onDecryptionKeyMissingError(
                            event.getRoomId()!,
                            event.getWireContent().session_id!,
                        );
                        break;
                    }
                    case RustSdkCryptoJs.DecryptionErrorCode.UnknownMessageIndex: {
                        jsError = new DecryptionError(
                            "OLM_UNKNOWN_MESSAGE_INDEX",
                            "The sender's device has not sent us the keys for this message at this index.",
                            {
                                session: content.sender_key + "|" + content.session_id,
                            },
                        );
                        this.perSessionBackupDownloader.onDecryptionKeyMissingError(
                            event.getRoomId()!,
                            event.getWireContent().session_id!,
                        );
                        break;
                    }
                    // We don't map MismatchedIdentityKeys for now, as there is no equivalent in legacy.
                    // Just put it on the `UNABLE_TO_DECRYPT` bucket.
                    default: {
                        jsError = new DecryptionError("UNABLE_TO_DECRYPT", err.description, {
                            session: content.sender_key + "|" + content.session_id,
                        });
                        break;
                    }
                }
                throw jsError;
            }
            throw new DecryptionError("UNABLE_TO_DECRYPT", "Unknown error");
        }
    }

    public async getEncryptionInfoForEvent(event: MatrixEvent): Promise<EventEncryptionInfo | null> {
        if (!event.getClearContent() || event.isDecryptionFailure()) {
            // not successfully decrypted
            return null;
        }

        // special-case outgoing events, which the rust crypto-sdk will barf on
        if (event.status !== null) {
            return { shieldColour: EventShieldColour.NONE, shieldReason: null };
        }

        const encryptionInfo = await this.olmMachine.getRoomEventEncryptionInfo(
            stringifyEvent(event),
            new RustSdkCryptoJs.RoomId(event.getRoomId()!),
        );

        return rustEncryptionInfoToJsEncryptionInfo(this.logger, encryptionInfo);
    }

    /**
     * Look for events which are waiting for a given megolm session
     *
     * Returns a list of events which were encrypted by `session` and could not be decrypted
     *
     * @param session -
     */
    public getEventsPendingRoomKey(session: RustSdkCryptoJs.RoomKeyInfo): MatrixEvent[] {
        const senderPendingEvents = this.eventsPendingKey.get(session.senderKey.toBase64());
        if (!senderPendingEvents) return [];

        const sessionPendingEvents = senderPendingEvents.get(session.sessionId);
        if (!sessionPendingEvents) return [];

        const roomId = session.roomId.toString();
        return [...sessionPendingEvents].filter((ev) => ev.getRoomId() === roomId);
    }

    /**
     * Add an event to the list of those awaiting their session keys.
     */
    private addEventToPendingList(event: MatrixEvent): void {
        const content = event.getWireContent();
        const senderKey = content.sender_key;
        const sessionId = content.session_id;

        const senderPendingEvents = this.eventsPendingKey.getOrCreate(senderKey);
        const sessionPendingEvents = senderPendingEvents.getOrCreate(sessionId);
        sessionPendingEvents.add(event);
    }

    /**
     * Remove an event from the list of those awaiting their session keys.
     */
    private removeEventFromPendingList(event: MatrixEvent): void {
        const content = event.getWireContent();
        const senderKey = content.sender_key;
        const sessionId = content.session_id;

        const senderPendingEvents = this.eventsPendingKey.get(senderKey);
        if (!senderPendingEvents) return;

        const sessionPendingEvents = senderPendingEvents.get(sessionId);
        if (!sessionPendingEvents) return;

        sessionPendingEvents.delete(event);

        // also clean up the higher-level maps if they are now empty
        if (sessionPendingEvents.size === 0) {
            senderPendingEvents.delete(sessionId);
            if (senderPendingEvents.size === 0) {
                this.eventsPendingKey.delete(senderKey);
            }
        }
    }
}

function stringifyEvent(event: MatrixEvent): string {
    return JSON.stringify({
        event_id: event.getId(),
        type: event.getWireType(),
        sender: event.getSender(),
        state_key: event.getStateKey(),
        content: event.getWireContent(),
        origin_server_ts: event.getTs(),
    });
}

function rustEncryptionInfoToJsEncryptionInfo(
    logger: Logger,
    encryptionInfo: RustSdkCryptoJs.EncryptionInfo | undefined,
): EventEncryptionInfo | null {
    if (encryptionInfo === undefined) {
        // not decrypted here
        return null;
    }

    // TODO: use strict shield semantics.
    const shieldState = encryptionInfo.shieldState(false);

    let shieldColour: EventShieldColour;
    switch (shieldState.color) {
        case RustSdkCryptoJs.ShieldColor.Grey:
            shieldColour = EventShieldColour.GREY;
            break;
        case RustSdkCryptoJs.ShieldColor.None:
            shieldColour = EventShieldColour.NONE;
            break;
        default:
            shieldColour = EventShieldColour.RED;
    }

    let shieldReason: EventShieldReason | null;
    if (shieldState.message === undefined) {
        shieldReason = null;
    } else if (shieldState.message === "Encrypted by an unverified user.") {
        // this case isn't actually used with lax shield semantics.
        shieldReason = EventShieldReason.UNVERIFIED_IDENTITY;
    } else if (shieldState.message === "Encrypted by a device not verified by its owner.") {
        shieldReason = EventShieldReason.UNSIGNED_DEVICE;
    } else if (
        shieldState.message === "The authenticity of this encrypted message can't be guaranteed on this device."
    ) {
        shieldReason = EventShieldReason.AUTHENTICITY_NOT_GUARANTEED;
    } else if (shieldState.message === "Encrypted by an unknown or deleted device.") {
        shieldReason = EventShieldReason.UNKNOWN_DEVICE;
    } else {
        logger.warn(`Unknown shield state message '${shieldState.message}'`);
        shieldReason = EventShieldReason.UNKNOWN;
    }

    return { shieldColour, shieldReason };
}

type RustCryptoEvents =
    | CryptoEvent.VerificationRequestReceived
    | CryptoEvent.UserTrustStatusChanged
    | RustBackupCryptoEvents;

type RustCryptoEventMap = {
    /**
     * Fires when a key verification request is received.
     */
    [CryptoEvent.VerificationRequestReceived]: (request: VerificationRequest) => void;

    /**
     * Fires when the trust status of a user changes.
     */
    [CryptoEvent.UserTrustStatusChanged]: (userId: string, userTrustLevel: UserVerificationStatus) => void;

    [CryptoEvent.KeyBackupDecryptionKeyCached]: (version: string) => void;
} & RustBackupCryptoEventMap;