whatsapp-rust 0.5.0

use crate::client::Client;
use crate::store::signal_adapter::SignalProtocolStoreAdapter;
use anyhow::anyhow;
use wacore::client::context::SendContextResolver;
use wacore::libsignal::protocol::SignalProtocolError;
use wacore::types::jid::JidExt;
use wacore::types::message::AddressingMode;
use wacore_binary::jid::{DeviceKey, Jid, JidExt as _};
use wacore_binary::node::Node;
use waproto::whatsapp as wa;

/// Options for sending messages with additional customization.
#[derive(Debug, Clone, Default)]
pub struct SendOptions {
    /// Extra XML nodes to add to the message stanza.
    pub extra_stanza_nodes: Vec<Node>,
}

/// Specifies who is revoking (deleting) the message.
#[derive(Debug, Clone, PartialEq, Eq, Default)]
pub enum RevokeType {
    /// The message sender deleting their own message.
    #[default]
    Sender,
    /// A group admin deleting another user's message.
    /// `original_sender` is the JID of the user who sent the message being deleted.
    Admin { original_sender: Jid },
}

impl Client {
    /// Send an end-to-end encrypted message to a user or group.
    ///
    /// Returns the message ID on success. For status/story updates use
    /// [`Client::status()`] instead.
    pub async fn send_message(
        &self,
        to: Jid,
        message: wa::Message,
    ) -> Result<String, anyhow::Error> {
        self.send_message_with_options(to, message, SendOptions::default())
            .await
    }

    /// Send a message with additional options.
    pub async fn send_message_with_options(
        &self,
        to: Jid,
        message: wa::Message,
        options: SendOptions,
    ) -> Result<String, anyhow::Error> {
        let request_id = self.generate_message_id().await;
        self.send_message_impl(
            to,
            &message,
            Some(request_id.clone()),
            false,
            false,
            None,
            options.extra_stanza_nodes,
        )
        .await?;
        Ok(request_id)
    }

    /// Send a status/story update to the given recipients using sender key encryption.
    ///
    /// This builds a `GroupInfo` from the provided recipients (always PN addressing mode),
    /// then reuses the group encryption pipeline with `to = status@broadcast`.
    pub(crate) async fn send_status_message(
        &self,
        message: wa::Message,
        recipients: Vec<Jid>,
        options: crate::features::status::StatusSendOptions,
    ) -> Result<String, anyhow::Error> {
        use wacore::client::context::GroupInfo;
        use wacore_binary::builder::NodeBuilder;

        if recipients.is_empty() {
            return Err(anyhow!("Cannot send status with no recipients"));
        }

        let to = Jid::status_broadcast();
        let request_id = self.generate_message_id().await;

        let device_snapshot = self.persistence_manager.get_device_snapshot().await;
        let own_jid = device_snapshot
            .pn
            .clone()
            .ok_or_else(|| anyhow::Error::from(crate::client::ClientError::NotLoggedIn))?;
        // Status always uses PN addressing, so own_lid is only needed as a
        // fallback parameter for prepare_group_stanza (unused in PN mode).
        let own_lid = device_snapshot
            .lid
            .clone()
            .unwrap_or_else(|| own_jid.clone());
        let account_info = device_snapshot.account.clone();

        // Status always uses PN addressing. Resolve any LID recipients to their
        // phone numbers so we don't end up with duplicate PN+LID entries for the
        // same user (which causes server error 400).
        // Reject non-user JIDs (groups, broadcasts, etc.) to prevent invalid
        // <participants> entries that cause server errors.
        let mut resolved_recipients = Vec::with_capacity(recipients.len());
        for jid in recipients {
            if jid.is_group() || jid.is_status_broadcast() || jid.is_broadcast_list() {
                return Err(anyhow!(
                    "Invalid status recipient {}: must be a user JID, not a group/broadcast",
                    jid
                ));
            }
            if jid.is_lid() {
                if let Some(pn) = self.lid_pn_cache.get_phone_number(&jid.user).await {
                    resolved_recipients
                        .push(Jid::new(&pn, wacore_binary::jid::DEFAULT_USER_SERVER));
                } else {
                    return Err(anyhow!(
                        "No PN mapping for LID {}. Ensure the recipient has been \
                         contacted previously.",
                        jid
                    ));
                }
            } else {
                resolved_recipients.push(jid);
            }
        }

        if resolved_recipients.is_empty() {
            return Err(anyhow!("No valid PN recipients after LID resolution"));
        }

        // Deduplicate by user (in case both LID and PN were provided for the same user)
        let mut seen_users = std::collections::HashSet::new();
        resolved_recipients.retain(|jid| seen_users.insert(jid.user.clone()));

        let mut group_info = GroupInfo::new(resolved_recipients, AddressingMode::Pn);

        // Ensure we're in the participant list
        let own_base = own_jid.to_non_ad();
        if !group_info
            .participants
            .iter()
            .any(|p| p.is_same_user_as(&own_base))
        {
            group_info.participants.push(own_base);
        }

        self.add_recent_message(to.clone(), request_id.clone(), &message)
            .await;

        let device_store_arc = self.persistence_manager.get_device_arc().await;
        let to_str = to.to_string();

        let force_skdm = {
            use wacore::libsignal::store::sender_key_name::SenderKeyName;
            let sender_address = own_jid.to_protocol_address();
            let sender_key_name = SenderKeyName::new(to_str.clone(), sender_address.to_string());

            let device_guard = device_store_arc.read().await;
            let key_exists = self
                .signal_cache
                .get_sender_key(&sender_key_name, &*device_guard.backend)
                .await?
                .is_some();

            !key_exists
        };

        let mut store_adapter =
            SignalProtocolStoreAdapter::new(device_store_arc.clone(), self.signal_cache.clone());
        let mut stores = wacore::send::SignalStores {
            session_store: &mut store_adapter.session_store,
            identity_store: &mut store_adapter.identity_store,
            prekey_store: &mut store_adapter.pre_key_store,
            signed_prekey_store: &store_adapter.signed_pre_key_store,
            sender_key_store: &mut store_adapter.sender_key_store,
        };

        let marked_for_fresh_skdm = self.consume_forget_marks(&to_str).await.unwrap_or_default();

        let skdm_target_devices: Option<Vec<Jid>> = if force_skdm {
            None
        } else {
            let known_recipients = self
                .persistence_manager
                .get_skdm_recipients(&to_str)
                .await
                .unwrap_or_default();

            if known_recipients.is_empty() {
                None
            } else {
                let jids_to_resolve: Vec<Jid> = group_info
                    .participants
                    .iter()
                    .map(|jid| jid.to_non_ad())
                    .collect();

                match SendContextResolver::resolve_devices(self, &jids_to_resolve).await {
                    Ok(all_devices) => {
                        let known_set: std::collections::HashSet<DeviceKey<'_>> =
                            known_recipients.iter().map(|j| j.device_key()).collect();
                        let new_devices: Vec<Jid> = all_devices
                            .into_iter()
                            .filter(|device| !known_set.contains(&device.device_key()))
                            .collect();
                        if new_devices.is_empty() {
                            Some(vec![])
                        } else {
                            Some(new_devices)
                        }
                    }
                    Err(e) => {
                        log::warn!("Failed to resolve devices for status SKDM check: {:?}", e);
                        None
                    }
                }
            }
        };

        let skdm_target_devices: Option<Vec<Jid>> = if !marked_for_fresh_skdm.is_empty() {
            match skdm_target_devices {
                None => None,
                Some(mut devices) => {
                    for marked_jid_str in &marked_for_fresh_skdm {
                        if let Ok(marked_jid) = marked_jid_str.parse::<Jid>()
                            && !devices.iter().any(|d| d.device_eq(&marked_jid))
                        {
                            devices.push(marked_jid);
                        }
                    }
                    Some(devices)
                }
            }
        } else {
            skdm_target_devices
        };

        let is_full_distribution = force_skdm || skdm_target_devices.is_none();
        let devices_receiving_skdm: Vec<Jid> = skdm_target_devices.clone().unwrap_or_default();
        #[allow(clippy::needless_late_init)]
        let skdm_is_full: bool;

        // WhatsApp Web includes <meta status_setting="..."/> on non-revoke status messages.
        // Revoke messages omit this node.
        let is_revoke = message.protocol_message.as_ref().is_some_and(|pm| {
            pm.r#type == Some(wa::message::protocol_message::Type::Revoke as i32)
        });
        let extra_stanza_nodes = if is_revoke {
            vec![]
        } else {
            vec![
                NodeBuilder::new("meta")
                    .attr("status_setting", options.privacy.as_str())
                    .build(),
            ]
        };

        let stanza = match wacore::send::prepare_group_stanza(
            &mut stores,
            self,
            &mut group_info,
            &own_jid,
            &own_lid,
            account_info.as_ref(),
            to.clone(),
            &message,
            request_id.clone(),
            force_skdm,
            skdm_target_devices,
            None,
            &extra_stanza_nodes,
        )
        .await
        {
            Ok(stanza) => {
                skdm_is_full = is_full_distribution;
                stanza
            }
            Err(e) => {
                if let Some(SignalProtocolError::NoSenderKeyState(_)) =
                    e.downcast_ref::<SignalProtocolError>()
                {
                    log::warn!("No sender key for status broadcast, forcing distribution.");

                    if let Err(e) = self
                        .persistence_manager
                        .clear_skdm_recipients(&to_str)
                        .await
                    {
                        log::warn!("Failed to clear status SKDM recipients: {:?}", e);
                    }

                    let mut store_adapter_retry = SignalProtocolStoreAdapter::new(
                        device_store_arc.clone(),
                        self.signal_cache.clone(),
                    );
                    let mut stores_retry = wacore::send::SignalStores {
                        session_store: &mut store_adapter_retry.session_store,
                        identity_store: &mut store_adapter_retry.identity_store,
                        prekey_store: &mut store_adapter_retry.pre_key_store,
                        signed_prekey_store: &store_adapter_retry.signed_pre_key_store,
                        sender_key_store: &mut store_adapter_retry.sender_key_store,
                    };

                    let retry_stanza = wacore::send::prepare_group_stanza(
                        &mut stores_retry,
                        self,
                        &mut group_info,
                        &own_jid,
                        &own_lid,
                        account_info.as_ref(),
                        to.clone(),
                        &message,
                        request_id.clone(),
                        true,
                        None,
                        None,
                        &extra_stanza_nodes,
                    )
                    .await?;

                    // Retry is always full distribution (rotated sender key)
                    skdm_is_full = true;
                    retry_stanza
                } else {
                    return Err(e);
                }
            }
        };

        // For status broadcasts, the server doesn't know the recipient list
        // (unlike groups where the server has the member list). We must always
        // include a <participants> node so the server knows who to deliver to.
        // If prepare_group_stanza already added one (SKDM distribution), we
        // extend it with bare <to> entries for devices that already have the
        // sender key. If there's no <participants> node yet, we create one.
        let stanza = self.ensure_status_participants(stanza, &group_info).await?;

        self.send_node(stanza).await?;

        // Update SKDM recipient cache AFTER server ACK (matches WhatsApp Web behavior).
        // WA Web only calls markHasSenderKey() after the server confirms receipt.
        self.update_skdm_recipients(
            &to_str,
            &devices_receiving_skdm,
            skdm_is_full,
            &group_info.participants,
        )
        .await;

        // Flush cached Signal state to DB after encryption
        if let Err(e) = self.flush_signal_cache().await {
            log::error!("Failed to flush signal cache after send_status_message: {e:?}");
        }

        Ok(request_id)
    }

    /// Update SKDM recipient bookkeeping after a successful group/status send.
    ///
    /// Called AFTER `send_node()` succeeds to match WhatsApp Web behavior, which
    /// only marks devices as having the sender key after the server ACK.
    /// If specific devices received SKDM, record them. If this was a full distribution
    /// (all participants), resolve all devices and record them instead.
    async fn update_skdm_recipients(
        &self,
        to_str: &str,
        devices_receiving_skdm: &[Jid],
        is_full_distribution: bool,
        participants: &[Jid],
    ) {
        if !devices_receiving_skdm.is_empty() {
            if let Err(e) = self
                .persistence_manager
                .add_skdm_recipients(to_str, devices_receiving_skdm)
                .await
            {
                log::warn!("Failed to update SKDM recipients: {:?}", e);
            }
        } else if is_full_distribution {
            let jids_to_resolve: Vec<Jid> =
                participants.iter().map(|jid| jid.to_non_ad()).collect();
            match SendContextResolver::resolve_devices(self, &jids_to_resolve).await {
                Ok(all_devices) => {
                    if let Err(e) = self
                        .persistence_manager
                        .add_skdm_recipients(to_str, &all_devices)
                        .await
                    {
                        log::warn!("Failed to persist SKDM recipients: {:?}", e);
                    }
                }
                Err(e) => {
                    log::warn!("Failed to resolve devices for SKDM recipients: {:?}", e);
                }
            }
        }
    }

    /// Ensure the status stanza has a <participants> node listing all recipient
    /// user JIDs. WhatsApp Web's `participantList` uses bare USER JIDs (not
    /// device JIDs) — `<to jid="user@s.whatsapp.net"/>` — to tell the server
    /// which users should receive the skmsg. The SKDM distribution list
    /// (already in <participants>) uses device JIDs with <enc> children.
    async fn ensure_status_participants(
        &self,
        stanza: wacore_binary::Node,
        group_info: &wacore::client::context::GroupInfo,
    ) -> Result<wacore_binary::Node, anyhow::Error> {
        Ok(wacore::send::ensure_status_participants(stanza, group_info))
    }

    /// Delete a message for everyone in the chat (revoke).
    ///
    /// This sends a revoke protocol message that removes the message for all participants.
    /// The message will show as "This message was deleted" for recipients.
    ///
    /// # Arguments
    /// * `to` - The chat JID (DM or group)
    /// * `message_id` - The ID of the message to delete
    /// * `revoke_type` - Use `RevokeType::Sender` to delete your own message,
    ///   or `RevokeType::Admin { original_sender }` to delete another user's message as group admin
    pub async fn revoke_message(
        &self,
        to: Jid,
        message_id: impl Into<String>,
        revoke_type: RevokeType,
    ) -> Result<(), anyhow::Error> {
        let message_id = message_id.into();
        // Verify we're logged in
        self.get_pn()
            .await
            .ok_or_else(|| anyhow::Error::from(crate::client::ClientError::NotLoggedIn))?;

        let (from_me, participant, edit_attr) = match &revoke_type {
            RevokeType::Sender => {
                // For sender revoke, participant is NOT set (from_me=true identifies it)
                // This matches whatsmeow's BuildMessageKey behavior
                (
                    true,
                    None,
                    crate::types::message::EditAttribute::SenderRevoke,
                )
            }
            RevokeType::Admin { original_sender } => {
                // Admin revoke requires group context
                if !to.is_group() {
                    return Err(anyhow!("Admin revoke is only valid for group chats"));
                }
                // The protocolMessageKey.participant should match the original message's key exactly
                // Do NOT convert LID to PN - pass through unchanged like WhatsApp Web does
                let participant_str = original_sender.to_non_ad().to_string();
                log::debug!(
                    "Admin revoke: using participant {} for MessageKey",
                    participant_str
                );
                (
                    false,
                    Some(participant_str),
                    crate::types::message::EditAttribute::AdminRevoke,
                )
            }
        };

        let revoke_message = wa::Message {
            protocol_message: Some(Box::new(wa::message::ProtocolMessage {
                key: Some(wa::MessageKey {
                    remote_jid: Some(to.to_string()),
                    from_me: Some(from_me),
                    id: Some(message_id.clone()),
                    participant,
                }),
                r#type: Some(wa::message::protocol_message::Type::Revoke as i32),
                ..Default::default()
            })),
            ..Default::default()
        };

        // The revoke message stanza needs a NEW unique ID, not the message ID being revoked
        // The message_id being revoked is already in protocolMessage.key.id
        // Passing None generates a fresh stanza ID
        //
        // For admin revokes, force SKDM distribution to get the proper message structure
        // with phash, <participants>, and <device-identity> that WhatsApp Web uses
        let force_skdm = matches!(revoke_type, RevokeType::Admin { .. });
        self.send_message_impl(
            to,
            &revoke_message,
            None,
            false,
            force_skdm,
            Some(edit_attr),
            vec![],
        )
        .await
    }

    #[allow(clippy::too_many_arguments)]
    pub(crate) async fn send_message_impl(
        &self,
        to: Jid,
        message: &wa::Message,
        request_id_override: Option<String>,
        peer: bool,
        force_key_distribution: bool,
        edit: Option<crate::types::message::EditAttribute>,
        extra_stanza_nodes: Vec<Node>,
    ) -> Result<(), anyhow::Error> {
        // Status broadcasts must go through send_status_message() which provides recipients
        if to.is_status_broadcast() {
            return Err(anyhow!(
                "Use send_status_message() or client.status() API for status@broadcast"
            ));
        }

        // Generate request ID early (doesn't need lock)
        let request_id = match request_id_override {
            Some(id) => id,
            None => self.generate_message_id().await,
        };

        // SKDM update data — only populated for group sends, deferred until after send_node().
        // This matches WhatsApp Web which only calls markHasSenderKey() after server ACK.
        struct SkdmUpdate {
            to_str: String,
            devices: Vec<Jid>,
            is_full_distribution: bool,
            participants: Vec<Jid>,
        }
        let mut skdm_update: Option<SkdmUpdate> = None;

        let stanza_to_send: wacore_binary::Node = if peer && !to.is_group() {
            // Peer messages are only valid for individual users, not groups
            // Resolve encryption JID and acquire lock ONLY for encryption
            let encryption_jid = self.resolve_encryption_jid(&to).await;
            let signal_addr_str = encryption_jid.to_protocol_address_string();

            let session_mutex = self
                .session_locks
                .get_with_by_ref(&signal_addr_str, async {
                    std::sync::Arc::new(async_lock::Mutex::new(()))
                })
                .await;
            let _session_guard = session_mutex.lock().await;

            let device_store_arc = self.persistence_manager.get_device_arc().await;
            let mut store_adapter =
                SignalProtocolStoreAdapter::new(device_store_arc, self.signal_cache.clone());

            wacore::send::prepare_peer_stanza(
                &mut store_adapter.session_store,
                &mut store_adapter.identity_store,
                to,
                encryption_jid,
                message,
                request_id,
            )
            .await?
        } else if to.is_group() {
            // Group messages: No client-level lock needed.
            // Each participant device is encrypted separately with its own per-device lock
            // inside prepare_group_stanza, so we don't need to serialize entire group sends.

            // Preparation work (no lock needed)
            let mut group_info = self.groups().query_info(&to).await?;

            let device_snapshot = self.persistence_manager.get_device_snapshot().await;
            let own_jid = device_snapshot
                .pn
                .clone()
                .ok_or_else(|| anyhow::Error::from(crate::client::ClientError::NotLoggedIn))?;
            let own_lid = device_snapshot
                .lid
                .clone()
                .ok_or_else(|| anyhow!("LID not set, cannot send to group"))?;
            let account_info = device_snapshot.account.clone();

            // Store serialized message bytes for retry (lightweight)
            self.add_recent_message(to.clone(), request_id.clone(), message)
                .await;

            let device_store_arc = self.persistence_manager.get_device_arc().await;
            let to_str = to.to_string();

            let (own_sending_jid, _) = match group_info.addressing_mode {
                crate::types::message::AddressingMode::Lid => (own_lid.clone(), "lid"),
                crate::types::message::AddressingMode::Pn => (own_jid.clone(), "pn"),
            };

            if !group_info
                .participants
                .iter()
                .any(|participant| participant.is_same_user_as(&own_sending_jid))
            {
                group_info.participants.push(own_sending_jid.to_non_ad());
            }

            let force_skdm = {
                use wacore::libsignal::protocol::SenderKeyStore;
                use wacore::libsignal::store::sender_key_name::SenderKeyName;
                let mut device_guard = device_store_arc.write().await;
                let sender_address = own_sending_jid.to_protocol_address();
                let sender_key_name =
                    SenderKeyName::new(to_str.clone(), sender_address.to_string());

                let key_exists = device_guard
                    .load_sender_key(&sender_key_name)
                    .await?
                    .is_some();

                force_key_distribution || !key_exists
            };

            let mut store_adapter = SignalProtocolStoreAdapter::new(
                device_store_arc.clone(),
                self.signal_cache.clone(),
            );

            let mut stores = wacore::send::SignalStores {
                session_store: &mut store_adapter.session_store,
                identity_store: &mut store_adapter.identity_store,
                prekey_store: &mut store_adapter.pre_key_store,
                signed_prekey_store: &store_adapter.signed_pre_key_store,
                sender_key_store: &mut store_adapter.sender_key_store,
            };

            // Consume forget marks - these participants need fresh SKDMs (matches WhatsApp Web)
            // markForgetSenderKey is called during retry handling, this consumes those marks
            let marked_for_fresh_skdm =
                self.consume_forget_marks(&to_str).await.unwrap_or_default();

            // Determine which devices need SKDM distribution
            let skdm_target_devices: Option<Vec<Jid>> = if force_skdm {
                None
            } else {
                let known_recipients = self
                    .persistence_manager
                    .get_skdm_recipients(&to_str)
                    .await
                    .unwrap_or_default();

                if known_recipients.is_empty() {
                    None
                } else {
                    let jids_to_resolve: Vec<Jid> = group_info
                        .participants
                        .iter()
                        .map(|jid| jid.to_non_ad())
                        .collect();

                    match SendContextResolver::resolve_devices(self, &jids_to_resolve).await {
                        Ok(all_devices) => {
                            use std::collections::HashSet;

                            let known_set: HashSet<DeviceKey<'_>> =
                                known_recipients.iter().map(|j| j.device_key()).collect();

                            let new_devices: Vec<Jid> = all_devices
                                .into_iter()
                                .filter(|device| !known_set.contains(&device.device_key()))
                                .collect();

                            if new_devices.is_empty() {
                                Some(vec![])
                            } else {
                                log::debug!(
                                    "Found {} new devices needing SKDM for group {}",
                                    new_devices.len(),
                                    to
                                );
                                Some(new_devices)
                            }
                        }
                        Err(e) => {
                            log::warn!("Failed to resolve devices for SKDM check: {:?}", e);
                            None
                        }
                    }
                }
            };

            // Merge devices marked for fresh SKDM (from retry/error handling)
            let skdm_target_devices: Option<Vec<Jid>> = if !marked_for_fresh_skdm.is_empty() {
                match skdm_target_devices {
                    None => None,
                    Some(mut devices) => {
                        for marked_jid_str in &marked_for_fresh_skdm {
                            if let Ok(marked_jid) = marked_jid_str.parse::<Jid>()
                                && !devices.iter().any(|d| d.device_eq(&marked_jid))
                            {
                                log::debug!(
                                    "Adding {} to SKDM targets (marked for fresh key)",
                                    marked_jid_str
                                );
                                devices.push(marked_jid);
                            }
                        }
                        Some(devices)
                    }
                }
            } else {
                skdm_target_devices
            };

            let is_full_distribution = force_skdm || skdm_target_devices.is_none();
            let devices_receiving_skdm: Vec<Jid> = skdm_target_devices.clone().unwrap_or_default();

            match wacore::send::prepare_group_stanza(
                &mut stores,
                self,
                &mut group_info,
                &own_jid,
                &own_lid,
                account_info.as_ref(),
                to.clone(),
                message,
                request_id.clone(),
                force_skdm,
                skdm_target_devices,
                edit.clone(),
                &extra_stanza_nodes,
            )
            .await
            {
                Ok(stanza) => {
                    skdm_update = Some(SkdmUpdate {
                        to_str: to_str.clone(),
                        devices: devices_receiving_skdm,
                        is_full_distribution,
                        participants: group_info.participants.clone(),
                    });
                    stanza
                }
                Err(e) => {
                    if let Some(SignalProtocolError::NoSenderKeyState(_)) =
                        e.downcast_ref::<SignalProtocolError>()
                    {
                        log::warn!("No sender key for group {}, forcing distribution.", to);

                        // Clear SKDM recipients since we're rotating the key
                        if let Err(e) = self
                            .persistence_manager
                            .clear_skdm_recipients(&to_str)
                            .await
                        {
                            log::warn!("Failed to clear SKDM recipients: {:?}", e);
                        }

                        let mut store_adapter_retry = SignalProtocolStoreAdapter::new(
                            device_store_arc.clone(),
                            self.signal_cache.clone(),
                        );
                        let mut stores_retry = wacore::send::SignalStores {
                            session_store: &mut store_adapter_retry.session_store,
                            identity_store: &mut store_adapter_retry.identity_store,
                            prekey_store: &mut store_adapter_retry.pre_key_store,
                            signed_prekey_store: &store_adapter_retry.signed_pre_key_store,
                            sender_key_store: &mut store_adapter_retry.sender_key_store,
                        };

                        let retry_stanza = wacore::send::prepare_group_stanza(
                            &mut stores_retry,
                            self,
                            &mut group_info,
                            &own_jid,
                            &own_lid,
                            account_info.as_ref(),
                            to,
                            message,
                            request_id,
                            true, // Force distribution on retry
                            None, // Distribute to all devices
                            edit.clone(),
                            &extra_stanza_nodes,
                        )
                        .await?;

                        // Retry is always full distribution (rotated sender key)
                        skdm_update = Some(SkdmUpdate {
                            to_str,
                            devices: vec![],
                            is_full_distribution: true,
                            participants: group_info.participants.clone(),
                        });
                        retry_stanza
                    } else {
                        return Err(e);
                    }
                }
            }
        } else {
            // Direct message: Acquire lock only during encryption

            // Ensure E2E sessions exist before encryption (matches WhatsApp Web)
            // This deduplicates concurrent prekey fetches for the same recipient
            let recipient_devices = self.get_user_devices(std::slice::from_ref(&to)).await?;
            self.ensure_e2e_sessions(recipient_devices).await?;

            // Resolve encryption JID and prepare lock acquisition
            let encryption_jid = self.resolve_encryption_jid(&to).await;
            let signal_addr_str = encryption_jid.to_protocol_address_string();

            // Store serialized message bytes for retry (lightweight)
            self.add_recent_message(to.clone(), request_id.clone(), message)
                .await;

            let device_snapshot = self.persistence_manager.get_device_snapshot().await;
            let own_jid = device_snapshot
                .pn
                .clone()
                .ok_or_else(|| anyhow::Error::from(crate::client::ClientError::NotLoggedIn))?;
            let account_info = device_snapshot.account.clone();

            // Include tctoken in 1:1 messages (matches WhatsApp Web behavior).
            // Skip for newsletters, groups, and own JID.
            let mut extra_stanza_nodes = extra_stanza_nodes;
            if !to.is_group() && !to.is_newsletter() {
                self.maybe_include_tc_token(&to, &mut extra_stanza_nodes)
                    .await;
            }

            // Acquire lock only for encryption
            let session_mutex = self
                .session_locks
                .get_with_by_ref(&signal_addr_str, async {
                    std::sync::Arc::new(async_lock::Mutex::new(()))
                })
                .await;
            let _session_guard = session_mutex.lock().await;

            let device_store_arc = self.persistence_manager.get_device_arc().await;
            let mut store_adapter =
                SignalProtocolStoreAdapter::new(device_store_arc, self.signal_cache.clone());

            let mut stores = wacore::send::SignalStores {
                session_store: &mut store_adapter.session_store,
                identity_store: &mut store_adapter.identity_store,
                prekey_store: &mut store_adapter.pre_key_store,
                signed_prekey_store: &store_adapter.signed_pre_key_store,
                sender_key_store: &mut store_adapter.sender_key_store,
            };

            wacore::send::prepare_dm_stanza(
                &mut stores,
                self,
                &own_jid,
                account_info.as_ref(),
                to,
                message,
                request_id,
                edit,
                &extra_stanza_nodes,
            )
            .await?
        };

        self.send_node(stanza_to_send).await?;

        // Update SKDM recipient cache AFTER server ACK (matches WhatsApp Web behavior).
        // WA Web only calls markHasSenderKey() after the server confirms receipt.
        if let Some(update) = skdm_update {
            self.update_skdm_recipients(
                &update.to_str,
                &update.devices,
                update.is_full_distribution,
                &update.participants,
            )
            .await;
        }

        // Flush cached Signal state to DB after encryption
        if let Err(e) = self.flush_signal_cache().await {
            log::error!("Failed to flush signal cache after send_message_impl: {e:?}");
        }

        Ok(())
    }

    /// Look up and include a tctoken in outgoing 1:1 message stanza nodes.
    ///
    /// If a valid (non-expired) token exists, adds a `<tctoken>` child node.
    /// If the token is missing or expired, attempts to issue new tokens via IQ.
    async fn maybe_include_tc_token(&self, to: &Jid, extra_nodes: &mut Vec<Node>) {
        use wacore::iq::tctoken::{
            IssuePrivacyTokensSpec, build_tc_token_node, is_tc_token_expired,
            should_send_new_tc_token,
        };
        use wacore::store::traits::TcTokenEntry;

        // Skip for own JID — no need to send privacy token to ourselves
        let snapshot = self.persistence_manager.get_device_snapshot().await;
        let is_self = snapshot
            .pn
            .as_ref()
            .is_some_and(|pn| pn.is_same_user_as(to))
            || snapshot
                .lid
                .as_ref()
                .is_some_and(|lid| lid.is_same_user_as(to));
        if is_self {
            return;
        }

        // Resolve the destination to a LID for token lookup
        let token_jid = if to.is_lid() {
            to.user.clone()
        } else {
            match self.lid_pn_cache.get_current_lid(&to.user).await {
                Some(lid) => lid,
                None => to.user.clone(),
            }
        };

        let backend = self.persistence_manager.backend();

        // Look up existing token
        let existing = match backend.get_tc_token(&token_jid).await {
            Ok(entry) => entry,
            Err(e) => {
                log::warn!(target: "Client/TcToken", "Failed to get tc_token for {}: {e}", token_jid);
                return;
            }
        };

        match existing {
            Some(entry) if !is_tc_token_expired(entry.token_timestamp) => {
                // Valid token — include it in the stanza
                extra_nodes.push(build_tc_token_node(&entry.token));

                // Check if we should re-issue (bucket boundary crossed).
                // Update sender_timestamp to mark we've sent our token in this bucket.
                if should_send_new_tc_token(entry.sender_timestamp) {
                    let now = wacore::time::now_secs();
                    let updated_entry = TcTokenEntry {
                        sender_timestamp: Some(now),
                        ..entry
                    };
                    if let Err(e) = backend.put_tc_token(&token_jid, &updated_entry).await {
                        log::warn!(target: "Client/TcToken", "Failed to update sender_timestamp: {e}");
                    }
                }
            }
            _ => {
                // Token missing or expired — try to issue
                let to_lid = self.resolve_to_lid_jid(to).await;
                match self
                    .execute(IssuePrivacyTokensSpec::new(std::slice::from_ref(&to_lid)))
                    .await
                {
                    Ok(response) => {
                        let now = wacore::time::now_secs();
                        for received in &response.tokens {
                            let entry = TcTokenEntry {
                                token: received.token.clone(),
                                token_timestamp: received.timestamp,
                                sender_timestamp: Some(now),
                            };

                            // Store the received token
                            let store_jid = received.jid.user.clone();
                            if let Err(e) = backend.put_tc_token(&store_jid, &entry).await {
                                log::warn!(target: "Client/TcToken", "Failed to store issued tc_token: {e}");
                            }

                            // Include in message stanza
                            if !received.token.is_empty() {
                                extra_nodes.push(build_tc_token_node(&received.token));
                            }
                        }
                    }
                    Err(e) => {
                        log::debug!(target: "Client/TcToken", "Failed to issue tc_token for {}: {e}", to_lid);
                        // Don't fail the message send — tctoken is optional
                    }
                }
            }
        }
    }

    /// Look up a valid (non-expired) tctoken for a JID. Returns the raw token bytes if found.
    ///
    /// Used by profile picture, presence subscribe, and other features that need tctoken gating.
    pub(crate) async fn lookup_tc_token_for_jid(&self, jid: &Jid) -> Option<Vec<u8>> {
        use wacore::iq::tctoken::is_tc_token_expired;

        let token_jid = if jid.is_lid() {
            jid.user.clone()
        } else {
            match self.lid_pn_cache.get_current_lid(&jid.user).await {
                Some(lid) => lid,
                None => jid.user.clone(),
            }
        };

        let backend = self.persistence_manager.backend();
        match backend.get_tc_token(&token_jid).await {
            Ok(Some(entry)) if !is_tc_token_expired(entry.token_timestamp) => Some(entry.token),
            Ok(_) => None,
            Err(e) => {
                log::warn!(target: "Client/TcToken", "Failed to get tc_token for {}: {e}", token_jid);
                None
            }
        }
    }

    /// Resolve a JID to its LID form for tc_token storage.
    async fn resolve_to_lid_jid(&self, jid: &Jid) -> Jid {
        if jid.is_lid() {
            return jid.clone();
        }

        if let Some(lid_user) = self.lid_pn_cache.get_current_lid(&jid.user).await {
            Jid::new(&lid_user, "lid")
        } else {
            jid.clone()
        }
    }
}

#[cfg(test)]
mod tests {
    use super::*;
    use std::str::FromStr;

    #[test]
    fn test_revoke_type_default_is_sender() {
        // RevokeType::Sender is the default (for deleting own messages)
        let revoke_type = RevokeType::default();
        assert_eq!(revoke_type, RevokeType::Sender);
    }

    #[test]
    fn test_force_skdm_only_for_admin_revoke() {
        // Admin revokes require force_skdm=true to get proper message structure
        // with phash, <participants>, and <device-identity> that WhatsApp Web uses.
        // Without this, the server returns error 479.
        let sender_jid = Jid::from_str("123456@s.whatsapp.net").unwrap();

        let sender_revoke = RevokeType::Sender;
        let admin_revoke = RevokeType::Admin {
            original_sender: sender_jid,
        };

        // This matches the logic in revoke_message()
        let force_skdm_sender = matches!(sender_revoke, RevokeType::Admin { .. });
        let force_skdm_admin = matches!(admin_revoke, RevokeType::Admin { .. });

        assert!(!force_skdm_sender, "Sender revoke should NOT force SKDM");
        assert!(force_skdm_admin, "Admin revoke MUST force SKDM");
    }

    #[test]
    fn test_sender_revoke_message_key_structure() {
        // Sender revoke (edit="7"): from_me=true, participant=None
        // The sender is identified by from_me=true, no participant field needed
        let to = Jid::from_str("120363040237990503@g.us").unwrap();
        let message_id = "3EB0ABC123".to_string();

        let (from_me, participant, edit_attr) = match RevokeType::Sender {
            RevokeType::Sender => (
                true,
                None,
                crate::types::message::EditAttribute::SenderRevoke,
            ),
            RevokeType::Admin { original_sender } => (
                false,
                Some(original_sender.to_non_ad().to_string()),
                crate::types::message::EditAttribute::AdminRevoke,
            ),
        };

        assert!(from_me, "Sender revoke must have from_me=true");
        assert!(
            participant.is_none(),
            "Sender revoke must NOT set participant"
        );
        assert_eq!(edit_attr.to_string_val(), "7");

        let revoke_message = wa::Message {
            protocol_message: Some(Box::new(wa::message::ProtocolMessage {
                key: Some(wa::MessageKey {
                    remote_jid: Some(to.to_string()),
                    from_me: Some(from_me),
                    id: Some(message_id.clone()),
                    participant,
                }),
                r#type: Some(wa::message::protocol_message::Type::Revoke as i32),
                ..Default::default()
            })),
            ..Default::default()
        };

        let proto_msg = revoke_message.protocol_message.unwrap();
        let key = proto_msg.key.unwrap();
        assert_eq!(key.from_me, Some(true));
        assert_eq!(key.participant, None);
        assert_eq!(key.id, Some(message_id));
    }

    #[test]
    fn test_admin_revoke_message_key_structure() {
        // Admin revoke (edit="8"): from_me=false, participant=original_sender
        // The participant field identifies whose message is being deleted
        let to = Jid::from_str("120363040237990503@g.us").unwrap();
        let message_id = "3EB0ABC123".to_string();
        let original_sender = Jid::from_str("236395184570386:22@lid").unwrap();

        let revoke_type = RevokeType::Admin {
            original_sender: original_sender.clone(),
        };
        let (from_me, participant, edit_attr) = match revoke_type {
            RevokeType::Sender => (
                true,
                None,
                crate::types::message::EditAttribute::SenderRevoke,
            ),
            RevokeType::Admin { original_sender } => (
                false,
                Some(original_sender.to_non_ad().to_string()),
                crate::types::message::EditAttribute::AdminRevoke,
            ),
        };

        assert!(!from_me, "Admin revoke must have from_me=false");
        assert!(
            participant.is_some(),
            "Admin revoke MUST set participant to original sender"
        );
        assert_eq!(edit_attr.to_string_val(), "8");

        let revoke_message = wa::Message {
            protocol_message: Some(Box::new(wa::message::ProtocolMessage {
                key: Some(wa::MessageKey {
                    remote_jid: Some(to.to_string()),
                    from_me: Some(from_me),
                    id: Some(message_id.clone()),
                    participant: participant.clone(),
                }),
                r#type: Some(wa::message::protocol_message::Type::Revoke as i32),
                ..Default::default()
            })),
            ..Default::default()
        };

        let proto_msg = revoke_message.protocol_message.unwrap();
        let key = proto_msg.key.unwrap();
        assert_eq!(key.from_me, Some(false));
        // Participant should be the original sender with device number stripped
        assert_eq!(key.participant, Some("236395184570386@lid".to_string()));
        assert_eq!(key.id, Some(message_id));
    }

    #[test]
    fn test_admin_revoke_preserves_lid_format() {
        // LID JIDs must NOT be converted to PN (phone number) format.
        // This was a bug that caused error 479 - the participant field must
        // preserve the original JID format exactly (with device stripped).
        let lid_sender = Jid::from_str("236395184570386:22@lid").unwrap();
        let participant_str = lid_sender.to_non_ad().to_string();

        // Must preserve @lid suffix, device number stripped
        assert_eq!(participant_str, "236395184570386@lid");
        assert!(
            participant_str.ends_with("@lid"),
            "LID participant must preserve @lid suffix"
        );
    }

    // SKDM Recipient Filtering Tests - validates DeviceKey-based filtering

    #[test]
    fn test_skdm_recipient_filtering_basic() {
        use std::collections::HashSet;

        let known_recipients: Vec<Jid> = [
            "1234567890:0@s.whatsapp.net",
            "1234567890:5@s.whatsapp.net",
            "9876543210:0@s.whatsapp.net",
        ]
        .into_iter()
        .map(|s| Jid::from_str(s).unwrap())
        .collect();

        let all_devices: Vec<Jid> = [
            "1234567890:0@s.whatsapp.net",
            "1234567890:5@s.whatsapp.net",
            "9876543210:0@s.whatsapp.net",
            "5555555555:0@s.whatsapp.net", // new
        ]
        .into_iter()
        .map(|s| Jid::from_str(s).unwrap())
        .collect();

        let known_set: HashSet<DeviceKey<'_>> =
            known_recipients.iter().map(|j| j.device_key()).collect();

        let new_devices: Vec<Jid> = all_devices
            .into_iter()
            .filter(|device| !known_set.contains(&device.device_key()))
            .collect();

        assert_eq!(new_devices.len(), 1);
        assert_eq!(new_devices[0].user, "5555555555");
    }

    #[test]
    fn test_skdm_recipient_filtering_lid_jids() {
        use std::collections::HashSet;

        let known_recipients: Vec<Jid> = [
            "236395184570386:91@lid",
            "129171292463295:0@lid",
            "45857667830004:14@lid",
        ]
        .into_iter()
        .map(|s| Jid::from_str(s).unwrap())
        .collect();

        let all_devices: Vec<Jid> = [
            "236395184570386:91@lid",
            "129171292463295:0@lid",
            "45857667830004:14@lid",
            "45857667830004:15@lid", // new
        ]
        .into_iter()
        .map(|s| Jid::from_str(s).unwrap())
        .collect();

        let known_set: HashSet<DeviceKey<'_>> =
            known_recipients.iter().map(|j| j.device_key()).collect();

        let new_devices: Vec<Jid> = all_devices
            .into_iter()
            .filter(|device| !known_set.contains(&device.device_key()))
            .collect();

        assert_eq!(new_devices.len(), 1);
        assert_eq!(new_devices[0].user, "45857667830004");
        assert_eq!(new_devices[0].device, 15);
    }

    #[test]
    fn test_skdm_recipient_filtering_all_known() {
        use std::collections::HashSet;

        let known_recipients: Vec<Jid> =
            ["1234567890:0@s.whatsapp.net", "1234567890:5@s.whatsapp.net"]
                .into_iter()
                .map(|s| Jid::from_str(s).unwrap())
                .collect();

        let all_devices: Vec<Jid> = ["1234567890:0@s.whatsapp.net", "1234567890:5@s.whatsapp.net"]
            .into_iter()
            .map(|s| Jid::from_str(s).unwrap())
            .collect();

        let known_set: HashSet<DeviceKey<'_>> =
            known_recipients.iter().map(|j| j.device_key()).collect();

        let new_devices: Vec<Jid> = all_devices
            .into_iter()
            .filter(|device| !known_set.contains(&device.device_key()))
            .collect();

        assert!(new_devices.is_empty());
    }

    #[test]
    fn test_skdm_recipient_filtering_all_new() {
        use std::collections::HashSet;

        let known_recipients: Vec<Jid> = vec![];

        let all_devices: Vec<Jid> = ["1234567890:0@s.whatsapp.net", "9876543210:0@s.whatsapp.net"]
            .into_iter()
            .map(|s| Jid::from_str(s).unwrap())
            .collect();

        let known_set: HashSet<DeviceKey<'_>> =
            known_recipients.iter().map(|j| j.device_key()).collect();

        let new_devices: Vec<Jid> = all_devices
            .clone()
            .into_iter()
            .filter(|device| !known_set.contains(&device.device_key()))
            .collect();

        assert_eq!(new_devices.len(), all_devices.len());
    }

    #[test]
    fn test_device_key_comparison() {
        // Jid parse/display normalizes :0 (omitted in Display, missing ':N' parses as device 0).
        // This test ensures DeviceKey comparisons work correctly under that normalization.
        let test_cases = [
            (
                "1234567890:0@s.whatsapp.net",
                "1234567890@s.whatsapp.net",
                true,
            ),
            (
                "1234567890:5@s.whatsapp.net",
                "1234567890:5@s.whatsapp.net",
                true,
            ),
            (
                "1234567890:5@s.whatsapp.net",
                "1234567890:6@s.whatsapp.net",
                false,
            ),
            ("236395184570386:91@lid", "236395184570386:91@lid", true),
            ("236395184570386:0@lid", "236395184570386@lid", true),
            ("user1@s.whatsapp.net", "user2@s.whatsapp.net", false),
        ];

        for (jid1_str, jid2_str, should_match) in test_cases {
            let jid1: Jid = jid1_str.parse().expect("should parse jid1");
            let jid2: Jid = jid2_str.parse().expect("should parse jid2");

            let key1 = jid1.device_key();
            let key2 = jid2.device_key();

            assert_eq!(
                key1 == key2,
                should_match,
                "DeviceKey comparison failed for '{}' vs '{}': expected match={}, got match={}",
                jid1_str,
                jid2_str,
                should_match,
                key1 == key2
            );

            assert_eq!(
                jid1.device_eq(&jid2),
                should_match,
                "device_eq failed for '{}' vs '{}'",
                jid1_str,
                jid2_str
            );
        }
    }

    #[test]
    fn test_skdm_filtering_large_group() {
        use std::collections::HashSet;

        let mut known_recipients: Vec<Jid> = Vec::with_capacity(1000);
        let mut all_devices: Vec<Jid> = Vec::with_capacity(1010);

        for i in 0..1000i64 {
            let jid_str = format!("{}:1@lid", 100000000000000i64 + i);
            let jid = Jid::from_str(&jid_str).unwrap();
            known_recipients.push(jid.clone());
            all_devices.push(jid);
        }

        for i in 1000i64..1010i64 {
            let jid_str = format!("{}:1@lid", 100000000000000i64 + i);
            all_devices.push(Jid::from_str(&jid_str).unwrap());
        }

        let known_set: HashSet<DeviceKey<'_>> =
            known_recipients.iter().map(|j| j.device_key()).collect();

        let new_devices: Vec<Jid> = all_devices
            .into_iter()
            .filter(|device| !known_set.contains(&device.device_key()))
            .collect();

        assert_eq!(new_devices.len(), 10);
    }
}