// Copyright 2020 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.

mod share_strategy;

use std::{
    collections::{BTreeMap, BTreeSet},
    fmt::Debug,
    iter,
    iter::zip,
    sync::Arc,
};

use futures_util::future::join_all;
use itertools::Itertools;
use matrix_sdk_common::{
    deserialized_responses::WithheldCode, executor::spawn, locks::RwLock as StdRwLock,
};
use ruma::{
    events::{AnyMessageLikeEventContent, AnyToDeviceEventContent, ToDeviceEventType},
    serde::Raw,
    to_device::DeviceIdOrAllDevices,
    DeviceId, OwnedDeviceId, OwnedRoomId, OwnedTransactionId, OwnedUserId, RoomId, TransactionId,
    UserId,
};
use serde::Serialize;
pub(crate) use share_strategy::CollectRecipientsResult;
pub use share_strategy::CollectStrategy;
use tracing::{debug, error, info, instrument, trace, warn, Instrument};

use crate::{
    error::{EventError, MegolmResult, OlmResult},
    identities::device::MaybeEncryptedRoomKey,
    olm::{
        InboundGroupSession, OutboundGroupSession, SenderData, SenderDataFinder, Session,
        ShareInfo, ShareState,
    },
    store::{Changes, CryptoStoreWrapper, Result as StoreResult, Store},
    types::{
        events::{
            room::encrypted::{RoomEncryptedEventContent, ToDeviceEncryptedEventContent},
            room_key_bundle::RoomKeyBundleContent,
            EventType,
        },
        requests::ToDeviceRequest,
    },
    Device, DeviceData, EncryptionSettings, OlmError,
};

#[derive(Clone, Debug)]
pub(crate) struct GroupSessionCache {
    store: Store,
    sessions: Arc<StdRwLock<BTreeMap<OwnedRoomId, OutboundGroupSession>>>,
    /// A map from the request id to the group session that the request belongs
    /// to. Used to mark requests belonging to the session as shared.
    sessions_being_shared: Arc<StdRwLock<BTreeMap<OwnedTransactionId, OutboundGroupSession>>>,
}

impl GroupSessionCache {
    pub(crate) fn new(store: Store) -> Self {
        Self { store, sessions: Default::default(), sessions_being_shared: Default::default() }
    }

    pub(crate) fn insert(&self, session: OutboundGroupSession) {
        self.sessions.write().insert(session.room_id().to_owned(), session);
    }

    /// Either get a session for the given room from the cache or load it from
    /// the store.
    ///
    /// # Arguments
    ///
    /// * `room_id` - The id of the room this session is used for.
    pub async fn get_or_load(&self, room_id: &RoomId) -> Option<OutboundGroupSession> {
        // Get the cached session, if there isn't one load one from the store
        // and put it in the cache.
        if let Some(s) = self.sessions.read().get(room_id) {
            return Some(s.clone());
        }

        match self.store.get_outbound_group_session(room_id).await {
            Ok(Some(s)) => {
                {
                    let mut sessions_being_shared = self.sessions_being_shared.write();
                    for request_id in s.pending_request_ids() {
                        sessions_being_shared.insert(request_id, s.clone());
                    }
                }

                self.sessions.write().insert(room_id.to_owned(), s.clone());

                Some(s)
            }
            Ok(None) => None,
            Err(e) => {
                error!("Couldn't restore an outbound group session: {e:?}");
                None
            }
        }
    }

    /// Get an outbound group session for a room, if one exists.
    ///
    /// # Arguments
    ///
    /// * `room_id` - The id of the room for which we should get the outbound
    ///   group session.
    fn get(&self, room_id: &RoomId) -> Option<OutboundGroupSession> {
        self.sessions.read().get(room_id).cloned()
    }

    /// Returns whether any session is withheld with the given device and code.
    fn has_session_withheld_to(&self, device: &DeviceData, code: &WithheldCode) -> bool {
        self.sessions.read().values().any(|s| s.sharing_view().is_withheld_to(device, code))
    }

    fn remove_from_being_shared(&self, id: &TransactionId) -> Option<OutboundGroupSession> {
        self.sessions_being_shared.write().remove(id)
    }

    fn mark_as_being_shared(&self, id: OwnedTransactionId, session: OutboundGroupSession) {
        self.sessions_being_shared.write().insert(id, session);
    }
}

#[derive(Debug, Clone)]
pub(crate) struct GroupSessionManager {
    /// Store for the encryption keys.
    /// Persists all the encryption keys so a client can resume the session
    /// without the need to create new keys.
    store: Store,
    /// The currently active outbound group sessions.
    sessions: GroupSessionCache,
}

impl GroupSessionManager {
    const MAX_TO_DEVICE_MESSAGES: usize = 250;

    pub fn new(store: Store) -> Self {
        Self { store: store.clone(), sessions: GroupSessionCache::new(store) }
    }

    pub async fn invalidate_group_session(&self, room_id: &RoomId) -> StoreResult<bool> {
        if let Some(s) = self.sessions.get(room_id) {
            s.invalidate_session();

            let mut changes = Changes::default();
            changes.outbound_group_sessions.push(s.clone());
            self.store.save_changes(changes).await?;

            Ok(true)
        } else {
            Ok(false)
        }
    }

    pub async fn mark_request_as_sent(&self, request_id: &TransactionId) -> StoreResult<()> {
        let Some(session) = self.sessions.remove_from_being_shared(request_id) else {
            return Ok(());
        };

        let no_olm = session.mark_request_as_sent(request_id);

        let mut changes = Changes::default();

        for (user_id, devices) in &no_olm {
            for device_id in devices {
                let device = self.store.get_device(user_id, device_id).await;

                if let Ok(Some(device)) = device {
                    device.mark_withheld_code_as_sent();
                    changes.devices.changed.push(device.inner.clone());
                } else {
                    error!(
                        ?request_id,
                        "Marking to-device no olm as sent but device not found, might \
                            have been deleted?"
                    );
                }
            }
        }

        changes.outbound_group_sessions.push(session.clone());
        self.store.save_changes(changes).await
    }

    #[cfg(test)]
    pub fn get_outbound_group_session(&self, room_id: &RoomId) -> Option<OutboundGroupSession> {
        self.sessions.get(room_id)
    }

    pub async fn encrypt(
        &self,
        room_id: &RoomId,
        event_type: &str,
        content: &Raw<AnyMessageLikeEventContent>,
    ) -> MegolmResult<Raw<RoomEncryptedEventContent>> {
        let session =
            self.sessions.get_or_load(room_id).await.expect("Session wasn't created nor shared");

        assert!(!session.expired(), "Session expired");

        let content = session.encrypt(event_type, content).await;

        let mut changes = Changes::default();
        changes.outbound_group_sessions.push(session);
        self.store.save_changes(changes).await?;

        Ok(content)
    }

    /// Create a new outbound group session.
    ///
    /// This also creates a matching inbound group session.
    pub async fn create_outbound_group_session(
        &self,
        room_id: &RoomId,
        settings: EncryptionSettings,
        own_sender_data: SenderData,
    ) -> OlmResult<(OutboundGroupSession, InboundGroupSession)> {
        let (outbound, inbound) = self
            .store
            .static_account()
            .create_group_session_pair(room_id, settings, own_sender_data)
            .await
            .map_err(|_| EventError::UnsupportedAlgorithm)?;

        self.sessions.insert(outbound.clone());
        Ok((outbound, inbound))
    }

    pub async fn get_or_create_outbound_session(
        &self,
        room_id: &RoomId,
        settings: EncryptionSettings,
        own_sender_data: SenderData,
    ) -> OlmResult<(OutboundGroupSession, Option<InboundGroupSession>)> {
        let outbound_session = self.sessions.get_or_load(room_id).await;

        // If there is no session or the session has expired or is invalid,
        // create a new one.
        if let Some(s) = outbound_session {
            if s.expired() || s.invalidated() {
                self.create_outbound_group_session(room_id, settings, own_sender_data)
                    .await
                    .map(|(o, i)| (o, i.into()))
            } else {
                Ok((s, None))
            }
        } else {
            self.create_outbound_group_session(room_id, settings, own_sender_data)
                .await
                .map(|(o, i)| (o, i.into()))
        }
    }

    /// Encrypt the given group session key for the given devices and create
    /// to-device requests that sends the encrypted content to them.
    ///
    /// See also [`encrypt_content_for_devices`] which is similar
    /// but is not specific to group sessions, and does not return the
    /// [`ShareInfo`] data.
    async fn encrypt_session_for(
        store: Arc<CryptoStoreWrapper>,
        group_session: OutboundGroupSession,
        devices: Vec<DeviceData>,
    ) -> OlmResult<(
        EncryptForDevicesResult,
        BTreeMap<OwnedUserId, BTreeMap<OwnedDeviceId, ShareInfo>>,
    )> {
        // Use a named type instead of a tuple with rather long type name
        pub struct DeviceResult {
            device: DeviceData,
            maybe_encrypted_room_key: MaybeEncryptedRoomKey,
        }

        let mut result_builder = EncryptForDevicesResultBuilder::default();
        let mut share_infos = BTreeMap::new();

        // XXX is there a way to do this that doesn't involve cloning the
        // `Arc<CryptoStoreWrapper>` for each device?
        let encrypt = |store: Arc<CryptoStoreWrapper>,
                       device: DeviceData,
                       session: OutboundGroupSession| async move {
            let encryption_result = device.maybe_encrypt_room_key(store.as_ref(), session).await?;

            Ok::<_, OlmError>(DeviceResult { device, maybe_encrypted_room_key: encryption_result })
        };

        let tasks: Vec<_> = devices
            .iter()
            .map(|d| spawn(encrypt(store.clone(), d.clone(), group_session.clone())))
            .collect();

        let results = join_all(tasks).await;

        for result in results {
            let result = result.expect("Encryption task panicked")?;

            match result.maybe_encrypted_room_key {
                MaybeEncryptedRoomKey::Encrypted { used_session, share_info, message } => {
                    result_builder.on_successful_encryption(&result.device, *used_session, message);

                    let user_id = result.device.user_id().to_owned();
                    let device_id = result.device.device_id().to_owned();
                    share_infos
                        .entry(user_id)
                        .or_insert_with(BTreeMap::new)
                        .insert(device_id, *share_info);
                }
                MaybeEncryptedRoomKey::MissingSession => {
                    result_builder.on_missing_session(result.device);
                }
            }
        }

        Ok((result_builder.into_result(), share_infos))
    }

    /// Given a list of user and an outbound session, return the list of users
    /// and their devices that this session should be shared with.
    ///
    /// Returns information indicating whether the session needs to be rotated
    /// and the list of users/devices that should receive or not the session
    /// (with withheld reason).
    #[instrument(skip_all)]
    pub async fn collect_session_recipients(
        &self,
        users: impl Iterator<Item = &UserId>,
        settings: &EncryptionSettings,
        outbound: &OutboundGroupSession,
    ) -> OlmResult<CollectRecipientsResult> {
        share_strategy::collect_session_recipients(&self.store, users, settings, outbound).await
    }

    async fn encrypt_request(
        store: Arc<CryptoStoreWrapper>,
        chunk: Vec<DeviceData>,
        outbound: OutboundGroupSession,
        sessions: GroupSessionCache,
    ) -> OlmResult<(Vec<Session>, Vec<(DeviceData, WithheldCode)>)> {
        let (result, share_infos) =
            Self::encrypt_session_for(store, outbound.clone(), chunk).await?;

        if let Some(request) = result.to_device_request {
            let id = request.txn_id.clone();
            outbound.add_request(id.clone(), request.into(), share_infos);
            sessions.mark_as_being_shared(id, outbound.clone());
        }

        Ok((result.updated_olm_sessions, result.no_olm_devices))
    }

    pub(crate) fn session_cache(&self) -> GroupSessionCache {
        self.sessions.clone()
    }

    async fn maybe_rotate_group_session(
        &self,
        should_rotate: bool,
        room_id: &RoomId,
        outbound: OutboundGroupSession,
        encryption_settings: EncryptionSettings,
        changes: &mut Changes,
        own_device: Option<Device>,
    ) -> OlmResult<OutboundGroupSession> {
        Ok(if should_rotate {
            let old_session_id = outbound.session_id();

            let (outbound, mut inbound) = self
                .create_outbound_group_session(room_id, encryption_settings, SenderData::unknown())
                .await?;

            // Use our own device info to populate the SenderData that validates the
            // InboundGroupSession that we create as a pair to the OutboundGroupSession we
            // are sending out.
            let own_sender_data = if let Some(device) = own_device {
                SenderDataFinder::find_using_device_data(
                    &self.store,
                    device.inner.clone(),
                    &inbound,
                )
                .await?
            } else {
                error!("Unable to find our own device!");
                SenderData::unknown()
            };
            inbound.sender_data = own_sender_data;

            changes.outbound_group_sessions.push(outbound.clone());
            changes.inbound_group_sessions.push(inbound);

            debug!(
                old_session_id = old_session_id,
                session_id = outbound.session_id(),
                "A user or device has left the room since we last sent a \
                message, or the encryption settings have changed. Rotating the \
                room key.",
            );

            outbound
        } else {
            outbound
        })
    }

    async fn encrypt_for_devices(
        &self,
        recipient_devices: Vec<DeviceData>,
        group_session: &OutboundGroupSession,
        changes: &mut Changes,
    ) -> OlmResult<Vec<(DeviceData, WithheldCode)>> {
        // If we have some recipients, log them here.
        if !recipient_devices.is_empty() {
            let recipients = recipient_list_to_users_and_devices(&recipient_devices);

            // If there are new recipients we need to persist the outbound group
            // session as the to-device requests are persisted with the session.
            changes.outbound_group_sessions = vec![group_session.clone()];

            let message_index = group_session.message_index().await;

            info!(
                ?recipients,
                message_index,
                room_id = ?group_session.room_id(),
                session_id = group_session.session_id(),
                "Trying to encrypt a room key",
            );
        }

        // Chunk the recipients out so each to-device request will contain a
        // limited amount of to-device messages.
        //
        // Create concurrent tasks for each chunk of recipients.
        let tasks: Vec<_> = recipient_devices
            .chunks(Self::MAX_TO_DEVICE_MESSAGES)
            .map(|chunk| {
                spawn(Self::encrypt_request(
                    self.store.crypto_store(),
                    chunk.to_vec(),
                    group_session.clone(),
                    self.sessions.clone(),
                ))
            })
            .collect();

        let mut withheld_devices = Vec::new();

        // Wait for all the tasks to finish up and queue up the Olm session that
        // was used to encrypt the room key to be persisted again. This is
        // needed because each encryption step will mutate the Olm session,
        // ratcheting its state forward.
        for result in join_all(tasks).await {
            let result = result.expect("Encryption task panicked");

            let (used_sessions, failed_no_olm) = result?;

            changes.sessions.extend(used_sessions);
            withheld_devices.extend(failed_no_olm);
        }

        Ok(withheld_devices)
    }

    fn is_withheld_to(
        &self,
        group_session: &OutboundGroupSession,
        device: &DeviceData,
        code: &WithheldCode,
    ) -> bool {
        // The `m.no_olm` withheld code is special because it is supposed to be sent
        // only once for a given device. The `Device` remembers the flag if we
        // already sent a `m.no_olm` to this particular device so let's check
        // that first.
        //
        // Keep in mind that any outbound group session might want to send this code to
        // the device. So we need to check if any of our outbound group sessions
        // is attempting to send the code to the device.
        //
        // This still has a slight race where some other thread might remove the
        // outbound group session while a third is marking the device as having
        // received the code.
        //
        // Since nothing terrible happens if we do end up sending the withheld code
        // twice, and removing the race requires us to lock the store because the
        // `OutboundGroupSession` and the `Device` both interact with the flag we'll
        // leave it be.
        if code == &WithheldCode::NoOlm {
            device.was_withheld_code_sent() || self.sessions.has_session_withheld_to(device, code)
        } else {
            group_session.sharing_view().is_withheld_to(device, code)
        }
    }

    fn handle_withheld_devices(
        &self,
        group_session: &OutboundGroupSession,
        withheld_devices: Vec<(DeviceData, WithheldCode)>,
    ) -> OlmResult<()> {
        // Convert a withheld code for the group session into a to-device event content.
        let to_content = |code| {
            let content = group_session.withheld_code(code);
            Raw::new(&content).expect("We can always serialize a withheld content info").cast()
        };

        // Helper to convert a chunk of device and withheld code pairs into a to-device
        // request and it's accompanying share info.
        let chunk_to_request = |chunk| {
            let mut messages = BTreeMap::new();
            let mut share_infos = BTreeMap::new();

            for (device, code) in chunk {
                let device: DeviceData = device;
                let code: WithheldCode = code;

                let user_id = device.user_id().to_owned();
                let device_id = device.device_id().to_owned();

                let share_info = ShareInfo::new_withheld(code.to_owned());
                let content = to_content(code);

                messages
                    .entry(user_id.to_owned())
                    .or_insert_with(BTreeMap::new)
                    .insert(DeviceIdOrAllDevices::DeviceId(device_id.to_owned()), content);

                share_infos
                    .entry(user_id)
                    .or_insert_with(BTreeMap::new)
                    .insert(device_id, share_info);
            }

            let txn_id = TransactionId::new();

            let request = ToDeviceRequest {
                event_type: ToDeviceEventType::from("m.room_key.withheld"),
                txn_id,
                messages,
            };

            (request, share_infos)
        };

        let result: Vec<_> = withheld_devices
            .into_iter()
            .filter(|(device, code)| !self.is_withheld_to(group_session, device, code))
            .chunks(Self::MAX_TO_DEVICE_MESSAGES)
            .into_iter()
            .map(chunk_to_request)
            .collect();

        for (request, share_info) in result {
            if !request.messages.is_empty() {
                let txn_id = request.txn_id.to_owned();
                group_session.add_request(txn_id.to_owned(), request.into(), share_info);

                self.sessions.mark_as_being_shared(txn_id, group_session.clone());
            }
        }

        Ok(())
    }

    fn log_room_key_sharing_result(requests: &[Arc<ToDeviceRequest>]) {
        for request in requests {
            let message_list = Self::to_device_request_to_log_list(request);
            info!(
                request_id = ?request.txn_id,
                ?message_list,
                "Created batch of to-device messages of type {}",
                request.event_type
            );
        }
    }

    /// Given a to-device request, build a recipient map suitable for logging.
    ///
    /// Returns a list of triples of (message_id, user id, device_id).
    fn to_device_request_to_log_list(
        request: &Arc<ToDeviceRequest>,
    ) -> Vec<(String, String, String)> {
        #[derive(serde::Deserialize)]
        struct ContentStub<'a> {
            #[serde(borrow, default, rename = "org.matrix.msgid")]
            message_id: Option<&'a str>,
        }

        let mut result: Vec<(String, String, String)> = Vec::new();

        for (user_id, device_map) in &request.messages {
            for (device, content) in device_map {
                let message_id: Option<&str> = content
                    .deserialize_as::<ContentStub<'_>>()
                    .expect("We should be able to deserialize the content we generated")
                    .message_id;

                result.push((
                    message_id.unwrap_or("<undefined>").to_owned(),
                    user_id.to_string(),
                    device.to_string(),
                ));
            }
        }
        result
    }

    /// Get to-device requests to share a room key with users in a room.
    ///
    /// # Arguments
    ///
    /// `room_id` - The room id of the room where the room key will be used.
    ///
    /// `users` - The list of users that should receive the room key.
    ///
    /// `encryption_settings` - The settings that should be used for
    /// the room key.
    #[instrument(skip(self, users, encryption_settings), fields(session_id))]
    pub async fn share_room_key(
        &self,
        room_id: &RoomId,
        users: impl Iterator<Item = &UserId>,
        encryption_settings: impl Into<EncryptionSettings>,
    ) -> OlmResult<Vec<Arc<ToDeviceRequest>>> {
        trace!("Checking if a room key needs to be shared");

        let account = self.store.static_account();
        let device = self.store.get_device(account.user_id(), account.device_id()).await?;

        let encryption_settings = encryption_settings.into();
        let mut changes = Changes::default();

        // Try to get an existing session or create a new one.
        let (outbound, inbound) = self
            .get_or_create_outbound_session(
                room_id,
                encryption_settings.clone(),
                SenderData::unknown(),
            )
            .await?;
        tracing::Span::current().record("session_id", outbound.session_id());

        // Having an inbound group session here means that we created a new
        // group session pair, which we then need to store.
        if let Some(mut inbound) = inbound {
            // Use our own device info to populate the SenderData that validates the
            // InboundGroupSession that we create as a pair to the OutboundGroupSession we
            // are sending out.
            let own_sender_data = if let Some(device) = &device {
                SenderDataFinder::find_using_device_data(
                    &self.store,
                    device.inner.clone(),
                    &inbound,
                )
                .await?
            } else {
                error!("Unable to find our own device!");
                SenderData::unknown()
            };
            inbound.sender_data = own_sender_data;

            changes.outbound_group_sessions.push(outbound.clone());
            changes.inbound_group_sessions.push(inbound);
        }

        // Collect the recipient devices and check if either the settings
        // or the recipient list changed in a way that requires the
        // session to be rotated.
        let CollectRecipientsResult { should_rotate, devices, mut withheld_devices } =
            self.collect_session_recipients(users, &encryption_settings, &outbound).await?;

        let outbound = self
            .maybe_rotate_group_session(
                should_rotate,
                room_id,
                outbound,
                encryption_settings,
                &mut changes,
                device,
            )
            .await?;

        // Filter out the devices that already received this room key or have a
        // to-device message already queued up.
        let devices: Vec<_> = devices
            .into_iter()
            .flat_map(|(_, d)| {
                d.into_iter().filter(|d| match outbound.sharing_view().get_share_state(d) {
                    ShareState::NotShared => true,
                    ShareState::Shared { message_index: _, olm_wedging_index } => {
                        // If the recipient device's Olm wedging index is higher
                        // than the value that we stored with the session, that
                        // means that they tried to unwedge the session since we
                        // last shared the room key.  So we re-share it with
                        // them in case they weren't able to decrypt the room
                        // key the last time we shared it.
                        olm_wedging_index < d.olm_wedging_index
                    }
                    _ => false,
                })
            })
            .collect();

        // The `encrypt_for_devices()` method adds the to-device requests that will send
        // out the room key to the `OutboundGroupSession`. It doesn't do that
        // for the m.room_key_withheld events since we might have more of those
        // coming from the `collect_session_recipients()` method. Instead they get
        // returned by the method.
        let unable_to_encrypt_devices =
            self.encrypt_for_devices(devices, &outbound, &mut changes).await?;

        // Merge the withheld recipients.
        withheld_devices.extend(unable_to_encrypt_devices);

        // Now handle and add the withheld recipients to the resulting requests to the
        // `OutboundGroupSession`.
        self.handle_withheld_devices(&outbound, withheld_devices)?;

        // The to-device requests get added to the outbound group session, this
        // way we're making sure that they are persisted and scoped to the
        // session.
        let requests = outbound.pending_requests();

        if requests.is_empty() {
            if !outbound.shared() {
                debug!("The room key doesn't need to be shared with anyone. Marking as shared.");

                outbound.mark_as_shared();
                changes.outbound_group_sessions.push(outbound.clone());
            }
        } else {
            Self::log_room_key_sharing_result(&requests)
        }

        // Persist any changes we might have collected.
        if !changes.is_empty() {
            let session_count = changes.sessions.len();

            self.store.save_changes(changes).await?;

            trace!(
                session_count = session_count,
                "Stored the changed sessions after encrypting an room key"
            );
        }

        Ok(requests)
    }

    /// Collect the devices belonging to the given user, and send the details of
    /// a room key bundle to those devices.
    ///
    /// Returns a list of to-device requests which must be sent.
    ///
    /// For security reasons, only "safe" [`CollectStrategy`]s are supported, in
    /// which the recipient must have signed their
    /// devices. [`CollectStrategy::AllDevices`] and
    /// [`CollectStrategy::ErrorOnVerifiedUserProblem`] are "unsafe" in this
    /// respect,and are treated the same as
    /// [`CollectStrategy::IdentityBasedStrategy`].
    #[instrument(skip(self, bundle_data))]
    pub async fn share_room_key_bundle_data(
        &self,
        user_id: &UserId,
        collect_strategy: &CollectStrategy,
        bundle_data: RoomKeyBundleContent,
    ) -> OlmResult<Vec<ToDeviceRequest>> {
        // Only allow conservative sharing strategies
        let collect_strategy = match collect_strategy {
            CollectStrategy::AllDevices | CollectStrategy::ErrorOnVerifiedUserProblem => {
                warn!(
                    "Ignoring request to use unsafe sharing strategy {collect_strategy:?} \
                     for room key history sharing",
                );
                &CollectStrategy::IdentityBasedStrategy
            }
            CollectStrategy::IdentityBasedStrategy | CollectStrategy::OnlyTrustedDevices => {
                collect_strategy
            }
        };

        let mut changes = Changes::default();

        let CollectRecipientsResult { devices, .. } =
            share_strategy::collect_recipients_for_share_strategy(
                &self.store,
                iter::once(user_id),
                collect_strategy,
                None,
            )
            .await?;

        let devices = devices.into_values().flatten().collect();
        let event_type = bundle_data.event_type().to_owned();
        let (requests, _) = self
            .encrypt_content_for_devices(devices, &event_type, bundle_data, &mut changes)
            .await?;

        // TODO: figure out what to do with withheld devices

        // Persist any changes we might have collected.
        if !changes.is_empty() {
            let session_count = changes.sessions.len();

            self.store.save_changes(changes).await?;

            trace!(
                session_count = session_count,
                "Stored the changed sessions after encrypting an room key"
            );
        }

        Ok(requests)
    }

    /// Encrypt the given content for the given devices and build to-device
    /// requests to send the encrypted content to them.
    ///
    /// Returns a tuple containing (1) the list of to-device requests, and (2)
    /// the list of devices that we could not find an olm session for (so
    /// need a withheld message).
    pub(crate) async fn encrypt_content_for_devices(
        &self,
        recipient_devices: Vec<DeviceData>,
        event_type: &str,
        content: impl Serialize + Clone + Send + 'static,
        changes: &mut Changes,
    ) -> OlmResult<(Vec<ToDeviceRequest>, Vec<(DeviceData, WithheldCode)>)> {
        let recipients = recipient_list_to_users_and_devices(&recipient_devices);
        info!(?recipients, "Encrypting content of type {}", event_type);

        // Chunk the recipients out so each to-device request will contain a
        // limited amount of to-device messages.
        //
        // Create concurrent tasks for each chunk of recipients.
        let tasks: Vec<_> = recipient_devices
            .chunks(Self::MAX_TO_DEVICE_MESSAGES)
            .map(|chunk| {
                spawn(
                    encrypt_content_for_devices(
                        self.store.crypto_store(),
                        event_type.to_owned(),
                        content.clone(),
                        chunk.to_vec(),
                    )
                    .in_current_span(),
                )
            })
            .collect();

        let mut no_olm_devices = Vec::new();
        let mut to_device_requests = Vec::new();

        // Wait for all the tasks to finish up and queue up the Olm session that
        // was used to encrypt the room key to be persisted again. This is
        // needed because each encryption step will mutate the Olm session,
        // ratcheting its state forward.
        for result in join_all(tasks).await {
            let result = result.expect("Encryption task panicked")?;
            if let Some(request) = result.to_device_request {
                to_device_requests.push(request);
            }
            changes.sessions.extend(result.updated_olm_sessions);
            no_olm_devices.extend(result.no_olm_devices);
        }

        Ok((to_device_requests, no_olm_devices))
    }
}

/// Helper for [`GroupSessionManager::encrypt_content_for_devices`].
///
/// Encrypt the given content for the given devices and build a to-device
/// request to send the encrypted content to them.
///
/// See also [`GroupSessionManager::encrypt_session_for`], which is similar
/// but applies specifically to `m.room_key` messages that hold a megolm
/// session key.
async fn encrypt_content_for_devices(
    store: Arc<CryptoStoreWrapper>,
    event_type: String,
    content: impl Serialize + Clone + Send + 'static,
    devices: Vec<DeviceData>,
) -> OlmResult<EncryptForDevicesResult> {
    let mut result_builder = EncryptForDevicesResultBuilder::default();

    async fn encrypt(
        store: Arc<CryptoStoreWrapper>,
        device: DeviceData,
        event_type: String,
        bundle_data: impl Serialize,
    ) -> OlmResult<(Session, Raw<ToDeviceEncryptedEventContent>)> {
        device.encrypt(store.as_ref(), &event_type, bundle_data).await
    }

    let tasks = devices.iter().map(|device| {
        spawn(
            encrypt(store.clone(), device.clone(), event_type.clone(), content.clone())
                .in_current_span(),
        )
    });

    let results = join_all(tasks).await;

    for (device, result) in zip(devices, results) {
        let encryption_result = result.expect("Encryption task panicked");

        match encryption_result {
            Ok((used_session, message)) => {
                result_builder.on_successful_encryption(&device, used_session, message.cast());
            }
            Err(OlmError::MissingSession) => {
                // There is no established Olm session for this device
                result_builder.on_missing_session(device);
            }
            Err(e) => return Err(e),
        }
    }

    Ok(result_builder.into_result())
}

/// Result of [`GroupSessionManager::encrypt_session_for`] and
/// [`encrypt_content_for_devices`].
#[derive(Debug)]
struct EncryptForDevicesResult {
    /// The request to send the to-device messages containing the encrypted
    /// payload, if any devices were found.
    to_device_request: Option<ToDeviceRequest>,

    /// The devices which lack an Olm session and therefore need a withheld code
    no_olm_devices: Vec<(DeviceData, WithheldCode)>,

    /// The Olm sessions which were used to encrypt the requests and now need
    /// persisting to the store.
    updated_olm_sessions: Vec<Session>,
}

/// A helper for building [`EncryptForDevicesResult`]
#[derive(Debug, Default)]
struct EncryptForDevicesResultBuilder {
    /// The payloads of the to-device messages
    messages: BTreeMap<OwnedUserId, BTreeMap<DeviceIdOrAllDevices, Raw<AnyToDeviceEventContent>>>,

    /// The devices which lack an Olm session and therefore need a withheld code
    no_olm_devices: Vec<(DeviceData, WithheldCode)>,

    /// The Olm sessions which were used to encrypt the requests and now need
    /// persisting to the store.
    updated_olm_sessions: Vec<Session>,
}

impl EncryptForDevicesResultBuilder {
    /// Record a successful encryption. The encrypted message is added to the
    /// list to be sent, and the olm session is added to the list of those
    /// that have been modified.
    pub fn on_successful_encryption(
        &mut self,
        device: &DeviceData,
        used_session: Session,
        message: Raw<AnyToDeviceEventContent>,
    ) {
        self.updated_olm_sessions.push(used_session);

        self.messages
            .entry(device.user_id().to_owned())
            .or_default()
            .insert(DeviceIdOrAllDevices::DeviceId(device.device_id().to_owned()), message);
    }

    /// Record a device which didn't have an active Olm session.
    pub fn on_missing_session(&mut self, device: DeviceData) {
        self.no_olm_devices.push((device, WithheldCode::NoOlm));
    }

    /// Transform the accumulated results into an [`EncryptForDevicesResult`],
    /// wrapping the messages, if any, into a `ToDeviceRequest`.
    pub fn into_result(self) -> EncryptForDevicesResult {
        let EncryptForDevicesResultBuilder { updated_olm_sessions, no_olm_devices, messages } =
            self;

        let mut encrypt_for_devices_result = EncryptForDevicesResult {
            to_device_request: None,
            updated_olm_sessions,
            no_olm_devices,
        };

        if !messages.is_empty() {
            let request = ToDeviceRequest {
                event_type: ToDeviceEventType::RoomEncrypted,
                txn_id: TransactionId::new(),
                messages,
            };
            trace!(
                recipient_count = request.message_count(),
                transaction_id = ?request.txn_id,
                "Created a to-device request carrying room keys",
            );
            encrypt_for_devices_result.to_device_request = Some(request);
        };

        encrypt_for_devices_result
    }
}

fn recipient_list_to_users_and_devices(
    recipient_devices: &[DeviceData],
) -> BTreeMap<&UserId, BTreeSet<&DeviceId>> {
    #[allow(unknown_lints, clippy::unwrap_or_default)] // false positive
    recipient_devices.iter().fold(BTreeMap::new(), |mut acc, d| {
        acc.entry(d.user_id()).or_insert_with(BTreeSet::new).insert(d.device_id());
        acc
    })
}

#[cfg(test)]
mod tests {
    use std::{
        collections::{BTreeMap, BTreeSet},
        iter,
        ops::Deref,
        sync::Arc,
    };

    use assert_matches2::assert_let;
    use matrix_sdk_common::deserialized_responses::WithheldCode;
    use matrix_sdk_test::{async_test, ruma_response_from_json};
    use ruma::{
        api::client::{
            keys::{claim_keys, get_keys, upload_keys},
            to_device::send_event_to_device::v3::Response as ToDeviceResponse,
        },
        device_id,
        events::room::{
            history_visibility::HistoryVisibility, EncryptedFileInit, JsonWebKey, JsonWebKeyInit,
        },
        owned_room_id, room_id,
        serde::Base64,
        to_device::DeviceIdOrAllDevices,
        user_id, DeviceId, OneTimeKeyAlgorithm, OwnedMxcUri, TransactionId, UInt, UserId,
    };
    use serde_json::{json, Value};

    use crate::{
        identities::DeviceData,
        machine::{
            test_helpers::get_machine_pair_with_setup_sessions_test_helper, EncryptionSyncChanges,
        },
        olm::{Account, SenderData},
        session_manager::{group_sessions::CollectRecipientsResult, CollectStrategy},
        types::{
            events::{
                room::encrypted::EncryptedToDeviceEvent,
                room_key_bundle::RoomKeyBundleContent,
                room_key_withheld::RoomKeyWithheldContent::{self, MegolmV1AesSha2},
            },
            requests::ToDeviceRequest,
            DeviceKeys, EventEncryptionAlgorithm, ProcessedToDeviceEvent,
        },
        EncryptionSettings, LocalTrust, OlmMachine,
    };

    fn alice_id() -> &'static UserId {
        user_id!("@alice:example.org")
    }

    fn alice_device_id() -> &'static DeviceId {
        device_id!("JLAFKJWSCS")
    }

    /// Returns a /keys/query response for user "@example:localhost"
    fn keys_query_response() -> get_keys::v3::Response {
        let data = include_bytes!("../../../../../benchmarks/benches/crypto_bench/keys_query.json");
        let data: Value = serde_json::from_slice(data).unwrap();
        ruma_response_from_json(&data)
    }

    fn bob_keys_query_response() -> get_keys::v3::Response {
        let data = json!({
            "device_keys": {
                "@bob:localhost": {
                    "BOBDEVICE": {
                        "user_id": "@bob:localhost",
                        "device_id": "BOBDEVICE",
                        "algorithms": [
                            "m.olm.v1.curve25519-aes-sha2",
                            "m.megolm.v1.aes-sha2",
                            "m.megolm.v2.aes-sha2"
                        ],
                        "keys": {
                            "curve25519:BOBDEVICE": "QzXDFZj0Pt5xG4r11XGSrqE4mnFOTgRM5pz7n3tzohU",
                            "ed25519:BOBDEVICE": "T7QMEXcEo/NfiC/8doVHT+2XnMm0pDpRa27bmE8PlPI"
                        },
                        "signatures": {
                            "@bob:localhost": {
                                "ed25519:BOBDEVICE": "1Ee9J02KoVf4DKhT+LkurpZJEygiznqpgkT4lqvMTLtZyzShsVTnwmoMPttuGcJkLp9lMK1egveNYCEaYP80Cw"
                            }
                        }
                    }
                }
            }
        });
        ruma_response_from_json(&data)
    }

    /// Returns a keys claim response for device `BOBDEVICE` of user
    /// `@bob:localhost`.
    fn bob_one_time_key() -> claim_keys::v3::Response {
        let data = json!({
            "failures": {},
            "one_time_keys":{
                "@bob:localhost":{
                    "BOBDEVICE":{
                      "signed_curve25519:AAAAAAAAAAA": {
                          "key":"bm1olfbksjC5SwKxCLLK4XaINCA0FwR/155J85gIpCk",
                          "signatures":{
                              "@bob:localhost":{
                                  "ed25519:BOBDEVICE":"BKyS/+EV76zdZkWgny2D0svZ0ycS3etfyHCrsDgm7MYe166HqQmSoX29HsjGLvE/5F+Sg2zW7RJileUvquPwDA"
                              }
                          }
                      }
                    }
                }
            }
        });
        ruma_response_from_json(&data)
    }

    /// Returns a key claim response for device `NMMBNBUSNR` of user
    /// `@example2:localhost`
    fn keys_claim_response() -> claim_keys::v3::Response {
        let data = include_bytes!("../../../../../benchmarks/benches/crypto_bench/keys_claim.json");
        let data: Value = serde_json::from_slice(data).unwrap();
        ruma_response_from_json(&data)
    }

    async fn machine_with_user_test_helper(user_id: &UserId, device_id: &DeviceId) -> OlmMachine {
        let keys_query = keys_query_response();
        let txn_id = TransactionId::new();

        let machine = OlmMachine::new(user_id, device_id).await;

        // complete a /keys/query and /keys/claim for @example:localhost
        machine.mark_request_as_sent(&txn_id, &keys_query).await.unwrap();
        let (txn_id, _keys_claim_request) = machine
            .get_missing_sessions(iter::once(user_id!("@example:localhost")))
            .await
            .unwrap()
            .unwrap();
        let keys_claim = keys_claim_response();
        machine.mark_request_as_sent(&txn_id, &keys_claim).await.unwrap();

        // complete a /keys/query and /keys/claim for @bob:localhost
        machine.mark_request_as_sent(&txn_id, &bob_keys_query_response()).await.unwrap();
        let (txn_id, _keys_claim_request) = machine
            .get_missing_sessions(iter::once(user_id!("@bob:localhost")))
            .await
            .unwrap()
            .unwrap();
        machine.mark_request_as_sent(&txn_id, &bob_one_time_key()).await.unwrap();

        machine
    }

    async fn machine() -> OlmMachine {
        machine_with_user_test_helper(alice_id(), alice_device_id()).await
    }

    async fn machine_with_shared_room_key_test_helper() -> OlmMachine {
        let machine = machine().await;
        let room_id = room_id!("!test:localhost");
        let keys_claim = keys_claim_response();

        let users = keys_claim.one_time_keys.keys().map(Deref::deref);
        let requests =
            machine.share_room_key(room_id, users, EncryptionSettings::default()).await.unwrap();

        let outbound =
            machine.inner.group_session_manager.get_outbound_group_session(room_id).unwrap();

        assert!(!outbound.pending_requests().is_empty());
        assert!(!outbound.shared());

        let response = ToDeviceResponse::new();
        for request in requests {
            machine.mark_request_as_sent(&request.txn_id, &response).await.unwrap();
        }

        assert!(outbound.shared());
        assert!(outbound.pending_requests().is_empty());

        machine
    }

    #[async_test]
    async fn test_sharing() {
        let machine = machine().await;
        let room_id = room_id!("!test:localhost");
        let keys_claim = keys_claim_response();

        let users = keys_claim.one_time_keys.keys().map(Deref::deref);

        let requests =
            machine.share_room_key(room_id, users, EncryptionSettings::default()).await.unwrap();

        let event_count: usize = requests
            .iter()
            .filter(|r| r.event_type == "m.room.encrypted".into())
            .map(|r| r.message_count())
            .sum();

        // The keys claim response has a couple of one-time keys with invalid
        // signatures, thus only 148 sessions are actually created, we check
        // that all 148 valid sessions get an room key.
        assert_eq!(event_count, 148);

        let withheld_count: usize = requests
            .iter()
            .filter(|r| r.event_type == "m.room_key.withheld".into())
            .map(|r| r.message_count())
            .sum();
        assert_eq!(withheld_count, 2);
    }

    fn count_withheld_from(requests: &[Arc<ToDeviceRequest>], code: WithheldCode) -> usize {
        requests
            .iter()
            .filter(|r| r.event_type == "m.room_key.withheld".into())
            .map(|r| {
                let mut count = 0;
                // count targets
                for message in r.messages.values() {
                    message.iter().for_each(|(_, content)| {
                        let withheld: RoomKeyWithheldContent =
                            content.deserialize_as::<RoomKeyWithheldContent>().unwrap();

                        if let MegolmV1AesSha2(content) = withheld {
                            if content.withheld_code() == code {
                                count += 1;
                            }
                        }
                    })
                }
                count
            })
            .sum()
    }

    #[async_test]
    async fn test_no_olm_sent_once() {
        let machine = machine().await;
        let keys_claim = keys_claim_response();

        let users = keys_claim.one_time_keys.keys().map(Deref::deref);

        let first_room_id = room_id!("!test:localhost");

        let requests = machine
            .share_room_key(first_room_id, users.to_owned(), EncryptionSettings::default())
            .await
            .unwrap();

        // there will be two no_olm
        let withheld_count: usize = count_withheld_from(&requests, WithheldCode::NoOlm);
        assert_eq!(withheld_count, 2);

        // Re-sharing same session while request has not been sent should not produces
        // withheld
        let new_requests = machine
            .share_room_key(first_room_id, users, EncryptionSettings::default())
            .await
            .unwrap();
        let withheld_count: usize = count_withheld_from(&new_requests, WithheldCode::NoOlm);
        // No additional request was added, still the 2 already pending
        assert_eq!(withheld_count, 2);

        let response = ToDeviceResponse::new();
        for request in requests {
            machine.mark_request_as_sent(&request.txn_id, &response).await.unwrap();
        }

        // The fact that an olm was sent should be remembered even if sharing another
        // session in an other room.
        let second_room_id = room_id!("!other:localhost");
        let users = keys_claim.one_time_keys.keys().map(Deref::deref);
        let requests = machine
            .share_room_key(second_room_id, users, EncryptionSettings::default())
            .await
            .unwrap();

        let withheld_count: usize = count_withheld_from(&requests, WithheldCode::NoOlm);
        assert_eq!(withheld_count, 0);

        // Help how do I simulate the creation of a new session for the device
        // with no session now?
    }

    #[async_test]
    async fn test_ratcheted_sharing() {
        let machine = machine_with_shared_room_key_test_helper().await;

        let room_id = room_id!("!test:localhost");
        let late_joiner = user_id!("@bob:localhost");
        let keys_claim = keys_claim_response();

        let mut users: BTreeSet<_> = keys_claim.one_time_keys.keys().map(Deref::deref).collect();
        users.insert(late_joiner);

        let requests = machine
            .share_room_key(room_id, users.into_iter(), EncryptionSettings::default())
            .await
            .unwrap();

        let event_count: usize = requests
            .iter()
            .filter(|r| r.event_type == "m.room.encrypted".into())
            .map(|r| r.message_count())
            .sum();
        let outbound =
            machine.inner.group_session_manager.get_outbound_group_session(room_id).unwrap();

        assert_eq!(event_count, 1);
        assert!(!outbound.pending_requests().is_empty());
    }

    #[async_test]
    async fn test_changing_encryption_settings() {
        let machine = machine_with_shared_room_key_test_helper().await;
        let room_id = room_id!("!test:localhost");
        let keys_claim = keys_claim_response();

        let users = keys_claim.one_time_keys.keys().map(Deref::deref);
        let outbound =
            machine.inner.group_session_manager.get_outbound_group_session(room_id).unwrap();

        let CollectRecipientsResult { should_rotate, .. } = machine
            .inner
            .group_session_manager
            .collect_session_recipients(users.clone(), &EncryptionSettings::default(), &outbound)
            .await
            .unwrap();

        assert!(!should_rotate);

        let settings = EncryptionSettings {
            history_visibility: HistoryVisibility::Invited,
            ..Default::default()
        };

        let CollectRecipientsResult { should_rotate, .. } = machine
            .inner
            .group_session_manager
            .collect_session_recipients(users.clone(), &settings, &outbound)
            .await
            .unwrap();

        assert!(should_rotate);

        let settings = EncryptionSettings {
            algorithm: EventEncryptionAlgorithm::from("m.megolm.v2.aes-sha2"),
            ..Default::default()
        };

        let CollectRecipientsResult { should_rotate, .. } = machine
            .inner
            .group_session_manager
            .collect_session_recipients(users, &settings, &outbound)
            .await
            .unwrap();

        assert!(should_rotate);
    }

    #[async_test]
    async fn test_key_recipient_collecting() {
        // The user id comes from the fact that the keys_query.json file uses
        // this one.
        let user_id = user_id!("@example:localhost");
        let device_id = device_id!("TESTDEVICE");
        let room_id = room_id!("!test:localhost");

        let machine = machine_with_user_test_helper(user_id, device_id).await;

        let (outbound, _) = machine
            .inner
            .group_session_manager
            .get_or_create_outbound_session(
                room_id,
                EncryptionSettings::default(),
                SenderData::unknown(),
            )
            .await
            .expect("We should be able to create a new session");
        let history_visibility = HistoryVisibility::Joined;
        let settings = EncryptionSettings { history_visibility, ..Default::default() };

        let users = [user_id].into_iter();

        let CollectRecipientsResult { devices: recipients, .. } = machine
            .inner
            .group_session_manager
            .collect_session_recipients(users, &settings, &outbound)
            .await
            .expect("We should be able to collect the session recipients");

        assert!(!recipients[user_id].is_empty());

        // Make sure that our own device isn't part of the recipients.
        assert!(!recipients[user_id]
            .iter()
            .any(|d| d.user_id() == user_id && d.device_id() == device_id));

        let settings = EncryptionSettings {
            sharing_strategy: CollectStrategy::OnlyTrustedDevices,
            ..Default::default()
        };
        let users = [user_id].into_iter();

        let CollectRecipientsResult { devices: recipients, .. } = machine
            .inner
            .group_session_manager
            .collect_session_recipients(users, &settings, &outbound)
            .await
            .expect("We should be able to collect the session recipients");

        assert!(recipients[user_id].is_empty());

        let device_id = "AFGUOBTZWM".into();
        let device = machine.get_device(user_id, device_id, None).await.unwrap().unwrap();
        device.set_local_trust(LocalTrust::Verified).await.unwrap();
        let users = [user_id].into_iter();

        let CollectRecipientsResult { devices: recipients, withheld_devices: withheld, .. } =
            machine
                .inner
                .group_session_manager
                .collect_session_recipients(users, &settings, &outbound)
                .await
                .expect("We should be able to collect the session recipients");

        assert!(recipients[user_id]
            .iter()
            .any(|d| d.user_id() == user_id && d.device_id() == device_id));

        let devices = machine.get_user_devices(user_id, None).await.unwrap();
        devices
            .devices()
            // Ignore our own device
            .filter(|d| d.device_id() != device_id!("TESTDEVICE"))
            .for_each(|d| {
                if d.is_blacklisted() {
                    assert!(withheld.iter().any(|(dev, w)| {
                        dev.device_id() == d.device_id() && w == &WithheldCode::Blacklisted
                    }));
                } else if !d.is_verified() {
                    // the device should then be in the list of withhelds
                    assert!(withheld.iter().any(|(dev, w)| {
                        dev.device_id() == d.device_id() && w == &WithheldCode::Unverified
                    }));
                }
            });

        assert_eq!(149, withheld.len());
    }

    #[async_test]
    async fn test_sharing_withheld_only_trusted() {
        let machine = machine().await;
        let room_id = room_id!("!test:localhost");
        let keys_claim = keys_claim_response();

        let users = keys_claim.one_time_keys.keys().map(Deref::deref);
        let settings = EncryptionSettings {
            sharing_strategy: CollectStrategy::OnlyTrustedDevices,
            ..Default::default()
        };

        // Trust only one
        let user_id = user_id!("@example:localhost");
        let device_id = "MWFXPINOAO".into();
        let device = machine.get_device(user_id, device_id, None).await.unwrap().unwrap();
        device.set_local_trust(LocalTrust::Verified).await.unwrap();
        machine
            .get_device(user_id, "MWVTUXDNNM".into(), None)
            .await
            .unwrap()
            .unwrap()
            .set_local_trust(LocalTrust::BlackListed)
            .await
            .unwrap();

        let requests = machine.share_room_key(room_id, users, settings).await.unwrap();

        // One room key should be sent
        let room_key_count =
            requests.iter().filter(|r| r.event_type == "m.room.encrypted".into()).count();

        assert_eq!(1, room_key_count);

        let withheld_count =
            requests.iter().filter(|r| r.event_type == "m.room_key.withheld".into()).count();
        // Can be send in one batch
        assert_eq!(1, withheld_count);

        let event_count: usize = requests
            .iter()
            .filter(|r| r.event_type == "m.room_key.withheld".into())
            .map(|r| r.message_count())
            .sum();

        // withhelds are sent in clear so all device should be counted (even if no OTK)
        assert_eq!(event_count, 149);

        // One should be blacklisted
        let has_blacklist =
            requests.iter().filter(|r| r.event_type == "m.room_key.withheld".into()).any(|r| {
                let device_key = DeviceIdOrAllDevices::from(device_id!("MWVTUXDNNM").to_owned());
                let content = &r.messages[user_id][&device_key];
                let withheld: RoomKeyWithheldContent =
                    content.deserialize_as::<RoomKeyWithheldContent>().unwrap();
                if let MegolmV1AesSha2(content) = withheld {
                    content.withheld_code() == WithheldCode::Blacklisted
                } else {
                    false
                }
            });

        assert!(has_blacklist);
    }

    #[async_test]
    async fn test_no_olm_withheld_only_sent_once() {
        let keys_query = keys_query_response();
        let txn_id = TransactionId::new();

        let machine = OlmMachine::new(alice_id(), alice_device_id()).await;

        machine.mark_request_as_sent(&txn_id, &keys_query).await.unwrap();
        machine.mark_request_as_sent(&txn_id, &bob_keys_query_response()).await.unwrap();

        let first_room = room_id!("!test:localhost");
        let second_room = room_id!("!test2:localhost");
        let bob_id = user_id!("@bob:localhost");

        let settings = EncryptionSettings::default();
        let users = [bob_id];

        let requests = machine
            .share_room_key(first_room, users.into_iter(), settings.to_owned())
            .await
            .unwrap();

        // One withheld request should be sent.
        let withheld_count =
            requests.iter().filter(|r| r.event_type == "m.room_key.withheld".into()).count();

        assert_eq!(withheld_count, 1);
        assert_eq!(requests.len(), 1);

        // On the second room key share attempt we're not sending another `m.no_olm`
        // code since the first one is taking care of this.
        let second_requests =
            machine.share_room_key(second_room, users.into_iter(), settings).await.unwrap();

        let withheld_count =
            second_requests.iter().filter(|r| r.event_type == "m.room_key.withheld".into()).count();

        assert_eq!(withheld_count, 0);
        assert_eq!(second_requests.len(), 0);

        let response = ToDeviceResponse::new();

        let device = machine.get_device(bob_id, "BOBDEVICE".into(), None).await.unwrap().unwrap();

        // The device should be marked as having the `m.no_olm` code received only after
        // the request has been marked as sent.
        assert!(!device.was_withheld_code_sent());

        for request in requests {
            machine.mark_request_as_sent(&request.txn_id, &response).await.unwrap();
        }

        let device = machine.get_device(bob_id, "BOBDEVICE".into(), None).await.unwrap().unwrap();

        assert!(device.was_withheld_code_sent());
    }

    #[async_test]
    async fn test_resend_session_after_unwedging() {
        let machine = OlmMachine::new(alice_id(), alice_device_id()).await;
        assert_let!(Ok(Some((txn_id, device_keys_request))) = machine.upload_device_keys().await);
        let device_keys_response = upload_keys::v3::Response::new(BTreeMap::from([(
            OneTimeKeyAlgorithm::SignedCurve25519,
            UInt::new(device_keys_request.one_time_keys.len() as u64).unwrap(),
        )]));
        machine.mark_request_as_sent(&txn_id, &device_keys_response).await.unwrap();

        let room_id = room_id!("!test:localhost");

        let bob_id = user_id!("@bob:localhost");
        let bob_account = Account::new(bob_id);
        let keys_query_data = json!({
            "device_keys": {
                "@bob:localhost": {
                    bob_account.device_id.clone(): bob_account.device_keys()
                }
            }
        });
        let keys_query: get_keys::v3::Response = ruma_response_from_json(&keys_query_data);
        let txn_id = TransactionId::new();
        machine.mark_request_as_sent(&txn_id, &keys_query).await.unwrap();

        let alice_device_keys =
            device_keys_request.device_keys.unwrap().deserialize_as::<DeviceKeys>().unwrap();
        let mut alice_otks = device_keys_request.one_time_keys.iter();
        let alice_device = DeviceData::new(alice_device_keys, LocalTrust::Unset);

        {
            // Bob creates an Olm session with Alice and encrypts a message to her
            let (alice_otk_id, alice_otk) = alice_otks.next().unwrap();
            let mut session = bob_account
                .create_outbound_session(
                    &alice_device,
                    &BTreeMap::from([(alice_otk_id.clone(), alice_otk.clone())]),
                    bob_account.device_keys(),
                )
                .unwrap();
            let content = session.encrypt(&alice_device, "m.dummy", json!({}), None).await.unwrap();

            let to_device =
                EncryptedToDeviceEvent::new(bob_id.to_owned(), content.deserialize().unwrap());

            // Alice decrypts the message
            let sync_changes = EncryptionSyncChanges {
                to_device_events: vec![crate::utilities::json_convert(&to_device).unwrap()],
                changed_devices: &Default::default(),
                one_time_keys_counts: &Default::default(),
                unused_fallback_keys: None,
                next_batch_token: None,
            };
            let (decrypted, _) = machine.receive_sync_changes(sync_changes).await.unwrap();

            assert_eq!(1, decrypted.len());
        }

        // Alice shares the room key with Bob
        {
            let requests = machine
                .share_room_key(room_id, [bob_id].into_iter(), EncryptionSettings::default())
                .await
                .unwrap();

            // We should have had one to-device event
            let event_count: usize = requests
                .iter()
                .filter(|r| r.event_type == "m.room.encrypted".into())
                .map(|r| r.message_count())
                .sum();
            assert_eq!(event_count, 1);

            let response = ToDeviceResponse::new();
            for request in requests {
                machine.mark_request_as_sent(&request.txn_id, &response).await.unwrap();
            }
        }

        // When Alice shares the room key again, there shouldn't be any
        // to-device events, since we already shared with Bob
        {
            let requests = machine
                .share_room_key(room_id, [bob_id].into_iter(), EncryptionSettings::default())
                .await
                .unwrap();

            let event_count: usize = requests
                .iter()
                .filter(|r| r.event_type == "m.room.encrypted".into())
                .map(|r| r.message_count())
                .sum();
            assert_eq!(event_count, 0);
        }

        // Pretend that Bob wasn't able to decrypt, so he tries to unwedge
        {
            let (alice_otk_id, alice_otk) = alice_otks.next().unwrap();
            let mut session = bob_account
                .create_outbound_session(
                    &alice_device,
                    &BTreeMap::from([(alice_otk_id.clone(), alice_otk.clone())]),
                    bob_account.device_keys(),
                )
                .unwrap();
            let content = session.encrypt(&alice_device, "m.dummy", json!({}), None).await.unwrap();

            let to_device =
                EncryptedToDeviceEvent::new(bob_id.to_owned(), content.deserialize().unwrap());

            // Alice decrypts the unwedge message
            let sync_changes = EncryptionSyncChanges {
                to_device_events: vec![crate::utilities::json_convert(&to_device).unwrap()],
                changed_devices: &Default::default(),
                one_time_keys_counts: &Default::default(),
                unused_fallback_keys: None,
                next_batch_token: None,
            };
            let (decrypted, _) = machine.receive_sync_changes(sync_changes).await.unwrap();

            assert_eq!(1, decrypted.len());
        }

        // When Alice shares the room key again, it should be re-shared with Bob
        {
            let requests = machine
                .share_room_key(room_id, [bob_id].into_iter(), EncryptionSettings::default())
                .await
                .unwrap();

            let event_count: usize = requests
                .iter()
                .filter(|r| r.event_type == "m.room.encrypted".into())
                .map(|r| r.message_count())
                .sum();
            assert_eq!(event_count, 1);

            let response = ToDeviceResponse::new();
            for request in requests {
                machine.mark_request_as_sent(&request.txn_id, &response).await.unwrap();
            }
        }

        // When Alice shares the room key yet again, there shouldn't be any
        // to-device events
        {
            let requests = machine
                .share_room_key(room_id, [bob_id].into_iter(), EncryptionSettings::default())
                .await
                .unwrap();

            let event_count: usize = requests
                .iter()
                .filter(|r| r.event_type == "m.room.encrypted".into())
                .map(|r| r.message_count())
                .sum();
            assert_eq!(event_count, 0);
        }
    }

    #[async_test]
    async fn test_room_key_bundle_sharing() {
        let (alice, bob) = get_machine_pair_with_setup_sessions_test_helper(
            user_id!("@alice:localhost"),
            user_id!("@bob:localhost"),
            false,
        )
        .await;

        // Alice trusts Bob's device
        let device = alice.get_device(bob.user_id(), bob.device_id(), None).await.unwrap().unwrap();
        device.set_local_trust(LocalTrust::Verified).await.unwrap();

        let content = RoomKeyBundleContent {
            room_id: owned_room_id!("!room:id"),
            file: (EncryptedFileInit {
                url: OwnedMxcUri::from("test"),
                key: JsonWebKey::from(JsonWebKeyInit {
                    kty: "oct".to_owned(),
                    key_ops: vec!["encrypt".to_owned(), "decrypt".to_owned()],
                    alg: "A256CTR".to_owned(),
                    #[allow(clippy::unnecessary_to_owned)]
                    k: Base64::new(vec![0u8; 0]),
                    ext: true,
                }),
                iv: Base64::new(vec![0u8; 0]),
                hashes: Default::default(),
                v: "".to_owned(),
            })
            .into(),
        };

        let requests = alice
            .share_room_key_bundle_data(
                bob.user_id(),
                &CollectStrategy::OnlyTrustedDevices,
                content,
            )
            .await
            .unwrap();

        // There should be exactly one message
        let requests: Vec<_> =
            requests.iter().filter(|r| r.event_type == "m.room.encrypted".into()).collect();
        let message_count: usize = requests.iter().map(|r| r.message_count()).sum();
        assert_eq!(message_count, 1);

        // Bob decrypts the message
        let bob_message = requests[0]
            .messages
            .get(bob.user_id())
            .unwrap()
            .get(&(bob.device_id().to_owned().into()))
            .unwrap();
        let to_device = EncryptedToDeviceEvent::new(
            alice.user_id().to_owned(),
            bob_message.cast_ref().deserialize().unwrap(),
        );

        let sync_changes = EncryptionSyncChanges {
            to_device_events: vec![crate::utilities::json_convert(&to_device).unwrap()],
            changed_devices: &Default::default(),
            one_time_keys_counts: &Default::default(),
            unused_fallback_keys: None,
            next_batch_token: None,
        };
        let (decrypted, _) = bob.receive_sync_changes(sync_changes).await.unwrap();
        assert_eq!(1, decrypted.len());
        use crate::types::events::EventType;
        assert_let!(
            ProcessedToDeviceEvent::Decrypted { raw, .. } = decrypted.first().unwrap().clone()
        );
        assert_eq!(
            raw.get_field::<String>("type").unwrap().unwrap(),
            RoomKeyBundleContent::EVENT_TYPE,
        );
    }
}
