diff --git a/helm/templates/web-deployment.yaml b/helm/templates/web-deployment.yaml
index 74a9ed979..109f5d3d5 100644
--- a/helm/templates/web-deployment.yaml
+++ b/helm/templates/web-deployment.yaml
@@ -43,29 +43,6 @@ spec:
                   values:
                   - web
               topologyKey: "kubernetes.io/hostname"
-      initContainers:
-        - name: authentik-database-migrations
-          image: "{{ .Values.image.name }}:{{ .Values.image.tag }}"
-          imagePullPolicy: "{{ .Values.image.pullPolicy }}"
-          args: [migrate]
-          envFrom:
-            - configMapRef:
-                name: {{ include "authentik.fullname" . }}-config
-              prefix: AUTHENTIK_
-            - secretRef:
-                name: {{ include "authentik.fullname" . }}-secret-key
-              prefix: AUTHENTIK_
-          env:
-            - name: AUTHENTIK_REDIS__PASSWORD
-              valueFrom:
-                secretKeyRef:
-                  name: "{{ .Release.Name }}-redis"
-                  key: redis-password
-            - name: AUTHENTIK_POSTGRESQL__PASSWORD
-              valueFrom:
-                secretKeyRef:
-                  name: "{{ .Release.Name }}-postgresql"
-                  key: postgresql-password
       containers:
         - name: {{ .Chart.Name }}
           image: "{{ .Values.image.name }}:{{ .Values.image.tag }}"
diff --git a/lifecycle/bootstrap.sh b/lifecycle/bootstrap.sh
index 12eec0a6e..d4e318c1f 100755
--- a/lifecycle/bootstrap.sh
+++ b/lifecycle/bootstrap.sh
@@ -2,13 +2,13 @@
 python -m lifecycle.wait_for_db
 printf '{"event": "Bootstrap completed", "level": "info", "logger": "bootstrap", "command": "%s"}\n' "$@" > /dev/stderr
 if [[ "$1" == "server" ]]; then
+    python -m lifecycle.migrate
     gunicorn -c /lifecycle/gunicorn.conf.py authentik.root.asgi:application
 elif [[ "$1" == "worker" ]]; then
     celery -A authentik.root.celery worker --autoscale 3,1 -E -B -s /tmp/celerybeat-schedule -Q authentik,authentik_scheduled,authentik_events
 elif [[ "$1" == "migrate" ]]; then
-    # Run system migrations first, run normal migrations after
+    printf "DEPERECATED: database migrations are now executed automatically on startup."
     python -m lifecycle.migrate
-    python -m manage migrate
 elif [[ "$1" == "backup" ]]; then
     python -m manage dbbackup --clean
 elif [[ "$1" == "restore" ]]; then
diff --git a/lifecycle/migrate.py b/lifecycle/migrate.py
index 75ad665a0..3ce9c71ab 100755
--- a/lifecycle/migrate.py
+++ b/lifecycle/migrate.py
@@ -1,5 +1,6 @@
 #!/usr/bin/env python
 """System Migration handler"""
+import os
 from importlib.util import module_from_spec, spec_from_file_location
 from inspect import getmembers, isclass
 from pathlib import Path
@@ -11,6 +12,7 @@ from structlog.stdlib import get_logger
 from authentik.lib.config import CONFIG
 
 LOGGER = get_logger()
+ADV_LOCK_UID = 1000
 
 
 class BaseMigration:
@@ -40,18 +42,36 @@ if __name__ == "__main__":
         host=CONFIG.y("postgresql.host"),
     )
     curr = conn.cursor()
+    # lock an advisory lock to prevent multiple instances from migrating at once
+    LOGGER.info("waiting to acquire database lock")
+    curr.execute("SELECT pg_advisory_lock(%s)", (ADV_LOCK_UID,))
+    try:
+        for migration in (
+            Path(__file__).parent.absolute().glob("system_migrations/*.py")
+        ):
+            spec = spec_from_file_location("lifecycle.system_migrations", migration)
+            mod = module_from_spec(spec)
+            # pyright: reportGeneralTypeIssues=false
+            spec.loader.exec_module(mod)
 
-    for migration in Path(__file__).parent.absolute().glob("system_migrations/*.py"):
-        spec = spec_from_file_location("lifecycle.system_migrations", migration)
-        mod = module_from_spec(spec)
-        # pyright: reportGeneralTypeIssues=false
-        spec.loader.exec_module(mod)
-
-        for name, sub in getmembers(mod, isclass):
-            if name != "Migration":
-                continue
-            migration = sub(curr, conn)
-            if migration.needs_migration():
-                LOGGER.info("Migration needs to be applied", migration=sub)
-                migration.run()
-                LOGGER.info("Migration finished applying", migration=sub)
+            for name, sub in getmembers(mod, isclass):
+                if name != "Migration":
+                    continue
+                migration = sub(curr, conn)
+                if migration.needs_migration():
+                    LOGGER.info("Migration needs to be applied", migration=sub)
+                    migration.run()
+                    LOGGER.info("Migration finished applying", migration=sub)
+        LOGGER.info("applying django migrations")
+        os.environ.setdefault("DJANGO_SETTINGS_MODULE", "authentik.root.settings")
+        try:
+            from django.core.management import execute_from_command_line
+        except ImportError as exc:
+            raise ImportError(
+                "Couldn't import Django. Are you sure it's installed and "
+                "available on your PYTHONPATH environment variable? Did you "
+                "forget to activate a virtual environment?"
+            ) from exc
+        execute_from_command_line(["", "migrate"])
+    finally:
+        curr.execute("SELECT pg_advisory_unlock(%s)", (ADV_LOCK_UID,))