send.rs

use crate::client::Client;
use crate::types::message::EditAttribute;
use anyhow::anyhow;
use log::debug;
use wacore::client::context::SendContextResolver;
use wacore::libsignal::protocol::SignalProtocolError;
use wacore::types::jid::JidExt;
use wacore::types::message::AddressingMode;
#[cfg(test)]
use wacore_binary::DeviceKey;
use wacore_binary::Node;
use wacore_binary::builder::NodeBuilder;
use wacore_binary::{Jid, JidExt as _, Server};
use waproto::whatsapp as wa;

/// Options for [`Client::send_message_with_options`].
#[derive(Debug, Clone, Default)]
pub struct SendOptions {
    /// Override the auto-generated message ID.
    /// Useful for resending a failed message with the same ID or idempotency.
    pub message_id: Option<String>,
    /// Extra XML child nodes on the message stanza.
    pub extra_stanza_nodes: Vec<Node>,
    /// Ephemeral duration in seconds. Sets `contextInfo.expiration` on the
    /// message (WA Web `EProtoGenerator.js:183` parity).
    /// Common values: 86400 (24h), 604800 (7d), 7776000 (90d).
    pub ephemeral_expiration: Option<u32>,
}

/// Result of a successfully sent message.
#[derive(Debug, Clone, PartialEq, Eq)]
pub struct SendResult {
    pub message_id: String,
    pub to: Jid,
}

impl SendResult {
    /// `participant` is `None` -- only valid for the sender's own messages.
    pub fn message_key(&self) -> wa::MessageKey {
        wa::MessageKey {
            remote_jid: Some(self.to.to_string()),
            from_me: Some(true),
            id: Some(self.message_id.clone()),
            participant: None,
        }
    }
}

/// Duration for pinned messages. Default is 7 days (matches WA Web).
#[derive(Debug, Clone, Copy, PartialEq, Eq, Default)]
#[non_exhaustive]
pub enum PinDuration {
    Hours24,
    #[default]
    Days7,
    Days30,
}

impl PinDuration {
    fn as_secs(self) -> u32 {
        match self {
            Self::Hours24 => 86_400,
            Self::Days7 => 604_800,
            Self::Days30 => 2_592_000,
        }
    }
}

/// Specifies who is revoking (deleting) the message.
#[derive(Debug, Clone, PartialEq, Eq, Default)]
#[non_exhaustive]
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 },
}

/// Derive stanza-level edit attribute and meta node from message content.
fn infer_stanza_metadata(msg: &wa::Message) -> (Option<EditAttribute>, Option<Node>) {
    if msg.pin_in_chat_message.is_some() {
        return (Some(EditAttribute::PinInChat), None);
    }

    // Poll messages
    if msg.poll_creation_message.is_some()
        || msg.poll_creation_message_v2.is_some()
        || msg.poll_creation_message_v3.is_some()
    {
        return (None, Some(meta_node("polltype", "creation")));
    }
    if let Some(ref poll_update) = msg.poll_update_message
        && poll_update.vote.is_some()
    {
        return (None, Some(meta_node("polltype", "vote")));
    }
    // TODO: polltype="result_snapshot" for poll_result_snapshot_message (gated behind AB flag)

    // Event messages
    if msg.event_message.is_some() {
        return (None, Some(meta_node("event_type", "creation")));
    }
    if msg.enc_event_response_message.is_some() {
        return (None, Some(meta_node("event_type", "response")));
    }
    if let Some(ref sec) = msg.secret_encrypted_message
        && sec.secret_enc_type
            == Some(wa::message::secret_encrypted_message::SecretEncType::EventEdit as i32)
    {
        return (None, Some(meta_node("event_type", "edit")));
    }

    (None, None)
}

fn meta_node(key: &'static str, value: &'static str) -> Node {
    NodeBuilder::new("meta").attr(key, value).build()
}

/// Derive the `<biz>` stanza child for native-flow interactive messages.
/// All native flow types use the same nested structure (confirmed via protocol capture).
fn infer_biz_node(msg: &wa::Message) -> Option<Node> {
    let interactive = extract_interactive_message(msg)?;
    let wa::message::interactive_message::InteractiveMessage::NativeFlowMessage(nf) =
        interactive.interactive_message.as_ref()?
    else {
        return None;
    };

    let first_button_name = nf.buttons.first()?.name.as_deref()?;
    let flow_name = button_name_to_flow_name(first_button_name);

    Some(
        NodeBuilder::new("biz")
            .children([NodeBuilder::new("interactive")
                .attr("type", "native_flow")
                .attr("v", "1")
                .children([NodeBuilder::new("native_flow")
                    .attr("name", flow_name)
                    .build()])
                .build()])
            .build(),
    )
}

fn extract_interactive_message(msg: &wa::Message) -> Option<&wa::message::InteractiveMessage> {
    // Only checks documentWithCaptionMessage wrapper (for media headers) and direct field.
    // Does not use unwrap_message() since we need the InteractiveMessage specifically.
    if let Some(ref doc) = msg.document_with_caption_message
        && let Some(ref inner) = doc.message
        && let Some(ref im) = inner.interactive_message
    {
        return Some(im);
    }
    msg.interactive_message.as_deref()
}

fn button_name_to_flow_name(button_name: &str) -> &str {
    match button_name {
        "review_and_pay" => "order_details",
        "payment_info" => "payment_info",
        "review_order" | "order_status" => "order_status",
        "payment_status" => "payment_status",
        "payment_method" => "payment_method",
        "payment_reminder" => "payment_reminder",
        "open_webview" => "message_with_link",
        "message_with_link_status" => "message_with_link_status",
        "cta_url" => "cta_url",
        "cta_call" => "cta_call",
        "cta_copy" => "cta_copy",
        "cta_catalog" => "cta_catalog",
        "catalog_message" => "catalog_message",
        "quick_reply" => "quick_reply",
        "galaxy_message" => "galaxy_message",
        "booking_confirmation" => "booking_confirmation",
        "call_permission_request" => "call_permission_request",
        other => other,
    }
}

fn build_revoke_message(
    remote_jid: &Jid,
    from_me: bool,
    message_id: String,
    participant: Option<String>,
) -> wa::Message {
    wa::Message {
        protocol_message: Some(Box::new(wa::message::ProtocolMessage {
            key: Some(wa::MessageKey {
                remote_jid: Some(remote_jid.to_string()),
                from_me: Some(from_me),
                id: Some(message_id),
                participant,
            }),
            r#type: Some(wa::message::protocol_message::Type::Revoke as i32),
            ..Default::default()
        })),
        ..Default::default()
    }
}

impl Client {
    /// Send a message to a user, group, or newsletter.
    ///
    /// Newsletter messages are sent as plaintext (no E2E encryption).
    /// For status/story updates use [`Client::status()`] instead.
    pub async fn send_message(
        &self,
        to: Jid,
        message: wa::Message,
    ) -> Result<SendResult, 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,
        mut message: wa::Message,
        options: SendOptions,
    ) -> Result<SendResult, anyhow::Error> {
        if let Some(exp) = options.ephemeral_expiration
            && exp > 0
        {
            use wacore::proto_helpers::MessageExt;
            if !message.set_ephemeral_expiration(exp) {
                // Bare `conversation` messages have no contextInfo field.
                log::warn!("Could not set contextInfo.expiration on this message type");
            }
        }

        let request_id = match options.message_id {
            Some(id) => id,
            None => self.generate_message_id().await,
        };
        // Both paths below consume `to` and `request_id`, so save copies for the result.
        let result = SendResult {
            message_id: request_id.clone(),
            to: to.clone(),
        };

        // Newsletters are not E2E encrypted — send as plaintext via SMAX stanza.
        // Matches WA Web's OutMessagePublishNewsletterRequest + ContentType mixins.
        if to.is_newsletter() {
            use prost::Message as _;
            let stanza_type = wacore::send::stanza_type_from_message(&message);
            let (_, meta_node) = infer_stanza_metadata(&message);
            let mut plaintext_builder = NodeBuilder::new("plaintext");
            if let Some(mt) = wacore::send::media_type_from_message(&message) {
                plaintext_builder = plaintext_builder.attr("mediatype", mt);
            }
            let mut children = vec![plaintext_builder.bytes(message.encode_to_vec()).build()];
            children.extend(meta_node);
            children.extend(options.extra_stanza_nodes);
            let stanza = NodeBuilder::new("message")
                .attr("to", to)
                .attr("type", stanza_type)
                .attr("id", &request_id)
                .children(children)
                .build();
            self.send_node(stanza).await?;
            return Ok(result);
        }

        let (edit, inferred_meta) = infer_stanza_metadata(&message);
        let inferred_biz = infer_biz_node(&message);

        let extra_nodes = if inferred_meta.is_none() && inferred_biz.is_none() {
            options.extra_stanza_nodes
        } else {
            let mut nodes = Vec::with_capacity(2 + options.extra_stanza_nodes.len());
            nodes.extend(inferred_meta);
            nodes.extend(inferred_biz);
            nodes.extend(options.extra_stanza_nodes);
            nodes
        };
        self.send_message_impl(
            to,
            &message,
            Some(request_id),
            false,
            false,
            edit,
            extra_nodes,
        )
        .await?;
        Ok(result)
    }

    /// Send a status/story update using sender-key encryption.
    ///
    /// Status uses LID addressing (matches `WAWebEncryptAndSendStatusMsg`):
    /// LID recipients pass through, PN recipients are resolved to LID via
    /// `Client::get_lid_pn_entry` (cache-aside), and unresolvable recipients
    /// are skipped silently. The resulting `GroupInfo` carries
    /// `AddressingMode::Lid`; `prepare_group_stanza` signs with `own_lid`
    /// and emits `addressing_mode="lid"` on the stanza. Errors only if no
    /// recipient could be resolved.
    pub(crate) async fn send_status_message(
        &self,
        message: wa::Message,
        recipients: &[Jid],
        options: crate::features::status::StatusSendOptions,
    ) -> Result<SendResult, 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 mut device_snapshot = self.persistence_manager.get_device_snapshot().await;
        let account_info = device_snapshot.account.take();
        let own_jid = device_snapshot
            .pn
            .take()
            .ok_or(crate::client::ClientError::NotLoggedIn)?;
        // Status is LID-addressed (matches WA Web post-LID-migration). Without
        // a real device LID we can't sign or fan out correctly; refuse rather
        // than silently emit `addressing_mode="lid"` with a PN sender.
        let own_lid = device_snapshot.lid.take().ok_or_else(|| {
            anyhow!(
                "Cannot send status: device has no LID yet. Finish pairing / LID \
                 migration before posting status."
            )
        })?;

        // Fail fast for any JID that isn't a user (PN or LID). Mirrors WA
        // Web's `asUserWidOrThrow` inside `toUserLid`: non-user inputs are a
        // programming bug, not something to silently drop during resolution.
        for jid in recipients {
            if !(jid.is_pn() || jid.is_lid()) {
                return Err(anyhow!(
                    "Invalid status recipient {}: must be a user JID (PN or LID), \
                     not a group/broadcast/newsletter/hosted/etc.",
                    jid
                ));
            }
        }

        use std::collections::HashMap;
        let mut resolved: Vec<Option<Jid>> = Vec::with_capacity(recipients.len());
        let mut lid_to_pn_map: HashMap<wacore_binary::CompactString, Jid> =
            HashMap::with_capacity(recipients.len() + 1);
        for jid in recipients {
            if let Some(lid_jid) = self.resolve_recipient_to_lid(jid).await {
                if jid.is_pn() {
                    lid_to_pn_map.insert(lid_jid.user.clone(), jid.to_non_ad());
                }
                resolved.push(Some(lid_jid));
            } else {
                resolved.push(None);
            }
        }
        lid_to_pn_map.insert(own_lid.user.clone(), own_jid.to_non_ad());

        let participants = wacore::send::assemble_status_participants(resolved, &own_lid)?;
        let mut group_info =
            GroupInfo::with_lid_to_pn_map(participants, AddressingMode::Lid, lid_to_pn_map);

        self.add_recent_message(&to, &request_id, &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;
            // Sender key name tracks the addressing mode of the group stanza.
            // Since status now uses LID addressing (see send_status_message
            // header), the key is stored under own_lid, matching the address
            // prepare_group_stanza derives internally.
            let sender_address = own_lid.to_protocol_address();
            let sender_key_name = SenderKeyName::from_parts(&to_str, sender_address.as_str());

            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 = self.signal_adapter_from(device_store_arc.clone());
        let mut stores = store_adapter.as_signal_stores();

        // Determine which devices need SKDM using the unified per-device map
        let skdm_target_devices: Option<Vec<Jid>> = if force_skdm {
            None
        } else {
            self.resolve_skdm_targets(&to_str, &group_info, &own_lid)
                .await
        };

        // `<meta status_setting>` describes the POSTER's privacy on their own
        // status. Reactions go through WA Web's addon path and never visit
        // `WAWebEncryptAndSendStatusMsg`; attaching the meta on a reaction
        // gets the stanza NACK'd with 479 (SmaxInvalid). Revokes also skip it.
        let extra_stanza_nodes = if wacore::send::status_carries_privacy_meta(&message) {
            vec![
                NodeBuilder::new("meta")
                    .attr("status_setting", options.privacy.as_str())
                    .build(),
            ]
        } else {
            vec![]
        };

        let prepared = match wacore::send::prepare_group_stanza(
            &*self.runtime,
            &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(prepared) => prepared,
            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_sender_key_devices(&to_str)
                        .await
                    {
                        log::warn!(
                            "Failed to clear status SKDM recipients for {}: {:?}",
                            to_str,
                            e
                        );
                    }
                    self.sender_key_device_cache.invalidate(&to_str).await;

                    let mut store_adapter_retry =
                        self.signal_adapter_from(device_store_arc.clone());
                    let mut stores_retry = store_adapter_retry.as_signal_stores();

                    wacore::send::prepare_group_stanza(
                        &*self.runtime,
                        &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?
                } else {
                    return Err(e);
                }
            }
        };

        let stanza = self
            .ensure_status_participants(prepared.node, &group_info)
            .await?;

        let ack = if let Some(phash) = stanza
            .attrs()
            .optional_string("phash")
            .map(|s| s.into_owned())
        {
            let rx = self.register_ack_waiter(&request_id).await;
            Some((rx, phash))
        } else {
            None
        };

        if let Err(e) = self.send_node(stanza).await {
            if ack.is_some() {
                self.response_waiters.lock().await.remove(&request_id);
            }
            return Err(e.into());
        }

        if let Some((rx, phash)) = ack {
            self.spawn_phash_validation(rx, phash, to.clone(), true, request_id.clone());
        }

        self.update_sender_key_devices(&to_str, &prepared.skdm_devices)
            .await;

        for user in &prepared.stale_device_users {
            self.invalidate_device_cache(user).await;
        }

        self.flush_signal_cache_logged("send_status_message", None)
            .await;

        Ok(SendResult {
            message_id: request_id,
            to,
        })
    }

    /// Resolve which devices need SKDM. Returns `None` for full distribution
    /// (no cache data), or `Some(devices)` listing devices that need fresh SKDM.
    ///
    /// For LID mode, uses `group_info.phone_jid_for_lid_user` to query devices
    /// via PN when available (LID usync is unreliable for own JID), then
    /// converts the result back to LID. Same fallback as `prepare_group_stanza`.
    async fn resolve_skdm_targets(
        &self,
        group_jid: &str,
        group_info: &wacore::client::context::GroupInfo,
        own_sending_jid: &Jid,
    ) -> Option<Vec<Jid>> {
        use crate::sender_key_device_cache::SenderKeyDeviceMap;

        // Atomic get-or-init: if another task invalidated the cache during our
        // DB read, get_or_init's single-flight guarantee means the stale data
        // won't be inserted — the invalidation wins and the next caller re-inits.
        let pm = self.persistence_manager.clone();
        let cached_map = self
            .sender_key_device_cache
            .get_or_init(group_jid, async {
                let db_rows = pm
                    .get_sender_key_devices(group_jid)
                    .await
                    .unwrap_or_else(|e| {
                        log::warn!(
                            "Failed to read sender key devices for {}: {:?}",
                            group_jid,
                            e
                        );
                        vec![]
                    });
                std::sync::Arc::new(SenderKeyDeviceMap::from_db_rows(&db_rows))
            })
            .await;

        // No empty-cache early-exit: WA Web iterates an empty `senderKey` Map
        // as `false` per participant, so the filter below must run unconditionally.
        let is_lid_mode = group_info.addressing_mode == wacore::types::message::AddressingMode::Lid;
        let jids_to_resolve: Vec<Jid> = group_info
            .participants
            .iter()
            .map(|jid| {
                if is_lid_mode
                    && jid.is_lid()
                    && let Some(pn) = group_info.phone_jid_for_lid_user(&jid.user)
                {
                    return pn.to_non_ad();
                }
                jid.to_non_ad()
            })
            .collect();

        match SendContextResolver::resolve_devices(self, &jids_to_resolve).await {
            Ok(all_devices) => {
                let all_devices: Vec<Jid> = if is_lid_mode {
                    all_devices
                        .into_iter()
                        .map(|d| group_info.phone_device_jid_to_lid(&d))
                        .collect()
                } else {
                    all_devices
                };

                let needs_skdm: Vec<Jid> = all_devices
                    .into_iter()
                    .filter(|device| {
                        if device.is_hosted() {
                            return false;
                        }
                        if device.user == own_sending_jid.user
                            && device.device == own_sending_jid.device
                        {
                            return false;
                        }
                        // O(1) lookups into pre-indexed cache
                        !cached_map
                            .device_has_key(&device.user, device.device)
                            .unwrap_or(false)
                            || cached_map.is_user_forgotten(&device.user)
                    })
                    .collect();

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

    /// Update sender key device tracking after a successful group/status send.
    ///
    /// Called AFTER `send_node()` succeeds (WA Web: `markHasSenderKey` after server ACK).
    /// On full distribution, clears old state and marks the provided device list.
    /// On partial, marks only the specific SKDM recipients.
    ///
    /// The `all_resolved_devices` parameter carries the exact device list resolved
    /// for the stanza, avoiding a redundant `resolve_devices` call and preventing
    /// the clear-then-fail race where a transient resolver failure leaves the map empty.
    /// Mark devices as `has_key=true` after successful SKDM distribution.
    async fn update_sender_key_devices(&self, group_jid: &str, devices: &[Jid]) {
        if devices.is_empty() {
            return;
        }

        if let Err(e) = self
            .set_sender_key_status_for_devices(group_jid, devices, true, false)
            .await
        {
            log::warn!(
                "Failed to update sender key devices for {}: {:?}",
                group_jid,
                e
            );
        }
        self.sender_key_device_cache.invalidate(group_jid).await;
    }

    /// Spawn a background task to validate phash from server ack.
    /// On mismatch, invalidates sender key device cache and group info cache.
    fn spawn_phash_validation(
        &self,
        rx: futures::channel::oneshot::Receiver<std::sync::Arc<wacore_binary::OwnedNodeRef>>,
        our_phash: String,
        jid: Jid,
        invalidate_group_cache: bool,
        message_id: String,
    ) {
        let Some(client) = self.self_weak.get().and_then(|w| w.upgrade()) else {
            return;
        };
        self.runtime
            .spawn(Box::pin(async move {
                let ack = match wacore::runtime::timeout(
                    &*client.runtime,
                    std::time::Duration::from_secs(10),
                    rx,
                )
                .await
                {
                    Ok(Ok(node)) => node,
                    _ => {
                        // Remove leaked waiter to prevent keepalive suppression
                        client.response_waiters.lock().await.remove(&message_id);
                        return;
                    }
                };
                if let Some(server) = ack.get().get_attr("phash").map(|v| v.as_str())
                    && server != our_phash
                {
                    log::warn!(
                        "Phash mismatch for {jid}: ours={our_phash}, server={server}. Invalidating caches."
                    );
                    // DM phash covers both recipient + own devices
                    // (WA Web: syncDeviceListJob([recipient, me]))
                    if !jid.is_group() && !jid.is_status_broadcast() {
                        client.invalidate_device_cache(&jid.user).await;
                        if let Some(own_pn) =
                            &client.persistence_manager.get_device_snapshot().await.pn
                        {
                            client.invalidate_device_cache(&own_pn.user).await;
                        }
                    }
                    let jid_str = jid.to_string();
                    // Cache-only invalidation re-reads the same stale rows on
                    // the next send. Drop the persisted state too so the next
                    // send takes the full-distribution path. If the clear
                    // fails, fall back to deleting the bot's own sender key
                    // for the chat — the next send will see `!key_exists`
                    // and force_skdm without depending on the tracker.
                    if jid.is_group() || jid.is_status_broadcast() {
                        let cleared = client
                            .persistence_manager
                            .clear_sender_key_devices(&jid_str)
                            .await;
                        if let Err(e) = cleared {
                            log::warn!(
                                "phash mismatch: clear_sender_key_devices failed: {e} — \
                                 deleting own sender key as fallback to force redistribution"
                            );
                            use wacore::libsignal::store::sender_key_name::SenderKeyName;
                            use wacore::types::jid::JidExt;
                            let snapshot =
                                client.persistence_manager.get_device_snapshot().await;
                            for own in snapshot.lid.iter().chain(snapshot.pn.iter()) {
                                let sk =
                                    SenderKeyName::from_parts(&jid_str, own.to_protocol_address().as_str());
                                client.signal_cache.delete_sender_key(sk.cache_key()).await;
                            }
                            let _ = client
                                .flush_signal_cache_logged("phash-mismatch-fallback", None)
                                .await;
                        }
                    }
                    client.sender_key_device_cache.invalidate(&jid_str).await;
                    if invalidate_group_cache {
                        client.get_group_cache().await.invalidate(&jid).await;
                    }
                }
            }))
            .detach();
    }

    /// 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();
        self.require_pn().await?;

        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 = build_revoke_message(&to, from_me, message_id, participant);

        // 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
    }

    /// Pin a message in a chat for all participants.
    pub async fn pin_message(
        &self,
        chat: Jid,
        key: wa::MessageKey,
        duration: PinDuration,
    ) -> Result<(), anyhow::Error> {
        self.send_pin(
            chat,
            key,
            wa::message::pin_in_chat_message::Type::PinForAll,
            duration.as_secs(),
        )
        .await
    }

    /// Unpin a previously pinned message.
    pub async fn unpin_message(&self, chat: Jid, key: wa::MessageKey) -> Result<(), anyhow::Error> {
        self.send_pin(
            chat,
            key,
            wa::message::pin_in_chat_message::Type::UnpinForAll,
            0,
        )
        .await
    }

    async fn send_pin(
        &self,
        chat: Jid,
        key: wa::MessageKey,
        pin_type: wa::message::pin_in_chat_message::Type,
        duration_secs: u32,
    ) -> Result<(), anyhow::Error> {
        let message = wa::Message {
            pin_in_chat_message: Some(wa::message::PinInChatMessage {
                key: Some(key),
                r#type: Some(pin_type as i32),
                sender_timestamp_ms: Some(wacore::time::now_millis()),
            }),
            message_context_info: Some(wa::MessageContextInfo {
                message_add_on_duration_in_secs: Some(duration_secs),
                ..Default::default()
            }),
            ..Default::default()
        };

        self.send_message_impl(
            chat,
            &message,
            None,
            false,
            false,
            Some(crate::types::message::EditAttribute::PinInChat),
            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@broadcast reactions fan out pairwise to the author's devices;
        // status posts keep going through send_status_message (owns recipients).
        let (to, is_status_addon) = if to.is_status_broadcast() {
            let author = message
                .reaction_message
                .as_ref()
                .and_then(|rm| rm.key.as_ref())
                .and_then(|k| k.participant.as_ref())
                .and_then(|p| p.parse::<Jid>().ok())
                .filter(|jid| jid.is_pn() || jid.is_lid())
                .ok_or_else(|| {
                    anyhow!(
                        "send_message to status@broadcast requires \
                         reaction_message.key.participant = status author (user JID). \
                         Use client.status() for posting new statuses."
                    )
                })?;
            (author, true)
        } else {
            (to, false)
        };

        // 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>,
            stale_users: Vec<String>,
        }
        let mut skdm_update: Option<SkdmUpdate> = None;
        let mut should_issue_tc_token_after_send = false;
        let mut used_cached_tc_token_key: Option<String> = None;
        let tc_issue_target = to.clone();

        let mut dm_phash: Option<String> = 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 = encryption_jid.to_protocol_address();

            let session_mutex = self.session_lock_for(signal_addr.as_str()).await;
            let _session_guard = session_mutex.lock().await;

            let mut store_adapter = self.signal_adapter().await;

            wacore::send::prepare_peer_stanza(
                &mut store_adapter.session_store,
                &mut store_adapter.identity_store,
                to,
                &signal_addr,
                message,
                request_id,
            )
            .await?
        } else if to.is_group() {
            // Group messages: no client-level lock needed. The encrypt fan-out
            // inside prepare_group_stanza touches a different Signal session
            // per recipient device, so concurrent group sends to the same
            // chat don't race on shared state.
            let mut group_info = self.groups().query_info(&to).await?;

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

            // Store serialized message bytes for retry (lightweight)
            self.add_recent_message(&to, &request_id, 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::store::sender_key_name::SenderKeyName;
                let sender_address = own_sending_jid.to_protocol_address();
                let sender_key_name = SenderKeyName::from_parts(&to_str, sender_address.as_str());

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

                // WA Web posts SenderKeyExpired with `PERIODIC_ROTATION` after
                // a chain advances past a threshold. Captured-js doesn't show
                // the value; 1000 mirrors common Signal hygiene defaults.
                const SENDER_KEY_ROTATION_THRESHOLD: u32 = 1000;
                let needs_rotation = record
                    .and_then(|mut r| r.sender_key_state_mut().ok().cloned())
                    .and_then(|state| state.sender_chain_key().map(|ck| ck.iteration()))
                    .is_some_and(|iter| iter >= SENDER_KEY_ROTATION_THRESHOLD);
                drop(device_guard);

                if needs_rotation {
                    log::info!(
                        "Periodic sender-key rotation for {to} (chain iteration ≥ {SENDER_KEY_ROTATION_THRESHOLD})"
                    );
                    self.signal_cache
                        .delete_sender_key(sender_key_name.cache_key())
                        .await;
                    if let Err(e) = self
                        .persistence_manager
                        .clear_sender_key_devices(&to_str)
                        .await
                    {
                        log::warn!("periodic rotation: clear_sender_key_devices failed: {e}");
                    }
                    self.sender_key_device_cache.invalidate(&to_str).await;
                }

                force_key_distribution || !key_exists || needs_rotation
            };

            let mut store_adapter = self.signal_adapter_from(device_store_arc.clone());

            let mut stores = store_adapter.as_signal_stores();

            // Determine which devices need SKDM distribution using the unified
            // per-device sender key map (matches WA Web's participant.senderKey Map).
            let skdm_target_devices: Option<Vec<Jid>> = if force_skdm {
                None
            } else {
                self.resolve_skdm_targets(&to_str, &group_info, &own_sending_jid)
                    .await
            };

            match wacore::send::prepare_group_stanza(
                &*self.runtime,
                &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(prepared) => {
                    skdm_update = Some(SkdmUpdate {
                        to_str: to_str.clone(),
                        devices: prepared.skdm_devices,
                        stale_users: prepared.stale_device_users,
                    });
                    prepared.node
                }
                Err(e) => {
                    if let Some(SignalProtocolError::NoSenderKeyState(_)) =
                        e.downcast_ref::<SignalProtocolError>()
                    {
                        log::warn!("No sender key for group {}, forcing distribution.", to);

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

                        let mut store_adapter_retry =
                            self.signal_adapter_from(device_store_arc.clone());
                        let mut stores_retry = store_adapter_retry.as_signal_stores();

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

                        skdm_update = Some(SkdmUpdate {
                            to_str,
                            devices: retry_prepared.skdm_devices,
                            stale_users: retry_prepared.stale_device_users,
                        });
                        retry_prepared.node
                    } else {
                        return Err(e);
                    }
                }
            }
        } else {
            // Per-device locking to match decrypt path (message.rs:684),
            // preventing ratchet desync on concurrent send/receive.

            // Status reaction retries arrive with `from=status@broadcast`;
            // cache under the broadcast chat so take_recent_message hits.
            if is_status_addon {
                self.add_recent_message(&Jid::status_broadcast(), &request_id, message)
                    .await;
            } else {
                self.add_recent_message(&to, &request_id, message).await;
            }

            let device_snapshot = self.persistence_manager.get_device_snapshot().await;
            let own_jid = device_snapshot
                .pn
                .as_ref()
                .ok_or(crate::client::ClientError::NotLoggedIn)?;

            // PN→LID mapping (WA Web: ManagePhoneNumberMappingJob)
            if to.is_pn() && self.lid_pn_cache.get_current_lid(&to.user).await.is_none() {
                let sid = self.generate_request_id();
                let spec = wacore::iq::usync::LidQuerySpec::new(vec![to.to_non_ad()], sid);
                // Best-effort: WA Web also catches and warns on failure
                match self.execute(spec).await {
                    Ok(resp) => {
                        for mapping in &resp.lid_mappings {
                            if let Err(e) = self
                                .add_lid_pn_mapping(
                                    &mapping.lid,
                                    &mapping.phone_number,
                                    crate::lid_pn_cache::LearningSource::Usync,
                                )
                                .await
                            {
                                log::warn!(
                                    "Failed to persist LID mapping {} -> {}: {e:?}",
                                    mapping.phone_number,
                                    mapping.lid
                                );
                            }
                        }
                    }
                    Err(e) => {
                        log::warn!("LID query failed for {}, falling back to PN: {e:?}", to);
                    }
                }
            }

            // DM fanout: all known recipient devices + own companions.
            // WAWebSendUserMsgJob reads local device table only on the send
            // path; WAWebDBDeviceListFanout excludes hosted devices.
            let recipient_bare = self.resolve_encryption_jid(&to).await.to_non_ad();

            // Local registry first; network warm only on miss to avoid
            // unnecessary LID-migration side effects from get_user_devices
            let mut recipient_cached = self.get_devices_from_registry(&recipient_bare).await;
            if recipient_cached.is_none() {
                let _ = self.get_user_devices(std::slice::from_ref(&to)).await;
                recipient_cached = self.get_devices_from_registry(&recipient_bare).await;
            }

            let mut own_cached = self.get_devices_from_registry(own_jid).await;
            if own_cached.is_none() {
                let _ = self.get_user_devices(std::slice::from_ref(own_jid)).await;
                own_cached = self.get_devices_from_registry(own_jid).await;
            }

            // Build device list, filter hosted in-place, reuse Vecs
            let mut all_dm_jids = match recipient_cached {
                Some(mut devices) => {
                    devices.retain(|j| !j.is_hosted());
                    devices
                }
                // No record at all — bare JID, server handles fanout
                None => vec![recipient_bare],
            };

            if let Some(mut own_devices) = own_cached {
                own_devices.retain(|j| !j.is_hosted());
                all_dm_jids.append(&mut own_devices);
            }

            // Exclude exact sender device (WA Web: isMeDevice in getFanOutList)
            // so ensure_e2e_sessions never creates a self-session
            let own_lid = device_snapshot.lid.as_ref();
            all_dm_jids.retain(|j| {
                let is_sender = (j.is_same_user_as(own_jid) && j.device == own_jid.device)
                    || own_lid.is_some_and(|lid| j.is_same_user_as(lid) && j.device == lid.device);
                !is_sender
            });

            // Dedup for self-DMs: recipient and own device lists overlap when
            // sending to own account. `participant_list_hash` sorts internally,
            // so reordering here is safe.
            wacore::types::jid::sort_dedup_by_device(&mut all_dm_jids);

            self.ensure_e2e_sessions(&all_dm_jids).await?;

            let mut extra_stanza_nodes = extra_stanza_nodes;
            // tctoken applies to 1:1 chats; status reactions share the fanout
            // path but WA Web does not attach tctokens to them.
            if !to.is_group() && !to.is_newsletter() && !is_status_addon {
                let (should_issue_after_send, cached_token_key) = self
                    .maybe_include_tc_token(&to, &mut extra_stanza_nodes)
                    .await;
                should_issue_tc_token_after_send = should_issue_after_send;
                if should_issue_after_send {
                    used_cached_tc_token_key = cached_token_key;
                }
            }
            if should_issue_tc_token_after_send {
                debug!(target: "Client/TcToken", "Scheduled tc token issuance after send for {}", to);
            }

            let lock_jids = self.build_session_lock_keys(&all_dm_jids).await;
            let _session_mutexes = self.session_mutexes_for(&lock_jids).await;
            let mut _session_guards = Vec::with_capacity(_session_mutexes.len());
            for mutex in &_session_mutexes {
                _session_guards.push(mutex.lock().await);
            }

            let mut store_adapter = self.signal_adapter().await;

            let mut stores = store_adapter.as_signal_stores();

            let prepared = wacore::send::prepare_dm_stanza(
                &*self.runtime,
                &mut stores,
                self,
                own_jid,
                device_snapshot.lid.as_ref(),
                device_snapshot.account.as_ref(),
                to,
                message,
                request_id,
                edit,
                &extra_stanza_nodes,
                all_dm_jids,
            )
            .await?;
            dm_phash = prepared.phash;
            prepared.node
        };

        let ack = if let Some(phash) = dm_phash
            && let Some(msg_id) = stanza_to_send
                .attrs()
                .optional_string("id")
                .map(|s| s.into_owned())
        {
            let rx = self.register_ack_waiter(&msg_id).await;
            Some((rx, phash, msg_id))
        } else {
            None
        };

        // Server expects the outer `to` as the broadcast chat even though
        // encryption targeted the author's devices (mirrors incoming `from`).
        let mut stanza_to_send = stanza_to_send;
        if is_status_addon {
            stanza_to_send.attrs.insert("to", Jid::status_broadcast());
        }

        if let Err(e) = self.send_node(stanza_to_send).await {
            if let Some((_, _, ref msg_id)) = ack {
                self.response_waiters.lock().await.remove(msg_id);
            }
            return Err(e.into());
        }

        if let Some((rx, phash, msg_id)) = ack {
            // Group sends also invalidate group cache on mismatch — server's
            // participant set diverged, the next send needs a fresh query.
            let invalidate_group = tc_issue_target.is_group();
            self.spawn_phash_validation(
                rx,
                phash,
                tc_issue_target.clone(),
                invalidate_group,
                msg_id,
            );
        }

        if let Some(update) = skdm_update {
            self.update_sender_key_devices(&update.to_str, &update.devices)
                .await;
            for user in &update.stale_users {
                self.invalidate_device_cache(user).await;
            }
        }

        // Flush cached Signal state to DB after encryption
        self.flush_signal_cache_logged("send_message_impl", None)
            .await;

        // Issue new tc token after send if a bucket boundary was crossed.
        // Fire-and-forget so send_message returns without waiting for the IQ
        if should_issue_tc_token_after_send {
            if let Some(client) = self.self_weak.get().and_then(|w| w.upgrade()) {
                let target = tc_issue_target;
                let cached_key = used_cached_tc_token_key;
                self.runtime
                    .spawn(Box::pin(async move {
                        let issued_ok = client.issue_tc_token_after_send(&target).await;
                        if issued_ok && let Some(token_key) = cached_key {
                            client.mark_tc_token_used_after_send(&token_key).await;
                        }
                    }))
                    .detach();
            } else {
                log::debug!(target: "Client/TcToken", "Skipping fire-and-forget issuance: client dropped");
            }
        }

        Ok(())
    }

    /// Look up and include a privacy token in outgoing 1:1 message stanza nodes.
    ///
    /// Follows WA Web's fallback chain (MsgCreateFanoutStanza.js):
    ///   1. tctoken — from stored trusted contact token (if valid, non-expired)
    ///   2. cstoken — HMAC-SHA256(nct_salt, recipient_lid) fallback for first-contact
    ///   3. No token — message sent without token (server may return 463)
    ///
    /// Returns whether we should issue a new tc token after send, and the cache key
    /// of the attached valid tc token when that token should be marked as used.
    async fn maybe_include_tc_token(
        &self,
        to: &Jid,
        extra_nodes: &mut Vec<Node>,
    ) -> (bool, Option<String>) {
        use wacore::iq::props::config_codes;
        use wacore::iq::tctoken::{
            build_cs_token_node, build_tc_token_node, compute_cs_token, is_tc_token_expired_with,
            should_send_new_tc_token_with,
        };

        // 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 (false, None);
        }

        // Bots and status broadcast don't participate in the privacy token system
        if to.is_bot() || to.is_status_broadcast() {
            return (false, None);
        }

        // Resolve the destination to a LID user string once — reused for
        // tctoken lookup, issuance, and cstoken HMAC input.
        let cached_lid = if to.is_lid() {
            None
        } else {
            self.lid_pn_cache.get_current_lid(&to.user).await
        };
        let resolved_lid_user: Option<&str> = if to.is_lid() {
            Some(&to.user)
        } else {
            cached_lid.as_deref()
        };
        let token_jid: &str = resolved_lid_user.unwrap_or(&to.user);

        let backend = self.persistence_manager.backend();
        let tc_config = self.tc_token_config().await;

        // Look up existing tctoken
        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);
                None
            }
        };

        // Issuance scheduling is independent of the AB prop — WA Web's sendTcToken
        // in MsgJob.js fires regardless of whether a token was attached to the stanza
        let should_issue_after_send = should_send_new_tc_token_with(
            existing.as_ref().and_then(|entry| entry.sender_timestamp),
            &tc_config,
        );

        // AB prop gates stanza inclusion only (not issuance scheduling)
        let token_send_enabled = self
            .ab_props
            .is_enabled_or(config_codes::PRIVACY_TOKEN_ON_ALL_1_ON_1_MESSAGES, false)
            .await;

        if token_send_enabled {
            match existing {
                Some(ref entry)
                    if !is_tc_token_expired_with(entry.token_timestamp, &tc_config)
                        && !entry.token.is_empty() =>
                {
                    extra_nodes.push(build_tc_token_node(&entry.token));
                    return (should_issue_after_send, Some(token_jid.to_string()));
                }
                _ => {
                    // cstoken fallback — gated by wa_nct_token_send_enabled
                    let nct_send_enabled = self
                        .ab_props
                        .is_enabled_or(config_codes::NCT_TOKEN_SEND_ENABLED, false)
                        .await;

                    if nct_send_enabled
                        && let Some(salt) = &snapshot.nct_salt
                        && let Some(lid_user) = &resolved_lid_user
                    {
                        // HMAC input is "user@lid" (account LID without device suffix),
                        // matching WA Web's accountLid.toString()
                        let recipient_lid =
                            wacore_binary::Jid::new(*lid_user, Server::Lid).to_string();
                        let cs_token = compute_cs_token(salt, &recipient_lid);
                        extra_nodes.push(build_cs_token_node(&cs_token));
                        log::debug!(target: "Client/CsToken", "Attached cstoken for {} (NCT fallback)", to);
                    } else {
                        log::debug!(target: "Client/CsToken", "No tctoken or NCT salt/LID available for {}", to);
                    }
                }
            }
        }

        (should_issue_after_send, None)
    }

    /// Returns `true` if the issuance IQ succeeded.
    async fn issue_tc_token_after_send(&self, to: &Jid) -> bool {
        use wacore::iq::tctoken::IssuePrivacyTokensSpec;

        // Bots and status broadcast don't participate in the privacy token system
        if to.is_bot() || to.is_status_broadcast() {
            return false;
        }

        let issuance_jid = self.resolve_issuance_jid(to).await;
        let Ok(response) = self
            .execute(IssuePrivacyTokensSpec::new(std::slice::from_ref(
                &issuance_jid,
            )))
            .await
        else {
            log::debug!(target: "Client/TcToken", "Failed to issue tc_token for {}", issuance_jid);
            return false;
        };

        self.store_issued_tc_tokens(&response.tokens).await
    }

    /// Returns true if at least one token was persisted.
    pub(crate) async fn store_issued_tc_tokens(
        &self,
        tokens: &[wacore::iq::tctoken::ReceivedTcToken],
    ) -> bool {
        use wacore::store::traits::TcTokenEntry;

        if tokens.is_empty() {
            return false;
        }

        let backend = self.persistence_manager.backend();
        let now = wacore::time::now_secs();
        let mut any_stored = false;
        for received in tokens {
            if received.token.is_empty() {
                log::warn!(target: "Client/TcToken", "Server returned empty tc_token for {}, skipping", received.jid);
                continue;
            }

            let entry = TcTokenEntry {
                token: received.token.clone(),
                token_timestamp: received.timestamp,
                sender_timestamp: Some(now),
            };

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

    /// Variant of [`store_issued_tc_tokens`] that preserves the original
    /// sender_timestamp for identity-change re-issuance (bucket continuity).
    async fn store_issued_tc_tokens_with_sender_ts(
        &self,
        tokens: &[wacore::iq::tctoken::ReceivedTcToken],
        sender_ts: i64,
    ) {
        use wacore::store::traits::TcTokenEntry;

        let backend = self.persistence_manager.backend();
        for received in tokens {
            if received.token.is_empty() {
                continue;
            }
            let entry = TcTokenEntry {
                token: received.token.clone(),
                token_timestamp: received.timestamp,
                sender_timestamp: Some(sender_ts),
            };
            if let Err(e) = backend.put_tc_token(&received.jid.user, &entry).await {
                log::warn!(target: "Client/TcToken", "Failed to store re-issued tc_token: {e}");
            }
        }
    }

    async fn mark_tc_token_used_after_send(&self, token_key: &str) {
        use wacore::store::traits::TcTokenEntry;

        let backend = self.persistence_manager.backend();
        let existing = match backend.get_tc_token(token_key).await {
            Ok(entry) => entry,
            Err(e) => {
                log::warn!(target: "Client/TcToken", "Failed to reload tc_token for {}: {e}", token_key);
                return;
            }
        };

        let Some(entry) = existing else {
            return;
        };
        if entry.token.is_empty() {
            return;
        }

        let updated_entry = TcTokenEntry {
            sender_timestamp: Some(wacore::time::now_secs()),
            ..entry
        };
        if let Err(e) = backend.put_tc_token(token_key, &updated_entry).await {
            log::warn!(target: "Client/TcToken", "Failed to update sender_timestamp for {}: {e}", token_key);
        }
    }

    /// Re-issue tctoken after a contact's device identity changes.
    /// Only re-issues if we previously sent a token (sender_timestamp valid).
    /// Uses session_locks to deduplicate concurrent spawns for the same sender.
    pub(crate) async fn reissue_tc_token_after_identity_change(&self, sender: &Jid) {
        use wacore::iq::tctoken::{IssuePrivacyTokensSpec, is_sender_tc_token_expired};

        // Dedup via session_locks — bare JID won't collide with protocol addresses ("user:device")
        let bare = sender.to_non_ad().to_string();
        let mutex = self.session_lock_for(&bare).await;
        let Some(_guard) = mutex.try_lock() else {
            return;
        };

        let resolved_lid = if sender.is_lid() {
            None
        } else {
            self.lid_pn_cache.get_current_lid(&sender.user).await
        };
        let token_jid: &str = resolved_lid.as_deref().unwrap_or(&sender.user);

        let backend = self.persistence_manager.backend();
        let entry = match backend.get_tc_token(token_jid).await {
            Ok(Some(e)) => e,
            _ => return,
        };

        let Some(sender_ts) = entry.sender_timestamp else {
            return;
        };

        // Sender-side expiration (may use different bucket config than receiver)
        let tc_config = self.tc_token_config().await;
        if is_sender_tc_token_expired(sender_ts, &tc_config) {
            return;
        }

        // Use stored sender_ts so the bucket window isn't advanced
        let issuance_jid = self.resolve_issuance_jid(sender).await;
        match self
            .execute(IssuePrivacyTokensSpec::with_timestamp(
                std::slice::from_ref(&issuance_jid),
                sender_ts,
            ))
            .await
        {
            Ok(response) => {
                // Keep original sender_ts so the bucket window isn't advanced
                self.store_issued_tc_tokens_with_sender_ts(&response.tokens, sender_ts)
                    .await;
                log::debug!(
                    target: "Client/TcToken",
                    "Re-issued tctoken after identity change for {}",
                    sender
                );
            }
            Err(e) => {
                log::debug!(
                    target: "Client/TcToken",
                    "Failed to re-issue tctoken after identity change for {}: {e}",
                    sender
                );
            }
        }
    }

    /// 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_with;

        let resolved_lid = if jid.is_lid() {
            None
        } else {
            self.lid_pn_cache.get_current_lid(&jid.user).await
        };
        let token_jid: &str = resolved_lid.as_deref().unwrap_or(&jid.user);

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

    /// Build sorted, deduplicated per-device session lock keys.
    /// INVARIANT: Keys are sorted to prevent deadlocks when acquiring multiple
    /// session locks (e.g. DM sends that encrypt for recipient + own devices).
    /// Resolve encryption JIDs and sort for deadlock-free lock acquisition.
    pub(crate) async fn build_session_lock_keys(&self, device_jids: &[Jid]) -> Vec<Jid> {
        let mut keys: Vec<Jid> = Vec::with_capacity(device_jids.len());
        for jid in device_jids {
            keys.push(self.resolve_encryption_jid(jid).await);
        }
        keys.sort_unstable_by(wacore::types::jid::cmp_for_lock_order);
        keys.dedup_by(|a, b| wacore::types::jid::cmp_for_lock_order(a, b).is_eq());
        keys
    }

    /// Fetch per-device session mutexes in deadlock-free order.
    pub(crate) async fn session_mutexes_for(
        &self,
        jids: &[Jid],
    ) -> Vec<std::sync::Arc<async_lock::Mutex<()>>> {
        let mut mutexes = Vec::with_capacity(jids.len());
        let mut buf = wacore::types::jid::make_address_buffer();
        for jid in jids {
            wacore::types::jid::write_protocol_address_to(jid, &mut buf);
            mutexes.push(self.session_lock_for(&buf).await);
        }
        mutexes
    }

    /// Build tctoken timing config from AB props, falling back to defaults.
    pub(crate) async fn tc_token_config(&self) -> wacore::iq::tctoken::TcTokenConfig {
        use wacore::iq::props::config_codes;
        use wacore::iq::tctoken::{TC_TOKEN_BUCKET_DURATION, TC_TOKEN_NUM_BUCKETS, TcTokenConfig};

        TcTokenConfig {
            bucket_duration: self
                .ab_props
                .get_int(config_codes::TCTOKEN_DURATION, TC_TOKEN_BUCKET_DURATION)
                .await,
            num_buckets: self
                .ab_props
                .get_int(config_codes::TCTOKEN_NUM_BUCKETS, TC_TOKEN_NUM_BUCKETS)
                .await,
            sender_bucket_duration: self
                .ab_props
                .get_int(
                    config_codes::TCTOKEN_DURATION_SENDER,
                    TC_TOKEN_BUCKET_DURATION,
                )
                .await,
            sender_num_buckets: self
                .ab_props
                .get_int(
                    config_codes::TCTOKEN_NUM_BUCKETS_SENDER,
                    TC_TOKEN_NUM_BUCKETS,
                )
                .await,
        }
        .clamped()
    }

    /// 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.to_non_ad();
        }

        if let Some(lid_user) = self.lid_pn_cache.get_current_lid(&jid.user).await {
            Jid::new(&lid_user, Server::Lid)
        } else {
            jid.to_non_ad()
        }
    }

    /// Resolve the target JID for privacy token issuance.
    /// Gated by `lid_trusted_token_issue_to_lid` — LID when true, PN when false.
    async fn resolve_issuance_jid(&self, jid: &Jid) -> Jid {
        use wacore::iq::props::config_codes;

        // Default true: issue to LID by default (safer — server accepts both)
        let issue_to_lid = self
            .ab_props
            .is_enabled_or(config_codes::LID_TRUSTED_TOKEN_ISSUE_TO_LID, true)
            .await;

        let resolved = if issue_to_lid {
            self.resolve_to_lid_jid(jid).await
        } else if jid.is_lid() {
            if let Some(pn) = self.lid_pn_cache.get_phone_number(&jid.user).await {
                Jid::new(&pn, Server::Pn)
            } else {
                jid.to_non_ad()
            }
        } else {
            jid.to_non_ad()
        };
        // Issuance targets bare account JIDs, not device-scoped ones
        resolved.to_non_ad()
    }
}

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

    #[tokio::test]
    async fn send_message_to_status_without_reaction_errors() {
        let client = crate::test_utils::create_test_client().await;
        let to = Jid::status_broadcast();
        let err = client
            .send_message(
                to,
                wa::Message {
                    conversation: Some("hi".into()),
                    ..Default::default()
                },
            )
            .await
            .expect_err("status@broadcast without reaction must error");
        let msg = format!("{err}");
        assert!(
            msg.contains("reaction_message") || msg.contains("status"),
            "unexpected error: {msg}"
        );
    }

    #[tokio::test]
    async fn send_message_to_status_reaction_rejects_non_user_participant() {
        let client = crate::test_utils::create_test_client().await;
        let to = Jid::status_broadcast();
        let err = client
            .send_message(
                to,
                wa::Message {
                    reaction_message: Some(wa::message::ReactionMessage {
                        key: Some(wa::MessageKey {
                            remote_jid: Some("status@broadcast".into()),
                            from_me: Some(false),
                            id: Some("ORIGID".into()),
                            participant: Some("120363040237990503@g.us".into()),
                        }),
                        text: Some("❤️".into()),
                        sender_timestamp_ms: Some(1),
                        ..Default::default()
                    }),
                    ..Default::default()
                },
            )
            .await
            .expect_err("group JID as participant must error");
        assert!(
            format!("{err}").contains("user JID"),
            "expected user-JID error, got: {err}"
        );
    }

    #[tokio::test]
    async fn send_message_to_status_reaction_without_participant_errors() {
        let client = crate::test_utils::create_test_client().await;
        let to = Jid::status_broadcast();
        let err = client
            .send_message(
                to,
                wa::Message {
                    reaction_message: Some(wa::message::ReactionMessage {
                        key: Some(wa::MessageKey {
                            remote_jid: Some("status@broadcast".into()),
                            from_me: Some(false),
                            id: Some("ORIGID".into()),
                            participant: None,
                        }),
                        text: Some("❤️".into()),
                        sender_timestamp_ms: Some(1),
                        ..Default::default()
                    }),
                    ..Default::default()
                },
            )
            .await
            .expect_err("reaction without key.participant must error");
        assert!(
            format!("{err}").contains("participant"),
            "expected participant error, got: {err}"
        );
    }

    #[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 = build_revoke_message(&to, from_me, message_id.clone(), participant);

        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 =
            build_revoke_message(&to, from_me, message_id.clone(), participant.clone());

        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 empty_sender_key_device_map_marks_all_devices_for_skdm() {
        use crate::sender_key_device_cache::SenderKeyDeviceMap;

        let map = SenderKeyDeviceMap::from_db_rows(&[]);
        assert_eq!(map.device_has_key("271060335329480", 0), None);
        assert!(!map.is_user_forgotten("271060335329480"));

        let all_resolved_devices: Vec<Jid> = [
            "271060335329480@lid",
            "77610646245392@lid",
            "276661023027320:5@lid",
        ]
        .into_iter()
        .map(|s| Jid::from_str(s).unwrap())
        .collect();

        let needs_skdm: Vec<&Jid> = all_resolved_devices
            .iter()
            .filter(|device| {
                !map.device_has_key(&device.user, device.device)
                    .unwrap_or(false)
                    || map.is_user_forgotten(&device.user)
            })
            .collect();

        assert_eq!(needs_skdm.len(), all_resolved_devices.len());
    }

    /// Fails if the empty-cache early-exit is reintroduced.
    #[tokio::test]
    async fn resolve_skdm_targets_distributes_when_cache_empty_but_devices_known() {
        use wacore::client::context::GroupInfo;
        use wacore::store::traits::{DeviceInfo, DeviceListRecord};
        use wacore::types::message::AddressingMode;

        let client = crate::test_utils::create_test_client().await;
        let group_jid = "120363161500776365@g.us";
        let own_lid = Jid::from_str("193832511623409:13@lid").unwrap();

        let participant_users = ["271060335329480", "77610646245392", "276661023027320"];

        // Pre-populate so `resolve_devices` succeeds without a transport.
        for user in &participant_users {
            let record = DeviceListRecord {
                user: (*user).into(),
                devices: vec![DeviceInfo {
                    device_id: 0,
                    key_index: None,
                }],
                timestamp: wacore::time::now_secs(),
                phash: None,
                raw_id: None,
            };
            client
                .device_registry_cache
                .insert((*user).into(), record)
                .await;
        }

        let participants: Vec<Jid> = participant_users
            .iter()
            .map(|u| Jid::from_str(&format!("{u}@lid")).unwrap())
            .collect();

        let group_info = GroupInfo::new(participants.clone(), AddressingMode::Lid);

        let result = client
            .resolve_skdm_targets(group_jid, &group_info, &own_lid)
            .await
            .expect("None means the empty-cache early-exit is back");

        assert_eq!(result.len(), participants.len());
        for user in &participant_users {
            assert!(result.iter().any(|j| j.user == *user));
        }
    }

    #[test]
    fn single_forgotten_row_keeps_full_distribution() {
        use crate::sender_key_device_cache::SenderKeyDeviceMap;

        let map = SenderKeyDeviceMap::from_db_rows(&[("271060335329480@lid".to_string(), false)]);
        assert_eq!(map.device_has_key("271060335329480", 0), Some(false));
        assert!(map.is_user_forgotten("271060335329480"));

        let all_resolved_devices: Vec<Jid> = [
            "271060335329480@lid",
            "77610646245392@lid",
            "276661023027320:5@lid",
        ]
        .into_iter()
        .map(|s| Jid::from_str(s).unwrap())
        .collect();

        let needs_skdm: Vec<&Jid> = all_resolved_devices
            .iter()
            .filter(|device| {
                !map.device_has_key(&device.user, device.device)
                    .unwrap_or(false)
                    || map.is_user_forgotten(&device.user)
            })
            .collect();

        assert_eq!(
            needs_skdm.len(),
            3,
            "after retry inserts one row, ALL devices correctly flagged for SKDM \
             (this is what unblocks redistribution on the SECOND message)"
        );
    }

    #[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);
    }

    mod infer_stanza {
        use super::*;

        #[test]
        fn regular_message_returns_none() {
            let msg = wa::Message {
                conversation: Some("hello".into()),
                ..Default::default()
            };
            let (edit, node) = infer_stanza_metadata(&msg);
            assert!(edit.is_none());
            assert!(node.is_none());
        }

        #[test]
        fn pin_returns_edit_attribute() {
            let msg = wa::Message {
                pin_in_chat_message: Some(wa::message::PinInChatMessage::default()),
                ..Default::default()
            };
            let (edit, node) = infer_stanza_metadata(&msg);
            assert_eq!(edit, Some(EditAttribute::PinInChat));
            assert!(node.is_none());
        }

        #[test]
        fn poll_creation_v3_returns_meta_node() {
            let msg = wa::Message {
                poll_creation_message_v3: Some(Box::default()),
                ..Default::default()
            };
            let (edit, node) = infer_stanza_metadata(&msg);
            assert!(edit.is_none());
            let node = node.expect("should have meta node");
            assert_eq!(node.tag, "meta");
            let mut attrs = node.attrs();
            assert_eq!(
                attrs.optional_string("polltype").unwrap().as_ref(),
                "creation"
            );
        }

        #[test]
        fn event_returns_meta_node() {
            let msg = wa::Message {
                event_message: Some(Box::default()),
                ..Default::default()
            };
            let (edit, node) = infer_stanza_metadata(&msg);
            assert!(edit.is_none());
            let node = node.expect("should have meta node");
            assert_eq!(node.tag, "meta");
            let mut attrs = node.attrs();
            assert_eq!(
                attrs.optional_string("event_type").unwrap().as_ref(),
                "creation"
            );
        }

        #[test]
        fn empty_message_returns_none() {
            let (edit, node) = infer_stanza_metadata(&wa::Message::default());
            assert!(edit.is_none());
            assert!(node.is_none());
        }

        #[test]
        fn poll_creation_v1_returns_meta_node() {
            let msg = wa::Message {
                poll_creation_message: Some(Box::default()),
                ..Default::default()
            };
            let (edit, node) = infer_stanza_metadata(&msg);
            assert!(edit.is_none());
            let node = node.expect("should have meta node");
            assert_eq!(node.tag, "meta");
            let mut attrs = node.attrs();
            assert_eq!(
                attrs.optional_string("polltype").unwrap().as_ref(),
                "creation"
            );
        }

        #[test]
        fn poll_creation_v2_returns_meta_node() {
            let msg = wa::Message {
                poll_creation_message_v2: Some(Box::default()),
                ..Default::default()
            };
            let (edit, node) = infer_stanza_metadata(&msg);
            assert!(edit.is_none());
            let node = node.expect("should have meta node");
            assert_eq!(node.tag, "meta");
            let mut attrs = node.attrs();
            assert_eq!(
                attrs.optional_string("polltype").unwrap().as_ref(),
                "creation"
            );
        }

        #[test]
        fn poll_vote_returns_meta_node() {
            let msg = wa::Message {
                poll_update_message: Some(wa::message::PollUpdateMessage {
                    vote: Some(wa::message::PollEncValue::default()),
                    ..Default::default()
                }),
                ..Default::default()
            };
            let (edit, node) = infer_stanza_metadata(&msg);
            assert!(edit.is_none());
            let node = node.expect("should have meta node");
            assert_eq!(node.tag, "meta");
            let mut attrs = node.attrs();
            assert_eq!(attrs.optional_string("polltype").unwrap().as_ref(), "vote");
        }

        #[test]
        fn event_response_returns_meta_node() {
            let msg = wa::Message {
                enc_event_response_message: Some(Default::default()),
                ..Default::default()
            };
            let (edit, node) = infer_stanza_metadata(&msg);
            assert!(edit.is_none());
            let node = node.expect("should have meta node");
            assert_eq!(node.tag, "meta");
            let mut attrs = node.attrs();
            assert_eq!(
                attrs.optional_string("event_type").unwrap().as_ref(),
                "response"
            );
        }

        #[test]
        fn poll_update_without_vote_returns_none() {
            let msg = wa::Message {
                poll_update_message: Some(wa::message::PollUpdateMessage {
                    vote: None,
                    ..Default::default()
                }),
                ..Default::default()
            };
            let (edit, node) = infer_stanza_metadata(&msg);
            assert!(edit.is_none());
            assert!(node.is_none());
        }
    }

    mod infer_biz {
        use super::*;
        use wa::message::interactive_message::{
            self, NativeFlowMessage, native_flow_message::NativeFlowButton,
        };

        fn msg_with_native_flow(button_name: &str) -> wa::Message {
            wa::Message {
                document_with_caption_message: Some(Box::new(wa::message::FutureProofMessage {
                    message: Some(Box::new(wa::Message {
                        interactive_message: Some(Box::new(wa::message::InteractiveMessage {
                            interactive_message: Some(
                                interactive_message::InteractiveMessage::NativeFlowMessage(
                                    NativeFlowMessage {
                                        buttons: vec![NativeFlowButton {
                                            name: Some(button_name.to_string()),
                                            button_params_json: None,
                                        }],
                                        message_version: Some(1),
                                        message_params_json: None,
                                    },
                                ),
                            ),
                            ..Default::default()
                        })),
                        ..Default::default()
                    })),
                })),
                ..Default::default()
            }
        }

        fn assert_biz_node(node: &Node, expected_flow_name: &str) {
            assert_eq!(node.tag, "biz");
            assert!(
                node.attrs().optional_string("native_flow_name").is_none(),
                "should NOT use simple attribute form"
            );
            let interactive = node.get_optional_child("interactive").unwrap();
            let mut attrs = interactive.attrs();
            assert_eq!(
                attrs.optional_string("type").unwrap().as_ref(),
                "native_flow"
            );
            assert_eq!(attrs.optional_string("v").unwrap().as_ref(), "1");
            let nf = interactive.get_optional_child("native_flow").unwrap();
            let mut nf_attrs = nf.attrs();
            assert_eq!(
                nf_attrs.optional_string("name").unwrap().as_ref(),
                expected_flow_name
            );
        }

        #[test]
        fn all_button_types_use_nested_structure() {
            for (button, expected_flow) in [
                ("cta_url", "cta_url"),
                ("payment_info", "payment_info"),
                ("review_and_pay", "order_details"),
                ("cta_catalog", "cta_catalog"),
                ("mpm", "mpm"),
                ("quick_reply", "quick_reply"),
            ] {
                let node = infer_biz_node(&msg_with_native_flow(button))
                    .unwrap_or_else(|| panic!("{button} should produce biz node"));
                assert_biz_node(&node, expected_flow);
            }
        }

        #[test]
        fn no_interactive_returns_none() {
            let msg = wa::Message {
                conversation: Some("hello".into()),
                ..Default::default()
            };
            assert!(infer_biz_node(&msg).is_none());
        }

        #[test]
        fn interactive_without_native_flow_returns_none() {
            let msg = wa::Message {
                interactive_message: Some(Box::new(wa::message::InteractiveMessage {
                    interactive_message: Some(
                        interactive_message::InteractiveMessage::CollectionMessage(
                            Default::default(),
                        ),
                    ),
                    ..Default::default()
                })),
                ..Default::default()
            };
            assert!(infer_biz_node(&msg).is_none());
        }

        #[test]
        fn native_flow_without_buttons_returns_none() {
            let msg = wa::Message {
                interactive_message: Some(Box::new(wa::message::InteractiveMessage {
                    interactive_message: Some(
                        interactive_message::InteractiveMessage::NativeFlowMessage(
                            NativeFlowMessage {
                                buttons: vec![],
                                message_version: Some(1),
                                message_params_json: None,
                            },
                        ),
                    ),
                    ..Default::default()
                })),
                ..Default::default()
            };
            assert!(infer_biz_node(&msg).is_none());
        }

        #[test]
        fn direct_interactive_message_without_wrapper() {
            let msg = wa::Message {
                interactive_message: Some(Box::new(wa::message::InteractiveMessage {
                    interactive_message: Some(
                        interactive_message::InteractiveMessage::NativeFlowMessage(
                            NativeFlowMessage {
                                buttons: vec![NativeFlowButton {
                                    name: Some("cta_url".to_string()),
                                    button_params_json: None,
                                }],
                                message_version: Some(1),
                                message_params_json: None,
                            },
                        ),
                    ),
                    ..Default::default()
                })),
                ..Default::default()
            };
            let node = infer_biz_node(&msg).unwrap();
            assert_biz_node(&node, "cta_url");
        }
    }

    /// Regression tests for #462: send path session lock keys must match decrypt path.
    mod session_lock_regression {
        use super::*;

        #[tokio::test]
        async fn per_device_lock_keys_cover_all_devices() {
            let client = crate::test_utils::create_test_client().await;

            let devices: Vec<Jid> = [
                "100000012345678@lid",
                "100000012345678:5@lid",
                "100000012345678:33@lid",
            ]
            .iter()
            .map(|s| Jid::from_str(s).unwrap())
            .collect();

            // Uses the production helper (resolve_encryption_jid + sort + dedup)
            let send_lock_keys = client.build_session_lock_keys(&devices).await;

            assert_eq!(send_lock_keys.len(), 3);
            // Sorted by (server, user, device_numeric): 0, 5, 33
            assert_eq!(send_lock_keys[0].device, 0);
            assert_eq!(send_lock_keys[1].device, 5);
            assert_eq!(send_lock_keys[2].device, 33);

            // Send keys must cover every device
            for device_jid in &devices {
                assert!(
                    send_lock_keys.contains(device_jid),
                    "device {device_jid} not in send keys: {send_lock_keys:?}"
                );
            }

            // Bare JID key alone wouldn't protect linked devices
            let bare_key = devices[0].to_protocol_address_string();
            let device5_key = devices[1].to_protocol_address_string();
            assert_ne!(bare_key, device5_key);
        }

        #[tokio::test]
        async fn per_device_lock_serializes_concurrent_session_access() {
            use std::sync::Arc;
            use std::sync::atomic::{AtomicU32, Ordering};

            let session_locks: crate::cache::Cache<String, Arc<async_lock::Mutex<()>>> =
                crate::cache::Cache::builder().max_capacity(100).build();

            let lock_key = "100000012345678:5@lid.0".to_string();
            let access_counter = Arc::new(AtomicU32::new(0));
            let max_concurrent = Arc::new(AtomicU32::new(0));

            let mut handles = Vec::new();
            for _ in 0..10 {
                let locks = session_locks.clone();
                let key = lock_key.clone();
                let counter = access_counter.clone();
                let max = max_concurrent.clone();

                handles.push(tokio::spawn(async move {
                    let mutex: Arc<async_lock::Mutex<()>> = locks
                        .get_with_by_ref(&key, async { Arc::new(async_lock::Mutex::new(())) })
                        .await;
                    // lock_arc() needed: guard must own the Arc since mutex is a local
                    // (production uses lock() with a separate Vec keeping Arcs alive)
                    let _guard = mutex.lock_arc().await;

                    let active = counter.fetch_add(1, Ordering::SeqCst) + 1;
                    max.fetch_max(active, Ordering::SeqCst);
                    tokio::task::yield_now().await;
                    counter.fetch_sub(1, Ordering::SeqCst);
                }));
            }

            for handle in handles {
                handle.await.unwrap();
            }

            assert_eq!(max_concurrent.load(Ordering::SeqCst), 1);
        }

        #[tokio::test]
        async fn different_device_locks_are_independent() {
            use std::sync::Arc;
            use std::sync::atomic::{AtomicU32, Ordering};

            let session_locks: crate::cache::Cache<String, Arc<async_lock::Mutex<()>>> =
                crate::cache::Cache::builder().max_capacity(100).build();

            let max_concurrent = Arc::new(AtomicU32::new(0));
            let counter = Arc::new(AtomicU32::new(0));
            let barrier = Arc::new(tokio::sync::Barrier::new(2));

            let keys = ["100000012345678@lid.0", "100000012345678:5@lid.0"];

            let mut handles = Vec::new();
            for key in keys {
                let locks = session_locks.clone();
                let key = key.to_string();
                let c = counter.clone();
                let m = max_concurrent.clone();
                let b = barrier.clone();

                handles.push(tokio::spawn(async move {
                    let mutex: Arc<async_lock::Mutex<()>> = locks
                        .get_with_by_ref(&key, async { Arc::new(async_lock::Mutex::new(())) })
                        .await;
                    // lock_arc(): same reason as above
                    let _guard = mutex.lock_arc().await;

                    let active = c.fetch_add(1, Ordering::SeqCst) + 1;
                    m.fetch_max(active, Ordering::SeqCst);
                    b.wait().await;
                    c.fetch_sub(1, Ordering::SeqCst);
                }));
            }

            for handle in handles {
                handle.await.unwrap();
            }

            assert_eq!(max_concurrent.load(Ordering::SeqCst), 2);
        }

        /// Regression: 1:1 DM recipient must use bare Signal address matching
        /// the receive path. Starts from device-specific JID and verifies
        /// to_non_ad() normalization produces the correct bare key.
        #[tokio::test]
        async fn dm_recipient_uses_bare_address() {
            let client = crate::test_utils::create_test_client().await;

            // Start from device-specific JID, exercise the production path
            let recipient_device33 = Jid::from_str("100000012345678:33@lid").unwrap();
            let own_device_5 = Jid::from_str("999999999999:5@s.whatsapp.net").unwrap();

            // Same normalization as send_message_impl
            let recipient_bare = client
                .resolve_encryption_jid(&recipient_device33)
                .await
                .to_non_ad();

            let all_dm_jids = vec![recipient_bare.clone(), own_device_5.clone()];
            let lock_jids = client.build_session_lock_keys(&all_dm_jids).await;

            // Recipient lock key must be BARE (device 0), matching decrypt path
            assert_eq!(
                recipient_bare.to_protocol_address_string(),
                "100000012345678@lid.0"
            );
            assert!(lock_jids.contains(&recipient_bare));

            // Own device lock key must be device-specific
            assert!(lock_jids.contains(&own_device_5));

            // Device-specific recipient key must NOT be present
            assert!(
                !lock_jids.contains(&recipient_device33),
                "recipient must NOT use device-specific address"
            );
        }

        /// Verify bare normalization deduplicates multiple recipient devices.
        #[test]
        fn bare_normalization_deduplicates_recipient_devices() {
            let devices: Vec<Jid> = [
                "100000012345678@lid",
                "100000012345678:5@lid",
                "100000012345678:33@lid",
            ]
            .iter()
            .map(|s| Jid::from_str(s).unwrap())
            .collect();

            // All collapse to the same bare JID
            let bare: Vec<Jid> = devices.iter().map(|j| j.to_non_ad()).collect();
            assert!(bare.windows(2).all(|w| w[0] == w[1]));
            assert_eq!(
                bare[0].to_protocol_address_string(),
                "100000012345678@lid.0"
            );
        }
    }
}