diff --git a/core/archipelago/src/health_monitor.rs b/core/archipelago/src/health_monitor.rs
index 6c316e1e..7fe4c62a 100644
--- a/core/archipelago/src/health_monitor.rs
+++ b/core/archipelago/src/health_monitor.rs
@@ -147,14 +147,6 @@ pub fn spawn_health_monitor(state: Arc<StateManager>, data_dir: PathBuf) {
         loop {
             interval.tick().await;
 
-            // Check webhook config — if webhooks are disabled or ContainerCrash
-            // isn't subscribed, skip all health monitoring (no restarts, no notifications)
-            let webhook_config = webhooks::load_config(&data_dir).await.unwrap_or_default();
-            if !webhook_config.enabled || !webhook_config.events.contains(&WebhookEvent::ContainerCrash) {
-                debug!("Health monitor: skipping — webhooks disabled or ContainerCrash not subscribed");
-                continue;
-            }
-
             let containers = check_containers().await;
             if containers.is_empty() {
                 continue;
@@ -210,11 +202,26 @@ pub fn spawn_health_monitor(state: Arc<StateManager>, data_dir: PathBuf) {
                             };
 
                             // Keep only the latest 20 notifications
-                            data.notifications.push(notification);
+                            data.notifications.push(notification.clone());
                             if data.notifications.len() > 20 {
                                 data.notifications = data.notifications.split_off(data.notifications.len() - 20);
                             }
                             state_changed = true;
+
+                            // Fire-and-forget webhook delivery (checks config internally)
+                            let webhook_payload = webhooks::WebhookPayload {
+                                event: WebhookEvent::ContainerCrash,
+                                title: notification.title,
+                                message: notification.message,
+                                timestamp: notification.timestamp,
+                                node_id: String::new(),
+                                details: Some(serde_json::json!({
+                                    "container": container.name,
+                                    "app_id": container.app_id,
+                                    "state": container.state,
+                                })),
+                            };
+                            webhooks::send_webhook(&data_dir, webhook_payload).await;
                         }
                     }
                 }
diff --git a/loop/plan.md b/loop/plan.md
index 815c1a87..fd8816b9 100644
--- a/loop/plan.md
+++ b/loop/plan.md
@@ -468,7 +468,7 @@
 
 ### Sprint 40: Critical Fix & Identity Completion (April 2026 Week 1-2)
 
-- [ ] **WHFIX-01** — Decouple health monitor from webhook config. In `core/archipelago/src/health_monitor.rs` lines 150-156, the health check loop skips ALL monitoring (restarts + WebSocket notifications) when webhooks are disabled or ContainerCrash isn't subscribed. This means fresh installs (webhooks disabled by default) get NO auto-restart and NO UI notifications. Fix: remove the webhook config gate from the main loop. Health checks, auto-restarts, and WebSocket `Notification` pushes must run unconditionally. Move the webhook gate into a separate block that only controls external HTTP webhook delivery — call `webhooks::send_webhook()` only when enabled AND the event is subscribed. Keep the existing `send_webhook()` function which already checks `config.enabled` and `config.events.contains()` internally. **Acceptance**: With webhooks disabled (default), crash a container (`sudo podman stop archy-filebrowser`), confirm health monitor detects it within 60s, auto-restarts it, and pushes a Notification visible in the Dashboard toast. With webhooks enabled + URL configured, confirm HTTP POST is also sent. Deploy and verify on 192.168.1.228.
+- [x] **WHFIX-01** — Decouple health monitor from webhook config. In `core/archipelago/src/health_monitor.rs` lines 150-156, the health check loop skips ALL monitoring (restarts + WebSocket notifications) when webhooks are disabled or ContainerCrash isn't subscribed. This means fresh installs (webhooks disabled by default) get NO auto-restart and NO UI notifications. Fix: remove the webhook config gate from the main loop. Health checks, auto-restarts, and WebSocket `Notification` pushes must run unconditionally. Move the webhook gate into a separate block that only controls external HTTP webhook delivery — call `webhooks::send_webhook()` only when enabled AND the event is subscribed. Keep the existing `send_webhook()` function which already checks `config.enabled` and `config.events.contains()` internally. **Acceptance**: With webhooks disabled (default), crash a container (`sudo podman stop archy-filebrowser`), confirm health monitor detects it within 60s, auto-restarts it, and pushes a Notification visible in the Dashboard toast. With webhooks enabled + URL configured, confirm HTTP POST is also sent. Deploy and verify on 192.168.1.228.
 
 - [ ] **WHFIX-02** — Add monitoring.rs webhook integration. In `core/archipelago/src/monitoring/mod.rs`, the alert system pushes `Notification` to DataModel but never calls `webhooks::send_webhook()`. Add webhook delivery for fired alerts: when a `DiskWarning` alert fires, send `WebhookEvent::DiskWarning`; when `ContainerCrash` fires, send `WebhookEvent::ContainerCrash`. Map alert types to webhook events. The webhook call should be fire-and-forget (already is in `send_webhook`). **Acceptance**: Configure a webhook URL, trigger a disk warning (lower threshold temporarily to 1%), confirm HTTP POST received. Deploy and verify.