diff --git a/hosting/k8s/helm/Chart.yaml b/hosting/k8s/helm/Chart.yaml
index b003f5efe7e..15141244083 100644
--- a/hosting/k8s/helm/Chart.yaml
+++ b/hosting/k8s/helm/Chart.yaml
@@ -2,7 +2,7 @@ apiVersion: v2
 name: trigger
 description: The official Trigger.dev Helm chart
 type: application
-version: 4.5.7-plt663.9
+version: 4.5.7-plt663.10
 appVersion: v4.5.7
 home: https://trigger.dev
 sources:
diff --git a/hosting/k8s/helm/README.md b/hosting/k8s/helm/README.md
index c7608ddca25..23a5ac4f843 100644
--- a/hosting/k8s/helm/README.md
+++ b/hosting/k8s/helm/README.md
@@ -259,6 +259,27 @@ supervisor:
 
 The supervisor `extraVolumes` / `extraVolumeMounts` keys behave identically to the webapp ones. Both render unconditionally — they don't require any other feature toggle.
 
+### Supervisor init containers
+
+`supervisor.extraInitContainers` prepends init containers to the supervisor pod. It accepts a list, or a string that is `tpl`-rendered in chart scope (the same contract as `webapp.extraContainers`), so entries can use helpers such as `trigger-v4.fullname`.
+
+The supervisor makes one connect call to the webapp when it boots and exits 1 if that call fails; Kubernetes then restarts it with backoff. If your webapp is a single replica that runs migrations at boot, a node drain that reschedules both pods leaves the supervisor crash-looping until the webapp is back. Gating on the webapp health endpoint avoids the restarts:
+
+```yaml
+supervisor:
+  extraInitContainers: |
+    - name: wait-for-webapp
+      image: curlimages/curl:8.5.0
+      command: ["/bin/sh", "-c"]
+      args:
+        - |
+          until curl -sf http://{{ include "trigger-v4.fullname" . }}-webapp:{{ .Values.webapp.service.port }}/healthcheck; do
+            echo "webapp not ready"; sleep 5
+          done
+```
+
+The pod sits in `Init:0/1` (no restart counter) until the webapp answers, then the supervisor starts and connects normally.
+
 ### Worker pod security context
 
 By default the supervisor doesn't set a `securityContext` on the worker pods it schedules — it lets the cluster's PodSecurity admission / SCC apply whatever defaults are configured. If you need to enforce explicit pod- or container-level security, set:
diff --git a/hosting/k8s/helm/templates/supervisor.yaml b/hosting/k8s/helm/templates/supervisor.yaml
index 2a3b30e876e..533575127d5 100644
--- a/hosting/k8s/helm/templates/supervisor.yaml
+++ b/hosting/k8s/helm/templates/supervisor.yaml
@@ -76,8 +76,23 @@ spec:
         {{- with .Values.supervisor.podSecurityContext }}
         {{- toYaml . | nindent 8 }}
         {{- end }}
-      {{- if not .Values.webapp.bootstrap.enabled }}
+      {{- /*
+      extraInitContainers is tpl-rendered into a variable first (string or
+      list, same contract as webapp.extraContainers) so `initContainers:` is
+      only emitted when something actually renders — a template string that
+      evaluates to nothing would otherwise leave a null list behind.
+      */}}
+      {{- $extraInitContainers := "" }}
+      {{- with .Values.supervisor.extraInitContainers }}
+      {{- if kindIs "string" . }}
+      {{- $extraInitContainers = tpl . $ | trim }}
+      {{- else }}
+      {{- $extraInitContainers = tpl (toYaml .) $ | trim }}
+      {{- end }}
+      {{- end }}
+      {{- if or (not .Values.webapp.bootstrap.enabled) $extraInitContainers }}
       initContainers:
+        {{- if not .Values.webapp.bootstrap.enabled }}
         - name: init-shared
           image: busybox:1.35
           command: ['sh', '-c', 'mkdir -p /home/node/shared']
@@ -86,6 +101,10 @@ spec:
           volumeMounts:
             - name: shared
               mountPath: /home/node/shared
+        {{- end }}
+        {{- with $extraInitContainers }}
+        {{- . | nindent 8 }}
+        {{- end }}
       {{- end }}
       containers:
         - name: supervisor
diff --git a/hosting/k8s/helm/values.yaml b/hosting/k8s/helm/values.yaml
index ff539404b5f..afe58e3c528 100644
--- a/hosting/k8s/helm/values.yaml
+++ b/hosting/k8s/helm/values.yaml
@@ -419,6 +419,23 @@ supervisor:
     #   mountPath: /etc/ssl/enterprise-ca
     #   readOnly: true
 
+  # Extra init containers prepended to the Supervisor pod. Accepts a list,
+  # or a string that is tpl-rendered in chart scope (same contract as
+  # `webapp.extraContainers`), so entries can reference helpers and values.
+  #
+  # Typical use: gate supervisor start on the webapp's /healthcheck. The
+  # supervisor makes a single connect call to the webapp at boot and exits 1
+  # when it fails, so a webapp that is still running boot migrations turns
+  # into a supervisor CrashLoopBackOff. Waiting here keeps the pod in
+  # Init:0/1 (no restart counter) until the webapp answers.
+  extraInitContainers:
+    []
+    # - name: wait-for-webapp
+    #   image: curlimages/curl:8.5.0
+    #   command: ["/bin/sh", "-c"]
+    #   args:
+    #     - until curl -sf http://{{ include "trigger-v4.fullname" . }}-webapp:{{ .Values.webapp.service.port }}/healthcheck; do sleep 5; done
+
   # ServiceMonitor for Prometheus monitoring
   serviceMonitor:
     enabled: false