diff --git a/backend/app/services/webhooks/__init__.py b/backend/app/services/webhooks/__init__.py
index d4c7fc60..38aefa4b 100644
--- a/backend/app/services/webhooks/__init__.py
+++ b/backend/app/services/webhooks/__init__.py
@@ -1,3 +1,22 @@
-"""Webhook queueing and dispatch utilities."""
+"""Webhook queueing + dispatch utilities.
 
-__all__ = ["dispatch", "queue", "scheduler"]
+Prefer importing from this package when used by other modules.
+"""
+
+from app.services.webhooks.dispatch import run_flush_webhook_delivery_queue
+from app.services.webhooks.queue import (
+    QueuedWebhookDelivery,
+    dequeue_webhook_delivery,
+    enqueue_webhook_delivery,
+    requeue_if_failed,
+)
+from app.services.webhooks.scheduler import bootstrap_webhook_dispatch_schedule
+
+__all__ = [
+    "QueuedWebhookDelivery",
+    "bootstrap_webhook_dispatch_schedule",
+    "dequeue_webhook_delivery",
+    "enqueue_webhook_delivery",
+    "requeue_if_failed",
+    "run_flush_webhook_delivery_queue",
+]
diff --git a/backend/app/services/webhooks/scheduler.py b/backend/app/services/webhooks/scheduler.py
index d96744f3..df24c9ba 100644
--- a/backend/app/services/webhooks/scheduler.py
+++ b/backend/app/services/webhooks/scheduler.py
@@ -1,24 +1,34 @@
-"""Webhook dispatch scheduler bootstrap for rq-scheduler."""
+"""Webhook dispatch scheduler bootstrap for rq-scheduler.
+
+This module is typically run once at container start to ensure the recurring
+job exists (idempotent registration).
+"""
 
 from __future__ import annotations
 
+import time
 from datetime import datetime, timedelta, timezone
 
 from redis import Redis
 from rq_scheduler import Scheduler  # type: ignore[import-untyped]
 
 from app.core.config import settings
-from app.services.webhooks import dispatch
+from app.core.logging import get_logger
+from app.services.webhooks.dispatch import run_flush_webhook_delivery_queue
+
+logger = get_logger(__name__)
 
 
-def bootstrap_webhook_dispatch_schedule(interval_seconds: int | None = None) -> None:
-    """Register a recurring queue-flush job and keep it idempotent."""
-    connection = Redis.from_url(settings.webhook_redis_url)
-    scheduler = Scheduler(queue_name=settings.webhook_queue_name, connection=connection)
+def bootstrap_webhook_dispatch_schedule(
+    interval_seconds: int | None = None,
+    *,
+    max_attempts: int = 5,
+    retry_sleep_seconds: float = 1.0,
+) -> None:
+    """Register a recurring queue-flush job and keep it idempotent.
 
-    for job in scheduler.get_jobs():
-        if job.id == settings.webhook_dispatch_schedule_id:
-            scheduler.cancel(job)
+    Retries Redis connectivity to avoid crashing on transient startup ordering.
+    """
 
     effective_interval_seconds = (
         settings.webhook_dispatch_schedule_interval_seconds
@@ -26,11 +36,48 @@ def bootstrap_webhook_dispatch_schedule(interval_seconds: int | None = None) ->
         else interval_seconds
     )
 
-    scheduler.schedule(
-        datetime.now(tz=timezone.utc) + timedelta(seconds=5),
-        func=dispatch.run_flush_webhook_delivery_queue,
-        interval=effective_interval_seconds,
-        repeat=None,
-        id=settings.webhook_dispatch_schedule_id,
-        queue_name=settings.webhook_queue_name,
-    )
+    last_exc: Exception | None = None
+    for attempt in range(1, max_attempts + 1):
+        try:
+            connection = Redis.from_url(settings.webhook_redis_url)
+            connection.ping()
+            scheduler = Scheduler(
+                queue_name=settings.webhook_queue_name,
+                connection=connection,
+            )
+
+            for job in scheduler.get_jobs():
+                if job.id == settings.webhook_dispatch_schedule_id:
+                    scheduler.cancel(job)
+
+            scheduler.schedule(
+                datetime.now(tz=timezone.utc) + timedelta(seconds=5),
+                func=run_flush_webhook_delivery_queue,
+                interval=effective_interval_seconds,
+                repeat=None,
+                id=settings.webhook_dispatch_schedule_id,
+                queue_name=settings.webhook_queue_name,
+            )
+            logger.info(
+                "webhook.scheduler.bootstrapped",
+                extra={
+                    "schedule_id": settings.webhook_dispatch_schedule_id,
+                    "queue_name": settings.webhook_queue_name,
+                    "interval_seconds": effective_interval_seconds,
+                },
+            )
+            return
+        except Exception as exc:
+            last_exc = exc
+            logger.warning(
+                "webhook.scheduler.bootstrap_failed",
+                extra={
+                    "attempt": attempt,
+                    "max_attempts": max_attempts,
+                    "error": str(exc),
+                },
+            )
+            if attempt < max_attempts:
+                time.sleep(retry_sleep_seconds * attempt)
+
+    raise RuntimeError("Failed to bootstrap webhook dispatch schedule") from last_exc
diff --git a/compose.yml b/compose.yml
index 9d97674e..12bc95d5 100644
--- a/compose.yml
+++ b/compose.yml
@@ -104,7 +104,7 @@ services:
       WEBHOOK_REDIS_URL: redis://redis:6379/0
       WEBHOOK_QUEUE_NAME: webhook-dispatch
       WEBHOOK_DISPATCH_SCHEDULE_ID: webhook-dispatch-batch
-      WEBHOOK_DISPATCH_SCHEDULE_INTERVAL_SECONDS: 900
+      WEBHOOK_DISPATCH_SCHEDULE_INTERVAL_SECONDS: ${WEBHOOK_DISPATCH_SCHEDULE_INTERVAL_SECONDS:-900}
     restart: unless-stopped
 
 volumes: