//! Axum-based HTTP gateway with proper HTTP/1.1 compliance, body limits, and timeouts.
//!
//! This module replaces the raw TCP implementation with axum for:
//! - Proper HTTP/1.1 parsing and compliance
//! - Content-Length validation (handled by hyper)
//! - Request body size limits (64KB max)
//! - Request timeouts (30s) to prevent slow-loris attacks
//! - Header sanitization (handled by axum/hyper)

use crate::channels::{Channel, SendMessage, WhatsAppChannel};
use crate::config::Config;
use crate::memory::{self, Memory, MemoryCategory};
use crate::providers::{self, Provider};
use crate::runtime;
use crate::security::pairing::{constant_time_eq, is_public_bind, PairingGuard};
use crate::security::SecurityPolicy;
use crate::tools;
use crate::util::truncate_with_ellipsis;
use anyhow::{Context, Result};
use axum::{
    body::Bytes,
    extract::{ConnectInfo, Query, State},
    http::{header, HeaderMap, StatusCode},
    response::{IntoResponse, Json},
    routing::{get, post},
    Router,
};
use parking_lot::Mutex;
use std::collections::HashMap;
use std::net::{IpAddr, SocketAddr};
use std::sync::Arc;
use std::time::{Duration, Instant};
use tower_http::limit::RequestBodyLimitLayer;
use tower_http::timeout::TimeoutLayer;
use uuid::Uuid;

/// Maximum request body size (64KB) — prevents memory exhaustion
pub const MAX_BODY_SIZE: usize = 65_536;
/// Request timeout (30s) — prevents slow-loris attacks
pub const REQUEST_TIMEOUT_SECS: u64 = 30;
/// Sliding window used by gateway rate limiting.
pub const RATE_LIMIT_WINDOW_SECS: u64 = 60;
/// Fallback max distinct client keys tracked in gateway rate limiter.
pub const RATE_LIMIT_MAX_KEYS_DEFAULT: usize = 10_000;
/// Fallback max distinct idempotency keys retained in gateway memory.
pub const IDEMPOTENCY_MAX_KEYS_DEFAULT: usize = 10_000;

fn webhook_memory_key() -> String {
    format!("webhook_msg_{}", Uuid::new_v4())
}

fn whatsapp_memory_key(msg: &crate::channels::traits::ChannelMessage) -> String {
    format!("whatsapp_{}_{}", msg.sender, msg.id)
}

fn hash_webhook_secret(value: &str) -> String {
    use sha2::{Digest, Sha256};

    let digest = Sha256::digest(value.as_bytes());
    hex::encode(digest)
}

/// How often the rate limiter sweeps stale IP entries from its map.
const RATE_LIMITER_SWEEP_INTERVAL_SECS: u64 = 300; // 5 minutes

#[derive(Debug)]
struct SlidingWindowRateLimiter {
    limit_per_window: u32,
    window: Duration,
    max_keys: usize,
    requests: Mutex<(HashMap<String, Vec<Instant>>, Instant)>,
}

impl SlidingWindowRateLimiter {
    fn new(limit_per_window: u32, window: Duration, max_keys: usize) -> Self {
        Self {
            limit_per_window,
            window,
            max_keys: max_keys.max(1),
            requests: Mutex::new((HashMap::new(), Instant::now())),
        }
    }

    fn prune_stale(requests: &mut HashMap<String, Vec<Instant>>, cutoff: Instant) {
        requests.retain(|_, timestamps| {
            timestamps.retain(|t| *t > cutoff);
            !timestamps.is_empty()
        });
    }

    fn allow(&self, key: &str) -> bool {
        if self.limit_per_window == 0 {
            return true;
        }

        let now = Instant::now();
        let cutoff = now.checked_sub(self.window).unwrap_or_else(Instant::now);

        let mut guard = self.requests.lock();
        let (requests, last_sweep) = &mut *guard;

        // Periodic sweep: remove keys with no recent requests
        if last_sweep.elapsed() >= Duration::from_secs(RATE_LIMITER_SWEEP_INTERVAL_SECS) {
            Self::prune_stale(requests, cutoff);
            *last_sweep = now;
        }

        if !requests.contains_key(key) && requests.len() >= self.max_keys {
            // Opportunistic stale cleanup before eviction under cardinality pressure.
            Self::prune_stale(requests, cutoff);
            *last_sweep = now;

            if requests.len() >= self.max_keys {
                let evict_key = requests
                    .iter()
                    .min_by_key(|(_, timestamps)| timestamps.last().copied().unwrap_or(cutoff))
                    .map(|(k, _)| k.clone());
                if let Some(evict_key) = evict_key {
                    requests.remove(&evict_key);
                }
            }
        }

        let entry = requests.entry(key.to_owned()).or_default();
        entry.retain(|instant| *instant > cutoff);

        if entry.len() >= self.limit_per_window as usize {
            return false;
        }

        entry.push(now);
        true
    }
}

#[derive(Debug)]
pub struct GatewayRateLimiter {
    pair: SlidingWindowRateLimiter,
    webhook: SlidingWindowRateLimiter,
}

impl GatewayRateLimiter {
    fn new(pair_per_minute: u32, webhook_per_minute: u32, max_keys: usize) -> Self {
        let window = Duration::from_secs(RATE_LIMIT_WINDOW_SECS);
        Self {
            pair: SlidingWindowRateLimiter::new(pair_per_minute, window, max_keys),
            webhook: SlidingWindowRateLimiter::new(webhook_per_minute, window, max_keys),
        }
    }

    fn allow_pair(&self, key: &str) -> bool {
        self.pair.allow(key)
    }

    fn allow_webhook(&self, key: &str) -> bool {
        self.webhook.allow(key)
    }
}

#[derive(Debug)]
pub struct IdempotencyStore {
    ttl: Duration,
    max_keys: usize,
    keys: Mutex<HashMap<String, Instant>>,
}

impl IdempotencyStore {
    fn new(ttl: Duration, max_keys: usize) -> Self {
        Self {
            ttl,
            max_keys: max_keys.max(1),
            keys: Mutex::new(HashMap::new()),
        }
    }

    /// Returns true if this key is new and is now recorded.
    fn record_if_new(&self, key: &str) -> bool {
        let now = Instant::now();
        let mut keys = self.keys.lock();

        keys.retain(|_, seen_at| now.duration_since(*seen_at) < self.ttl);

        if keys.contains_key(key) {
            return false;
        }

        if keys.len() >= self.max_keys {
            let evict_key = keys
                .iter()
                .min_by_key(|(_, seen_at)| *seen_at)
                .map(|(k, _)| k.clone());
            if let Some(evict_key) = evict_key {
                keys.remove(&evict_key);
            }
        }

        keys.insert(key.to_owned(), now);
        true
    }
}

fn parse_client_ip(value: &str) -> Option<IpAddr> {
    let value = value.trim().trim_matches('"').trim();
    if value.is_empty() {
        return None;
    }

    if let Ok(ip) = value.parse::<IpAddr>() {
        return Some(ip);
    }

    if let Ok(addr) = value.parse::<SocketAddr>() {
        return Some(addr.ip());
    }

    let value = value.trim_matches(['[', ']']);
    value.parse::<IpAddr>().ok()
}

fn forwarded_client_ip(headers: &HeaderMap) -> Option<IpAddr> {
    if let Some(xff) = headers.get("X-Forwarded-For").and_then(|v| v.to_str().ok()) {
        for candidate in xff.split(',') {
            if let Some(ip) = parse_client_ip(candidate) {
                return Some(ip);
            }
        }
    }

    headers
        .get("X-Real-IP")
        .and_then(|v| v.to_str().ok())
        .and_then(parse_client_ip)
}

fn client_key_from_request(
    peer_addr: Option<SocketAddr>,
    headers: &HeaderMap,
    trust_forwarded_headers: bool,
) -> String {
    if trust_forwarded_headers {
        if let Some(ip) = forwarded_client_ip(headers) {
            return ip.to_string();
        }
    }

    peer_addr
        .map(|addr| addr.ip().to_string())
        .unwrap_or_else(|| "unknown".to_string())
}

fn normalize_max_keys(configured: usize, fallback: usize) -> usize {
    if configured == 0 {
        fallback.max(1)
    } else {
        configured
    }
}

/// Shared state for all axum handlers
#[derive(Clone)]
pub struct AppState {
    pub config: Arc<Mutex<Config>>,
    pub provider: Arc<dyn Provider>,
    pub model: String,
    pub temperature: f64,
    pub mem: Arc<dyn Memory>,
    pub auto_save: bool,
    /// SHA-256 hash of `X-Webhook-Secret` (hex-encoded), never plaintext.
    pub webhook_secret_hash: Option<Arc<str>>,
    pub pairing: Arc<PairingGuard>,
    pub trust_forwarded_headers: bool,
    pub rate_limiter: Arc<GatewayRateLimiter>,
    pub idempotency_store: Arc<IdempotencyStore>,
    pub whatsapp: Option<Arc<WhatsAppChannel>>,
    /// `WhatsApp` app secret for webhook signature verification (`X-Hub-Signature-256`)
    pub whatsapp_app_secret: Option<Arc<str>>,
    /// Observability backend for metrics scraping
    pub observer: Arc<dyn crate::observability::Observer>,
}

/// Run the HTTP gateway using axum with proper HTTP/1.1 compliance.
#[allow(clippy::too_many_lines)]
pub async fn run_gateway(host: &str, port: u16, config: Config) -> Result<()> {
    // ── Security: refuse public bind without tunnel or explicit opt-in ──
    if is_public_bind(host) && config.tunnel.provider == "none" && !config.gateway.allow_public_bind
    {
        anyhow::bail!(
            "🛑 Refusing to bind to {host} — gateway would be exposed to the internet.\n\
             Fix: use --host 127.0.0.1 (default), configure a tunnel, or set\n\
             [gateway] allow_public_bind = true in config.toml (NOT recommended)."
        );
    }
    let config_state = Arc::new(Mutex::new(config.clone()));

    let addr: SocketAddr = format!("{host}:{port}").parse()?;
    let listener = tokio::net::TcpListener::bind(addr).await?;
    let actual_port = listener.local_addr()?.port();
    let display_addr = format!("{host}:{actual_port}");

    let provider: Arc<dyn Provider> = Arc::from(providers::create_resilient_provider_with_options(
        config.default_provider.as_deref().unwrap_or("openrouter"),
        config.api_key.as_deref(),
        config.api_url.as_deref(),
        &config.reliability,
        &providers::ProviderRuntimeOptions {
            auth_profile_override: None,
            zeroclaw_dir: config.config_path.parent().map(std::path::PathBuf::from),
            secrets_encrypt: config.secrets.encrypt,
        },
    )?);
    let model = config
        .default_model
        .clone()
        .unwrap_or_else(|| "anthropic/claude-sonnet-4".into());
    let temperature = config.default_temperature;
    let mem: Arc<dyn Memory> = Arc::from(memory::create_memory_with_storage(
        &config.memory,
        Some(&config.storage.provider.config),
        &config.workspace_dir,
        config.api_key.as_deref(),
    )?);
    let runtime: Arc<dyn runtime::RuntimeAdapter> =
        Arc::from(runtime::create_runtime(&config.runtime)?);
    let security = Arc::new(SecurityPolicy::from_config(
        &config.autonomy,
        &config.workspace_dir,
    ));

    let (composio_key, composio_entity_id) = if config.composio.enabled {
        (
            config.composio.api_key.as_deref(),
            Some(config.composio.entity_id.as_str()),
        )
    } else {
        (None, None)
    };

    let _tools_registry = Arc::new(tools::all_tools_with_runtime(
        Arc::new(config.clone()),
        &security,
        runtime,
        Arc::clone(&mem),
        composio_key,
        composio_entity_id,
        &config.browser,
        &config.http_request,
        &config.workspace_dir,
        &config.agents,
        config.api_key.as_deref(),
        &config,
    ));
    // Extract webhook secret for authentication
    let webhook_secret_hash: Option<Arc<str>> =
        config.channels_config.webhook.as_ref().and_then(|webhook| {
            webhook.secret.as_ref().and_then(|raw_secret| {
                let trimmed_secret = raw_secret.trim();
                (!trimmed_secret.is_empty())
                    .then(|| Arc::<str>::from(hash_webhook_secret(trimmed_secret)))
            })
        });

    // WhatsApp channel (if configured)
    let whatsapp_channel: Option<Arc<WhatsAppChannel>> =
        config.channels_config.whatsapp.as_ref().map(|wa| {
            Arc::new(WhatsAppChannel::new(
                wa.access_token.clone(),
                wa.phone_number_id.clone(),
                wa.verify_token.clone(),
                wa.allowed_numbers.clone(),
            ))
        });

    // WhatsApp app secret for webhook signature verification
    // Priority: environment variable > config file
    let whatsapp_app_secret: Option<Arc<str>> = std::env::var("ZEROCLAW_WHATSAPP_APP_SECRET")
        .ok()
        .and_then(|secret| {
            let secret = secret.trim();
            (!secret.is_empty()).then(|| secret.to_owned())
        })
        .or_else(|| {
            config.channels_config.whatsapp.as_ref().and_then(|wa| {
                wa.app_secret
                    .as_deref()
                    .map(str::trim)
                    .filter(|secret| !secret.is_empty())
                    .map(ToOwned::to_owned)
            })
        })
        .map(Arc::from);

    // ── Pairing guard ──────────────────────────────────────
    let pairing = Arc::new(PairingGuard::new(
        config.gateway.require_pairing,
        &config.gateway.paired_tokens,
    ));
    let rate_limit_max_keys = normalize_max_keys(
        config.gateway.rate_limit_max_keys,
        RATE_LIMIT_MAX_KEYS_DEFAULT,
    );
    let rate_limiter = Arc::new(GatewayRateLimiter::new(
        config.gateway.pair_rate_limit_per_minute,
        config.gateway.webhook_rate_limit_per_minute,
        rate_limit_max_keys,
    ));
    let idempotency_max_keys = normalize_max_keys(
        config.gateway.idempotency_max_keys,
        IDEMPOTENCY_MAX_KEYS_DEFAULT,
    );
    let idempotency_store = Arc::new(IdempotencyStore::new(
        Duration::from_secs(config.gateway.idempotency_ttl_secs.max(1)),
        idempotency_max_keys,
    ));

    // ── Tunnel ────────────────────────────────────────────────
    let tunnel = crate::tunnel::create_tunnel(&config.tunnel)?;
    let mut tunnel_url: Option<String> = None;

    if let Some(ref tun) = tunnel {
        println!("🔗 Starting {} tunnel...", tun.name());
        match tun.start(host, actual_port).await {
            Ok(url) => {
                println!("🌐 Tunnel active: {url}");
                tunnel_url = Some(url);
            }
            Err(e) => {
                println!("⚠️  Tunnel failed to start: {e}");
                println!("   Falling back to local-only mode.");
            }
        }
    }

    println!("🦀 ZeroClaw Gateway listening on http://{display_addr}");
    if let Some(ref url) = tunnel_url {
        println!("  🌐 Public URL: {url}");
    }
    println!("  POST /pair      — pair a new client (X-Pairing-Code header)");
    println!("  POST /webhook   — {{\"message\": \"your prompt\"}}");
    if whatsapp_channel.is_some() {
        println!("  GET  /whatsapp  — Meta webhook verification");
        println!("  POST /whatsapp  — WhatsApp message webhook");
    }
    println!("  GET  /health    — health check");
    println!("  GET  /metrics   — Prometheus metrics");
    if let Some(code) = pairing.pairing_code() {
        println!();
        println!("  🔐 PAIRING REQUIRED — use this one-time code:");
        println!("     ┌──────────────┐");
        println!("     │  {code}  │");
        println!("     └──────────────┘");
        println!("     Send: POST /pair with header X-Pairing-Code: {code}");
    } else if pairing.require_pairing() {
        println!("  🔒 Pairing: ACTIVE (bearer token required)");
    } else {
        println!("  ⚠️  Pairing: DISABLED (all requests accepted)");
    }
    println!("  Press Ctrl+C to stop.\n");

    crate::health::mark_component_ok("gateway");

    // Build shared state
    let observer: Arc<dyn crate::observability::Observer> =
        Arc::from(crate::observability::create_observer(&config.observability));

    let state = AppState {
        config: config_state,
        provider,
        model,
        temperature,
        mem,
        auto_save: config.memory.auto_save,
        webhook_secret_hash,
        pairing,
        trust_forwarded_headers: config.gateway.trust_forwarded_headers,
        rate_limiter,
        idempotency_store,
        whatsapp: whatsapp_channel,
        whatsapp_app_secret,
        observer,
    };

    // Build router with middleware
    let app = Router::new()
        .route("/health", get(handle_health))
        .route("/metrics", get(handle_metrics))
        .route("/pair", post(handle_pair))
        .route("/webhook", post(handle_webhook))
        .route("/whatsapp", get(handle_whatsapp_verify))
        .route("/whatsapp", post(handle_whatsapp_message))
        .with_state(state)
        .layer(RequestBodyLimitLayer::new(MAX_BODY_SIZE))
        .layer(TimeoutLayer::with_status_code(
            StatusCode::REQUEST_TIMEOUT,
            Duration::from_secs(REQUEST_TIMEOUT_SECS),
        ));

    // Run the server
    axum::serve(
        listener,
        app.into_make_service_with_connect_info::<SocketAddr>(),
    )
    .await?;

    Ok(())
}

// ══════════════════════════════════════════════════════════════════════════════
// AXUM HANDLERS
// ══════════════════════════════════════════════════════════════════════════════

/// GET /health — always public (no secrets leaked)
async fn handle_health(State(state): State<AppState>) -> impl IntoResponse {
    let body = serde_json::json!({
        "status": "ok",
        "paired": state.pairing.is_paired(),
        "runtime": crate::health::snapshot_json(),
    });
    Json(body)
}

/// Prometheus content type for text exposition format.
const PROMETHEUS_CONTENT_TYPE: &str = "text/plain; version=0.0.4; charset=utf-8";

/// GET /metrics — Prometheus text exposition format
async fn handle_metrics(State(state): State<AppState>) -> impl IntoResponse {
    let body = if let Some(prom) = state
        .observer
        .as_ref()
        .as_any()
        .downcast_ref::<crate::observability::PrometheusObserver>()
    {
        prom.encode()
    } else {
        String::from("# Prometheus backend not enabled. Set [observability] backend = \"prometheus\" in config.\n")
    };

    (
        StatusCode::OK,
        [(header::CONTENT_TYPE, PROMETHEUS_CONTENT_TYPE)],
        body,
    )
}

/// POST /pair — exchange one-time code for bearer token
async fn handle_pair(
    State(state): State<AppState>,
    ConnectInfo(peer_addr): ConnectInfo<SocketAddr>,
    headers: HeaderMap,
) -> impl IntoResponse {
    let client_key =
        client_key_from_request(Some(peer_addr), &headers, state.trust_forwarded_headers);
    if !state.rate_limiter.allow_pair(&client_key) {
        tracing::warn!("/pair rate limit exceeded for key: {client_key}");
        let err = serde_json::json!({
            "error": "Too many pairing requests. Please retry later.",
            "retry_after": RATE_LIMIT_WINDOW_SECS,
        });
        return (StatusCode::TOO_MANY_REQUESTS, Json(err));
    }

    let code = headers
        .get("X-Pairing-Code")
        .and_then(|v| v.to_str().ok())
        .unwrap_or("");

    match state.pairing.try_pair(code) {
        Ok(Some(token)) => {
            tracing::info!("🔐 New client paired successfully");
            if let Err(err) = persist_pairing_tokens(&state.config, &state.pairing) {
                tracing::error!("🔐 Pairing succeeded but token persistence failed: {err:#}");
                let body = serde_json::json!({
                    "paired": true,
                    "persisted": false,
                    "token": token,
                    "message": "Paired for this process, but failed to persist token to config.toml. Check config path and write permissions.",
                });
                return (StatusCode::OK, Json(body));
            }

            let body = serde_json::json!({
                "paired": true,
                "persisted": true,
                "token": token,
                "message": "Save this token — use it as Authorization: Bearer <token>"
            });
            (StatusCode::OK, Json(body))
        }
        Ok(None) => {
            tracing::warn!("🔐 Pairing attempt with invalid code");
            let err = serde_json::json!({"error": "Invalid pairing code"});
            (StatusCode::FORBIDDEN, Json(err))
        }
        Err(lockout_secs) => {
            tracing::warn!(
                "🔐 Pairing locked out — too many failed attempts ({lockout_secs}s remaining)"
            );
            let err = serde_json::json!({
                "error": format!("Too many failed attempts. Try again in {lockout_secs}s."),
                "retry_after": lockout_secs
            });
            (StatusCode::TOO_MANY_REQUESTS, Json(err))
        }
    }
}

fn persist_pairing_tokens(config: &Arc<Mutex<Config>>, pairing: &PairingGuard) -> Result<()> {
    let paired_tokens = pairing.tokens();
    let mut cfg = config.lock();
    cfg.gateway.paired_tokens = paired_tokens;
    cfg.save()
        .context("Failed to persist paired tokens to config.toml")
}

/// Webhook request body
#[derive(serde::Deserialize)]
pub struct WebhookBody {
    pub message: String,
}

/// POST /webhook — main webhook endpoint
async fn handle_webhook(
    State(state): State<AppState>,
    ConnectInfo(peer_addr): ConnectInfo<SocketAddr>,
    headers: HeaderMap,
    body: Result<Json<WebhookBody>, axum::extract::rejection::JsonRejection>,
) -> impl IntoResponse {
    let client_key =
        client_key_from_request(Some(peer_addr), &headers, state.trust_forwarded_headers);
    if !state.rate_limiter.allow_webhook(&client_key) {
        tracing::warn!("/webhook rate limit exceeded for key: {client_key}");
        let err = serde_json::json!({
            "error": "Too many webhook requests. Please retry later.",
            "retry_after": RATE_LIMIT_WINDOW_SECS,
        });
        return (StatusCode::TOO_MANY_REQUESTS, Json(err));
    }

    // ── Bearer token auth (pairing) ──
    if state.pairing.require_pairing() {
        let auth = headers
            .get(header::AUTHORIZATION)
            .and_then(|v| v.to_str().ok())
            .unwrap_or("");
        let token = auth.strip_prefix("Bearer ").unwrap_or("");
        if !state.pairing.is_authenticated(token) {
            tracing::warn!("Webhook: rejected — not paired / invalid bearer token");
            let err = serde_json::json!({
                "error": "Unauthorized — pair first via POST /pair, then send Authorization: Bearer <token>"
            });
            return (StatusCode::UNAUTHORIZED, Json(err));
        }
    }

    // ── Webhook secret auth (optional, additional layer) ──
    if let Some(ref secret_hash) = state.webhook_secret_hash {
        let header_hash = headers
            .get("X-Webhook-Secret")
            .and_then(|v| v.to_str().ok())
            .map(str::trim)
            .filter(|value| !value.is_empty())
            .map(hash_webhook_secret);
        match header_hash {
            Some(val) if constant_time_eq(&val, secret_hash.as_ref()) => {}
            _ => {
                tracing::warn!("Webhook: rejected request — invalid or missing X-Webhook-Secret");
                let err = serde_json::json!({"error": "Unauthorized — invalid or missing X-Webhook-Secret header"});
                return (StatusCode::UNAUTHORIZED, Json(err));
            }
        }
    }

    // ── Parse body ──
    let Json(webhook_body) = match body {
        Ok(b) => b,
        Err(e) => {
            tracing::warn!("Webhook JSON parse error: {e}");
            let err = serde_json::json!({
                "error": "Invalid JSON body. Expected: {\"message\": \"...\"}"
            });
            return (StatusCode::BAD_REQUEST, Json(err));
        }
    };

    // ── Idempotency (optional) ──
    if let Some(idempotency_key) = headers
        .get("X-Idempotency-Key")
        .and_then(|v| v.to_str().ok())
        .map(str::trim)
        .filter(|value| !value.is_empty())
    {
        if !state.idempotency_store.record_if_new(idempotency_key) {
            tracing::info!("Webhook duplicate ignored (idempotency key: {idempotency_key})");
            let body = serde_json::json!({
                "status": "duplicate",
                "idempotent": true,
                "message": "Request already processed for this idempotency key"
            });
            return (StatusCode::OK, Json(body));
        }
    }

    let message = &webhook_body.message;

    if state.auto_save {
        let key = webhook_memory_key();
        let _ = state
            .mem
            .store(&key, message, MemoryCategory::Conversation, None)
            .await;
    }

    let provider_label = state
        .config
        .lock()
        .default_provider
        .clone()
        .unwrap_or_else(|| "unknown".to_string());
    let model_label = state.model.clone();
    let started_at = Instant::now();

    state
        .observer
        .record_event(&crate::observability::ObserverEvent::AgentStart {
            provider: provider_label.clone(),
            model: model_label.clone(),
        });
    state
        .observer
        .record_event(&crate::observability::ObserverEvent::LlmRequest {
            provider: provider_label.clone(),
            model: model_label.clone(),
            messages_count: 1,
        });

    match state
        .provider
        .simple_chat(message, &state.model, state.temperature)
        .await
    {
        Ok(response) => {
            let duration = started_at.elapsed();
            state
                .observer
                .record_event(&crate::observability::ObserverEvent::LlmResponse {
                    provider: provider_label.clone(),
                    model: model_label.clone(),
                    duration,
                    success: true,
                    error_message: None,
                });
            state.observer.record_metric(
                &crate::observability::traits::ObserverMetric::RequestLatency(duration),
            );
            state
                .observer
                .record_event(&crate::observability::ObserverEvent::AgentEnd {
                    provider: provider_label,
                    model: model_label,
                    duration,
                    tokens_used: None,
                    cost_usd: None,
                });

            let body = serde_json::json!({"response": response, "model": state.model});
            (StatusCode::OK, Json(body))
        }
        Err(e) => {
            let duration = started_at.elapsed();
            let sanitized = providers::sanitize_api_error(&e.to_string());

            state
                .observer
                .record_event(&crate::observability::ObserverEvent::LlmResponse {
                    provider: provider_label.clone(),
                    model: model_label.clone(),
                    duration,
                    success: false,
                    error_message: Some(sanitized.clone()),
                });
            state.observer.record_metric(
                &crate::observability::traits::ObserverMetric::RequestLatency(duration),
            );
            state
                .observer
                .record_event(&crate::observability::ObserverEvent::Error {
                    component: "gateway".to_string(),
                    message: sanitized.clone(),
                });
            state
                .observer
                .record_event(&crate::observability::ObserverEvent::AgentEnd {
                    provider: provider_label,
                    model: model_label,
                    duration,
                    tokens_used: None,
                    cost_usd: None,
                });

            tracing::error!("Webhook provider error: {}", sanitized);
            let err = serde_json::json!({"error": "LLM request failed"});
            (StatusCode::INTERNAL_SERVER_ERROR, Json(err))
        }
    }
}

/// `WhatsApp` verification query params
#[derive(serde::Deserialize)]
pub struct WhatsAppVerifyQuery {
    #[serde(rename = "hub.mode")]
    pub mode: Option<String>,
    #[serde(rename = "hub.verify_token")]
    pub verify_token: Option<String>,
    #[serde(rename = "hub.challenge")]
    pub challenge: Option<String>,
}

/// GET /whatsapp — Meta webhook verification
async fn handle_whatsapp_verify(
    State(state): State<AppState>,
    Query(params): Query<WhatsAppVerifyQuery>,
) -> impl IntoResponse {
    let Some(ref wa) = state.whatsapp else {
        return (StatusCode::NOT_FOUND, "WhatsApp not configured".to_string());
    };

    // Verify the token matches (constant-time comparison to prevent timing attacks)
    let token_matches = params
        .verify_token
        .as_deref()
        .is_some_and(|t| constant_time_eq(t, wa.verify_token()));
    if params.mode.as_deref() == Some("subscribe") && token_matches {
        if let Some(ch) = params.challenge {
            tracing::info!("WhatsApp webhook verified successfully");
            return (StatusCode::OK, ch);
        }
        return (StatusCode::BAD_REQUEST, "Missing hub.challenge".to_string());
    }

    tracing::warn!("WhatsApp webhook verification failed — token mismatch");
    (StatusCode::FORBIDDEN, "Forbidden".to_string())
}

/// Verify `WhatsApp` webhook signature (`X-Hub-Signature-256`).
/// Returns true if the signature is valid, false otherwise.
/// See: <https://developers.facebook.com/docs/graph-api/webhooks/getting-started#verification-requests>
pub fn verify_whatsapp_signature(app_secret: &str, body: &[u8], signature_header: &str) -> bool {
    use hmac::{Hmac, Mac};
    use sha2::Sha256;

    // Signature format: "sha256=<hex_signature>"
    let Some(hex_sig) = signature_header.strip_prefix("sha256=") else {
        return false;
    };

    // Decode hex signature
    let Ok(expected) = hex::decode(hex_sig) else {
        return false;
    };

    // Compute HMAC-SHA256
    let Ok(mut mac) = Hmac::<Sha256>::new_from_slice(app_secret.as_bytes()) else {
        return false;
    };
    mac.update(body);

    // Constant-time comparison
    mac.verify_slice(&expected).is_ok()
}

/// POST /whatsapp — incoming message webhook
async fn handle_whatsapp_message(
    State(state): State<AppState>,
    headers: HeaderMap,
    body: Bytes,
) -> impl IntoResponse {
    let Some(ref wa) = state.whatsapp else {
        return (
            StatusCode::NOT_FOUND,
            Json(serde_json::json!({"error": "WhatsApp not configured"})),
        );
    };

    // ── Security: Verify X-Hub-Signature-256 if app_secret is configured ──
    if let Some(ref app_secret) = state.whatsapp_app_secret {
        let signature = headers
            .get("X-Hub-Signature-256")
            .and_then(|v| v.to_str().ok())
            .unwrap_or("");

        if !verify_whatsapp_signature(app_secret, &body, signature) {
            tracing::warn!(
                "WhatsApp webhook signature verification failed (signature: {})",
                if signature.is_empty() {
                    "missing"
                } else {
                    "invalid"
                }
            );
            return (
                StatusCode::UNAUTHORIZED,
                Json(serde_json::json!({"error": "Invalid signature"})),
            );
        }
    }

    // Parse JSON body
    let Ok(payload) = serde_json::from_slice::<serde_json::Value>(&body) else {
        return (
            StatusCode::BAD_REQUEST,
            Json(serde_json::json!({"error": "Invalid JSON payload"})),
        );
    };

    // Parse messages from the webhook payload
    let messages = wa.parse_webhook_payload(&payload);

    if messages.is_empty() {
        // Acknowledge the webhook even if no messages (could be status updates)
        return (StatusCode::OK, Json(serde_json::json!({"status": "ok"})));
    }

    // Process each message
    for msg in &messages {
        tracing::info!(
            "WhatsApp message from {}: {}",
            msg.sender,
            truncate_with_ellipsis(&msg.content, 50)
        );

        // Auto-save to memory
        if state.auto_save {
            let key = whatsapp_memory_key(msg);
            let _ = state
                .mem
                .store(&key, &msg.content, MemoryCategory::Conversation, None)
                .await;
        }

        // Call the LLM
        match state
            .provider
            .simple_chat(&msg.content, &state.model, state.temperature)
            .await
        {
            Ok(response) => {
                // Send reply via WhatsApp
                if let Err(e) = wa
                    .send(&SendMessage::new(response, &msg.reply_target))
                    .await
                {
                    tracing::error!("Failed to send WhatsApp reply: {e}");
                }
            }
            Err(e) => {
                tracing::error!("LLM error for WhatsApp message: {e:#}");
                let _ = wa
                    .send(&SendMessage::new(
                        "Sorry, I couldn't process your message right now.",
                        &msg.reply_target,
                    ))
                    .await;
            }
        }
    }

    // Acknowledge the webhook
    (StatusCode::OK, Json(serde_json::json!({"status": "ok"})))
}

#[cfg(test)]
mod tests {
    use super::*;
    use crate::channels::traits::ChannelMessage;
    use crate::memory::{Memory, MemoryCategory, MemoryEntry};
    use crate::providers::Provider;
    use async_trait::async_trait;
    use axum::http::HeaderValue;
    use axum::response::IntoResponse;
    use http_body_util::BodyExt;
    use parking_lot::Mutex;
    use std::sync::atomic::{AtomicUsize, Ordering};

    #[test]
    fn security_body_limit_is_64kb() {
        assert_eq!(MAX_BODY_SIZE, 65_536);
    }

    #[test]
    fn security_timeout_is_30_seconds() {
        assert_eq!(REQUEST_TIMEOUT_SECS, 30);
    }

    #[test]
    fn webhook_body_requires_message_field() {
        let valid = r#"{"message": "hello"}"#;
        let parsed: Result<WebhookBody, _> = serde_json::from_str(valid);
        assert!(parsed.is_ok());
        assert_eq!(parsed.unwrap().message, "hello");

        let missing = r#"{"other": "field"}"#;
        let parsed: Result<WebhookBody, _> = serde_json::from_str(missing);
        assert!(parsed.is_err());
    }

    #[test]
    fn whatsapp_query_fields_are_optional() {
        let q = WhatsAppVerifyQuery {
            mode: None,
            verify_token: None,
            challenge: None,
        };
        assert!(q.mode.is_none());
    }

    #[test]
    fn app_state_is_clone() {
        fn assert_clone<T: Clone>() {}
        assert_clone::<AppState>();
    }

    #[tokio::test]
    async fn metrics_endpoint_returns_hint_when_prometheus_is_disabled() {
        let state = AppState {
            config: Arc::new(Mutex::new(Config::default())),
            provider: Arc::new(MockProvider::default()),
            model: "test-model".into(),
            temperature: 0.0,
            mem: Arc::new(MockMemory),
            auto_save: false,
            webhook_secret_hash: None,
            pairing: Arc::new(PairingGuard::new(false, &[])),
            trust_forwarded_headers: false,
            rate_limiter: Arc::new(GatewayRateLimiter::new(100, 100, 100)),
            idempotency_store: Arc::new(IdempotencyStore::new(Duration::from_secs(300), 1000)),
            whatsapp: None,
            whatsapp_app_secret: None,
            observer: Arc::new(crate::observability::NoopObserver),
        };

        let response = handle_metrics(State(state)).await.into_response();
        assert_eq!(response.status(), StatusCode::OK);
        assert_eq!(
            response
                .headers()
                .get(header::CONTENT_TYPE)
                .and_then(|value| value.to_str().ok()),
            Some(PROMETHEUS_CONTENT_TYPE)
        );

        let body = response.into_body().collect().await.unwrap().to_bytes();
        let text = String::from_utf8(body.to_vec()).unwrap();
        assert!(text.contains("Prometheus backend not enabled"));
    }

    #[tokio::test]
    async fn metrics_endpoint_renders_prometheus_output() {
        let prom = Arc::new(crate::observability::PrometheusObserver::new());
        crate::observability::Observer::record_event(
            prom.as_ref(),
            &crate::observability::ObserverEvent::HeartbeatTick,
        );

        let observer: Arc<dyn crate::observability::Observer> = prom;
        let state = AppState {
            config: Arc::new(Mutex::new(Config::default())),
            provider: Arc::new(MockProvider::default()),
            model: "test-model".into(),
            temperature: 0.0,
            mem: Arc::new(MockMemory),
            auto_save: false,
            webhook_secret_hash: None,
            pairing: Arc::new(PairingGuard::new(false, &[])),
            trust_forwarded_headers: false,
            rate_limiter: Arc::new(GatewayRateLimiter::new(100, 100, 100)),
            idempotency_store: Arc::new(IdempotencyStore::new(Duration::from_secs(300), 1000)),
            whatsapp: None,
            whatsapp_app_secret: None,
            observer,
        };

        let response = handle_metrics(State(state)).await.into_response();
        assert_eq!(response.status(), StatusCode::OK);

        let body = response.into_body().collect().await.unwrap().to_bytes();
        let text = String::from_utf8(body.to_vec()).unwrap();
        assert!(text.contains("zeroclaw_heartbeat_ticks_total 1"));
    }

    #[test]
    fn gateway_rate_limiter_blocks_after_limit() {
        let limiter = GatewayRateLimiter::new(2, 2, 100);
        assert!(limiter.allow_pair("127.0.0.1"));
        assert!(limiter.allow_pair("127.0.0.1"));
        assert!(!limiter.allow_pair("127.0.0.1"));
    }

    #[test]
    fn rate_limiter_sweep_removes_stale_entries() {
        let limiter = SlidingWindowRateLimiter::new(10, Duration::from_secs(60), 100);
        // Add entries for multiple IPs
        assert!(limiter.allow("ip-1"));
        assert!(limiter.allow("ip-2"));
        assert!(limiter.allow("ip-3"));

        {
            let guard = limiter.requests.lock();
            assert_eq!(guard.0.len(), 3);
        }

        // Force a sweep by backdating last_sweep
        {
            let mut guard = limiter.requests.lock();
            guard.1 = Instant::now()
                .checked_sub(Duration::from_secs(RATE_LIMITER_SWEEP_INTERVAL_SECS + 1))
                .unwrap();
            // Clear timestamps for ip-2 and ip-3 to simulate stale entries
            guard.0.get_mut("ip-2").unwrap().clear();
            guard.0.get_mut("ip-3").unwrap().clear();
        }

        // Next allow() call should trigger sweep and remove stale entries
        assert!(limiter.allow("ip-1"));

        {
            let guard = limiter.requests.lock();
            assert_eq!(guard.0.len(), 1, "Stale entries should have been swept");
            assert!(guard.0.contains_key("ip-1"));
        }
    }

    #[test]
    fn rate_limiter_zero_limit_always_allows() {
        let limiter = SlidingWindowRateLimiter::new(0, Duration::from_secs(60), 10);
        for _ in 0..100 {
            assert!(limiter.allow("any-key"));
        }
    }

    #[test]
    fn idempotency_store_rejects_duplicate_key() {
        let store = IdempotencyStore::new(Duration::from_secs(30), 10);
        assert!(store.record_if_new("req-1"));
        assert!(!store.record_if_new("req-1"));
        assert!(store.record_if_new("req-2"));
    }

    #[test]
    fn rate_limiter_bounded_cardinality_evicts_oldest_key() {
        let limiter = SlidingWindowRateLimiter::new(5, Duration::from_secs(60), 2);
        assert!(limiter.allow("ip-1"));
        assert!(limiter.allow("ip-2"));
        assert!(limiter.allow("ip-3"));

        let guard = limiter.requests.lock();
        assert_eq!(guard.0.len(), 2);
        assert!(guard.0.contains_key("ip-2"));
        assert!(guard.0.contains_key("ip-3"));
    }

    #[test]
    fn idempotency_store_bounded_cardinality_evicts_oldest_key() {
        let store = IdempotencyStore::new(Duration::from_secs(300), 2);
        assert!(store.record_if_new("k1"));
        std::thread::sleep(Duration::from_millis(2));
        assert!(store.record_if_new("k2"));
        std::thread::sleep(Duration::from_millis(2));
        assert!(store.record_if_new("k3"));

        let keys = store.keys.lock();
        assert_eq!(keys.len(), 2);
        assert!(!keys.contains_key("k1"));
        assert!(keys.contains_key("k2"));
        assert!(keys.contains_key("k3"));
    }

    #[test]
    fn client_key_defaults_to_peer_addr_when_untrusted_proxy_mode() {
        let peer = SocketAddr::from(([10, 0, 0, 5], 3000));
        let mut headers = HeaderMap::new();
        headers.insert(
            "X-Forwarded-For",
            HeaderValue::from_static("198.51.100.10, 203.0.113.11"),
        );

        let key = client_key_from_request(Some(peer), &headers, false);
        assert_eq!(key, "10.0.0.5");
    }

    #[test]
    fn client_key_uses_forwarded_ip_only_in_trusted_proxy_mode() {
        let peer = SocketAddr::from(([10, 0, 0, 5], 3000));
        let mut headers = HeaderMap::new();
        headers.insert(
            "X-Forwarded-For",
            HeaderValue::from_static("198.51.100.10, 203.0.113.11"),
        );

        let key = client_key_from_request(Some(peer), &headers, true);
        assert_eq!(key, "198.51.100.10");
    }

    #[test]
    fn client_key_falls_back_to_peer_when_forwarded_header_invalid() {
        let peer = SocketAddr::from(([10, 0, 0, 5], 3000));
        let mut headers = HeaderMap::new();
        headers.insert("X-Forwarded-For", HeaderValue::from_static("garbage-value"));

        let key = client_key_from_request(Some(peer), &headers, true);
        assert_eq!(key, "10.0.0.5");
    }

    #[test]
    fn normalize_max_keys_uses_fallback_for_zero() {
        assert_eq!(normalize_max_keys(0, 10_000), 10_000);
        assert_eq!(normalize_max_keys(0, 0), 1);
    }

    #[test]
    fn normalize_max_keys_preserves_nonzero_values() {
        assert_eq!(normalize_max_keys(2_048, 10_000), 2_048);
        assert_eq!(normalize_max_keys(1, 10_000), 1);
    }

    #[test]
    fn persist_pairing_tokens_writes_config_tokens() {
        let temp = tempfile::tempdir().unwrap();
        let config_path = temp.path().join("config.toml");
        let workspace_path = temp.path().join("workspace");

        let mut config = Config::default();
        config.config_path = config_path.clone();
        config.workspace_dir = workspace_path;
        config.save().unwrap();

        let guard = PairingGuard::new(true, &[]);
        let code = guard.pairing_code().unwrap();
        let token = guard.try_pair(&code).unwrap().unwrap();
        assert!(guard.is_authenticated(&token));

        let shared_config = Arc::new(Mutex::new(config));
        persist_pairing_tokens(&shared_config, &guard).unwrap();

        let saved = std::fs::read_to_string(config_path).unwrap();
        let parsed: Config = toml::from_str(&saved).unwrap();
        assert_eq!(parsed.gateway.paired_tokens.len(), 1);
        let persisted = &parsed.gateway.paired_tokens[0];
        assert_eq!(persisted.len(), 64);
        assert!(persisted.chars().all(|c| c.is_ascii_hexdigit()));
    }

    #[test]
    fn webhook_memory_key_is_unique() {
        let key1 = webhook_memory_key();
        let key2 = webhook_memory_key();

        assert!(key1.starts_with("webhook_msg_"));
        assert!(key2.starts_with("webhook_msg_"));
        assert_ne!(key1, key2);
    }

    #[test]
    fn whatsapp_memory_key_includes_sender_and_message_id() {
        let msg = ChannelMessage {
            id: "wamid-123".into(),
            sender: "+1234567890".into(),
            reply_target: "+1234567890".into(),
            content: "hello".into(),
            channel: "whatsapp".into(),
            timestamp: 1,
        };

        let key = whatsapp_memory_key(&msg);
        assert_eq!(key, "whatsapp_+1234567890_wamid-123");
    }

    #[derive(Default)]
    struct MockMemory;

    #[async_trait]
    impl Memory for MockMemory {
        fn name(&self) -> &str {
            "mock"
        }

        async fn store(
            &self,
            _key: &str,
            _content: &str,
            _category: MemoryCategory,
            _session_id: Option<&str>,
        ) -> anyhow::Result<()> {
            Ok(())
        }

        async fn recall(
            &self,
            _query: &str,
            _limit: usize,
            _session_id: Option<&str>,
        ) -> anyhow::Result<Vec<MemoryEntry>> {
            Ok(Vec::new())
        }

        async fn get(&self, _key: &str) -> anyhow::Result<Option<MemoryEntry>> {
            Ok(None)
        }

        async fn list(
            &self,
            _category: Option<&MemoryCategory>,
            _session_id: Option<&str>,
        ) -> anyhow::Result<Vec<MemoryEntry>> {
            Ok(Vec::new())
        }

        async fn forget(&self, _key: &str) -> anyhow::Result<bool> {
            Ok(false)
        }

        async fn count(&self) -> anyhow::Result<usize> {
            Ok(0)
        }

        async fn health_check(&self) -> bool {
            true
        }
    }

    #[derive(Default)]
    struct MockProvider {
        calls: AtomicUsize,
    }

    #[async_trait]
    impl Provider for MockProvider {
        async fn chat_with_system(
            &self,
            _system_prompt: Option<&str>,
            _message: &str,
            _model: &str,
            _temperature: f64,
        ) -> anyhow::Result<String> {
            self.calls.fetch_add(1, Ordering::SeqCst);
            Ok("ok".into())
        }
    }

    #[derive(Default)]
    struct TrackingMemory {
        keys: Mutex<Vec<String>>,
    }

    #[async_trait]
    impl Memory for TrackingMemory {
        fn name(&self) -> &str {
            "tracking"
        }

        async fn store(
            &self,
            key: &str,
            _content: &str,
            _category: MemoryCategory,
            _session_id: Option<&str>,
        ) -> anyhow::Result<()> {
            self.keys.lock().push(key.to_string());
            Ok(())
        }

        async fn recall(
            &self,
            _query: &str,
            _limit: usize,
            _session_id: Option<&str>,
        ) -> anyhow::Result<Vec<MemoryEntry>> {
            Ok(Vec::new())
        }

        async fn get(&self, _key: &str) -> anyhow::Result<Option<MemoryEntry>> {
            Ok(None)
        }

        async fn list(
            &self,
            _category: Option<&MemoryCategory>,
            _session_id: Option<&str>,
        ) -> anyhow::Result<Vec<MemoryEntry>> {
            Ok(Vec::new())
        }

        async fn forget(&self, _key: &str) -> anyhow::Result<bool> {
            Ok(false)
        }

        async fn count(&self) -> anyhow::Result<usize> {
            let size = self.keys.lock().len();
            Ok(size)
        }

        async fn health_check(&self) -> bool {
            true
        }
    }

    fn test_connect_info() -> ConnectInfo<SocketAddr> {
        ConnectInfo(SocketAddr::from(([127, 0, 0, 1], 30_300)))
    }

    #[tokio::test]
    async fn webhook_idempotency_skips_duplicate_provider_calls() {
        let provider_impl = Arc::new(MockProvider::default());
        let provider: Arc<dyn Provider> = provider_impl.clone();
        let memory: Arc<dyn Memory> = Arc::new(MockMemory);

        let state = AppState {
            config: Arc::new(Mutex::new(Config::default())),
            provider,
            model: "test-model".into(),
            temperature: 0.0,
            mem: memory,
            auto_save: false,
            webhook_secret_hash: None,
            pairing: Arc::new(PairingGuard::new(false, &[])),
            trust_forwarded_headers: false,
            rate_limiter: Arc::new(GatewayRateLimiter::new(100, 100, 100)),
            idempotency_store: Arc::new(IdempotencyStore::new(Duration::from_secs(300), 1000)),
            whatsapp: None,
            whatsapp_app_secret: None,
            observer: Arc::new(crate::observability::NoopObserver),
        };

        let mut headers = HeaderMap::new();
        headers.insert("X-Idempotency-Key", HeaderValue::from_static("abc-123"));

        let body = Ok(Json(WebhookBody {
            message: "hello".into(),
        }));
        let first = handle_webhook(
            State(state.clone()),
            test_connect_info(),
            headers.clone(),
            body,
        )
        .await
        .into_response();
        assert_eq!(first.status(), StatusCode::OK);

        let body = Ok(Json(WebhookBody {
            message: "hello".into(),
        }));
        let second = handle_webhook(State(state), test_connect_info(), headers, body)
            .await
            .into_response();
        assert_eq!(second.status(), StatusCode::OK);

        let payload = second.into_body().collect().await.unwrap().to_bytes();
        let parsed: serde_json::Value = serde_json::from_slice(&payload).unwrap();
        assert_eq!(parsed["status"], "duplicate");
        assert_eq!(parsed["idempotent"], true);
        assert_eq!(provider_impl.calls.load(Ordering::SeqCst), 1);
    }

    #[tokio::test]
    async fn webhook_autosave_stores_distinct_keys_per_request() {
        let provider_impl = Arc::new(MockProvider::default());
        let provider: Arc<dyn Provider> = provider_impl.clone();

        let tracking_impl = Arc::new(TrackingMemory::default());
        let memory: Arc<dyn Memory> = tracking_impl.clone();

        let state = AppState {
            config: Arc::new(Mutex::new(Config::default())),
            provider,
            model: "test-model".into(),
            temperature: 0.0,
            mem: memory,
            auto_save: true,
            webhook_secret_hash: None,
            pairing: Arc::new(PairingGuard::new(false, &[])),
            trust_forwarded_headers: false,
            rate_limiter: Arc::new(GatewayRateLimiter::new(100, 100, 100)),
            idempotency_store: Arc::new(IdempotencyStore::new(Duration::from_secs(300), 1000)),
            whatsapp: None,
            whatsapp_app_secret: None,
            observer: Arc::new(crate::observability::NoopObserver),
        };

        let headers = HeaderMap::new();

        let body1 = Ok(Json(WebhookBody {
            message: "hello one".into(),
        }));
        let first = handle_webhook(
            State(state.clone()),
            test_connect_info(),
            headers.clone(),
            body1,
        )
        .await
        .into_response();
        assert_eq!(first.status(), StatusCode::OK);

        let body2 = Ok(Json(WebhookBody {
            message: "hello two".into(),
        }));
        let second = handle_webhook(State(state), test_connect_info(), headers, body2)
            .await
            .into_response();
        assert_eq!(second.status(), StatusCode::OK);

        let keys = tracking_impl.keys.lock().clone();
        assert_eq!(keys.len(), 2);
        assert_ne!(keys[0], keys[1]);
        assert!(keys[0].starts_with("webhook_msg_"));
        assert!(keys[1].starts_with("webhook_msg_"));
        assert_eq!(provider_impl.calls.load(Ordering::SeqCst), 2);
    }

    #[test]
    fn webhook_secret_hash_is_deterministic_and_nonempty() {
        let one = hash_webhook_secret("secret-value");
        let two = hash_webhook_secret("secret-value");
        let other = hash_webhook_secret("other-value");

        assert_eq!(one, two);
        assert_ne!(one, other);
        assert_eq!(one.len(), 64);
    }

    #[tokio::test]
    async fn webhook_secret_hash_rejects_missing_header() {
        let provider_impl = Arc::new(MockProvider::default());
        let provider: Arc<dyn Provider> = provider_impl.clone();
        let memory: Arc<dyn Memory> = Arc::new(MockMemory);

        let state = AppState {
            config: Arc::new(Mutex::new(Config::default())),
            provider,
            model: "test-model".into(),
            temperature: 0.0,
            mem: memory,
            auto_save: false,
            webhook_secret_hash: Some(Arc::from(hash_webhook_secret("super-secret"))),
            pairing: Arc::new(PairingGuard::new(false, &[])),
            trust_forwarded_headers: false,
            rate_limiter: Arc::new(GatewayRateLimiter::new(100, 100, 100)),
            idempotency_store: Arc::new(IdempotencyStore::new(Duration::from_secs(300), 1000)),
            whatsapp: None,
            whatsapp_app_secret: None,
            observer: Arc::new(crate::observability::NoopObserver),
        };

        let response = handle_webhook(
            State(state),
            test_connect_info(),
            HeaderMap::new(),
            Ok(Json(WebhookBody {
                message: "hello".into(),
            })),
        )
        .await
        .into_response();

        assert_eq!(response.status(), StatusCode::UNAUTHORIZED);
        assert_eq!(provider_impl.calls.load(Ordering::SeqCst), 0);
    }

    #[tokio::test]
    async fn webhook_secret_hash_rejects_invalid_header() {
        let provider_impl = Arc::new(MockProvider::default());
        let provider: Arc<dyn Provider> = provider_impl.clone();
        let memory: Arc<dyn Memory> = Arc::new(MockMemory);

        let state = AppState {
            config: Arc::new(Mutex::new(Config::default())),
            provider,
            model: "test-model".into(),
            temperature: 0.0,
            mem: memory,
            auto_save: false,
            webhook_secret_hash: Some(Arc::from(hash_webhook_secret("super-secret"))),
            pairing: Arc::new(PairingGuard::new(false, &[])),
            trust_forwarded_headers: false,
            rate_limiter: Arc::new(GatewayRateLimiter::new(100, 100, 100)),
            idempotency_store: Arc::new(IdempotencyStore::new(Duration::from_secs(300), 1000)),
            whatsapp: None,
            whatsapp_app_secret: None,
            observer: Arc::new(crate::observability::NoopObserver),
        };

        let mut headers = HeaderMap::new();
        headers.insert("X-Webhook-Secret", HeaderValue::from_static("wrong-secret"));

        let response = handle_webhook(
            State(state),
            test_connect_info(),
            headers,
            Ok(Json(WebhookBody {
                message: "hello".into(),
            })),
        )
        .await
        .into_response();

        assert_eq!(response.status(), StatusCode::UNAUTHORIZED);
        assert_eq!(provider_impl.calls.load(Ordering::SeqCst), 0);
    }

    #[tokio::test]
    async fn webhook_secret_hash_accepts_valid_header() {
        let provider_impl = Arc::new(MockProvider::default());
        let provider: Arc<dyn Provider> = provider_impl.clone();
        let memory: Arc<dyn Memory> = Arc::new(MockMemory);

        let state = AppState {
            config: Arc::new(Mutex::new(Config::default())),
            provider,
            model: "test-model".into(),
            temperature: 0.0,
            mem: memory,
            auto_save: false,
            webhook_secret_hash: Some(Arc::from(hash_webhook_secret("super-secret"))),
            pairing: Arc::new(PairingGuard::new(false, &[])),
            trust_forwarded_headers: false,
            rate_limiter: Arc::new(GatewayRateLimiter::new(100, 100, 100)),
            idempotency_store: Arc::new(IdempotencyStore::new(Duration::from_secs(300), 1000)),
            whatsapp: None,
            whatsapp_app_secret: None,
            observer: Arc::new(crate::observability::NoopObserver),
        };

        let mut headers = HeaderMap::new();
        headers.insert("X-Webhook-Secret", HeaderValue::from_static("super-secret"));

        let response = handle_webhook(
            State(state),
            test_connect_info(),
            headers,
            Ok(Json(WebhookBody {
                message: "hello".into(),
            })),
        )
        .await
        .into_response();

        assert_eq!(response.status(), StatusCode::OK);
        assert_eq!(provider_impl.calls.load(Ordering::SeqCst), 1);
    }

    // ══════════════════════════════════════════════════════════
    // WhatsApp Signature Verification Tests (CWE-345 Prevention)
    // ══════════════════════════════════════════════════════════

    fn compute_whatsapp_signature_hex(secret: &str, body: &[u8]) -> String {
        use hmac::{Hmac, Mac};
        use sha2::Sha256;

        let mut mac = Hmac::<Sha256>::new_from_slice(secret.as_bytes()).unwrap();
        mac.update(body);
        hex::encode(mac.finalize().into_bytes())
    }

    fn compute_whatsapp_signature_header(secret: &str, body: &[u8]) -> String {
        format!("sha256={}", compute_whatsapp_signature_hex(secret, body))
    }

    #[test]
    fn whatsapp_signature_valid() {
        // Test with known values
        let app_secret = "test_secret_key_12345";
        let body = b"test body content";

        let signature_header = compute_whatsapp_signature_header(app_secret, body);

        assert!(verify_whatsapp_signature(
            app_secret,
            body,
            &signature_header
        ));
    }

    #[test]
    fn whatsapp_signature_invalid_wrong_secret() {
        let app_secret = "correct_secret_key_abc";
        let wrong_secret = "wrong_secret_key_xyz";
        let body = b"test body content";

        let signature_header = compute_whatsapp_signature_header(wrong_secret, body);

        assert!(!verify_whatsapp_signature(
            app_secret,
            body,
            &signature_header
        ));
    }

    #[test]
    fn whatsapp_signature_invalid_wrong_body() {
        let app_secret = "test_secret_key_12345";
        let original_body = b"original body";
        let tampered_body = b"tampered body";

        let signature_header = compute_whatsapp_signature_header(app_secret, original_body);

        // Verify with tampered body should fail
        assert!(!verify_whatsapp_signature(
            app_secret,
            tampered_body,
            &signature_header
        ));
    }

    #[test]
    fn whatsapp_signature_missing_prefix() {
        let app_secret = "test_secret_key_12345";
        let body = b"test body";

        // Signature without "sha256=" prefix
        let signature_header = "abc123def456";

        assert!(!verify_whatsapp_signature(
            app_secret,
            body,
            signature_header
        ));
    }

    #[test]
    fn whatsapp_signature_empty_header() {
        let app_secret = "test_secret_key_12345";
        let body = b"test body";

        assert!(!verify_whatsapp_signature(app_secret, body, ""));
    }

    #[test]
    fn whatsapp_signature_invalid_hex() {
        let app_secret = "test_secret_key_12345";
        let body = b"test body";

        // Invalid hex characters
        let signature_header = "sha256=not_valid_hex_zzz";

        assert!(!verify_whatsapp_signature(
            app_secret,
            body,
            signature_header
        ));
    }

    #[test]
    fn whatsapp_signature_empty_body() {
        let app_secret = "test_secret_key_12345";
        let body = b"";

        let signature_header = compute_whatsapp_signature_header(app_secret, body);

        assert!(verify_whatsapp_signature(
            app_secret,
            body,
            &signature_header
        ));
    }

    #[test]
    fn whatsapp_signature_unicode_body() {
        let app_secret = "test_secret_key_12345";
        let body = "Hello 🦀 World".as_bytes();

        let signature_header = compute_whatsapp_signature_header(app_secret, body);

        assert!(verify_whatsapp_signature(
            app_secret,
            body,
            &signature_header
        ));
    }

    #[test]
    fn whatsapp_signature_json_payload() {
        let app_secret = "test_app_secret_key_xyz";
        let body = br#"{"entry":[{"changes":[{"value":{"messages":[{"from":"1234567890","text":{"body":"Hello"}}]}}]}]}"#;

        let signature_header = compute_whatsapp_signature_header(app_secret, body);

        assert!(verify_whatsapp_signature(
            app_secret,
            body,
            &signature_header
        ));
    }

    #[test]
    fn whatsapp_signature_case_sensitive_prefix() {
        let app_secret = "test_secret_key_12345";
        let body = b"test body";

        let hex_sig = compute_whatsapp_signature_hex(app_secret, body);

        // Wrong case prefix should fail
        let wrong_prefix = format!("SHA256={hex_sig}");
        assert!(!verify_whatsapp_signature(app_secret, body, &wrong_prefix));

        // Correct prefix should pass
        let correct_prefix = format!("sha256={hex_sig}");
        assert!(verify_whatsapp_signature(app_secret, body, &correct_prefix));
    }

    #[test]
    fn whatsapp_signature_truncated_hex() {
        let app_secret = "test_secret_key_12345";
        let body = b"test body";

        let hex_sig = compute_whatsapp_signature_hex(app_secret, body);
        let truncated = &hex_sig[..32]; // Only half the signature
        let signature_header = format!("sha256={truncated}");

        assert!(!verify_whatsapp_signature(
            app_secret,
            body,
            &signature_header
        ));
    }

    #[test]
    fn whatsapp_signature_extra_bytes() {
        let app_secret = "test_secret_key_12345";
        let body = b"test body";

        let hex_sig = compute_whatsapp_signature_hex(app_secret, body);
        let extended = format!("{hex_sig}deadbeef");
        let signature_header = format!("sha256={extended}");

        assert!(!verify_whatsapp_signature(
            app_secret,
            body,
            &signature_header
        ));
    }
}