README.md

@@ -496,9 +496,11 @@ External Service
                                         ┌──────────────┐
                                         │  Delivery    │◄── retry timers
                                         │  Engine      │    (backoff)
+                                        │  (worker     │
+                                        │   pool)      │
                                         └──────┬───────┘
                                                │
-                              ┌─── parallel goroutines (fan-out) ───┐
+                              ┌── bounded worker pool (N workers) ──┐
                               ▼                ▼                    ▼
                        ┌────────────┐   ┌────────────┐      ┌────────────┐
                        │ HTTP Target│   │Retry Target│      │ Log Target │
@@ -508,28 +510,56 @@ External Service
                                         └────────────┘
 ```
 
-### Parallel Fan-Out Delivery
+### Bounded Worker Pool
 
-When the delivery engine receives a batch of tasks for an event, it
-fans out **all targets in parallel** — each `DeliveryTask` is dispatched
-in its own goroutine immediately. An HTTP target, a retry target, and
-a log target for the same event all start delivering simultaneously
-with no sequential bottleneck.
+The delivery engine uses a **fixed-size worker pool** (default: 10
+workers) to process all deliveries. At most N deliveries are in-flight
+at any time, preventing goroutine explosions regardless of queue depth.
+
+**Architecture:**
+
+- **Channels as queues:** Two buffered channels serve as bounded queues:
+  a delivery channel (new tasks from the webhook handler) and a retry
+  channel (tasks from backoff timers). Both are buffered to 10,000.
+- **Fan-out via channel, not goroutines:** When an event arrives with
+  multiple targets, each `DeliveryTask` is sent to the delivery channel.
+  Workers pick them up and process them — no goroutine-per-target.
+- **Worker goroutines:** A fixed number of worker goroutines select from
+  both channels. Each worker processes one task at a time, then picks up
+  the next. Workers are the ONLY goroutines doing actual HTTP delivery.
+- **Retry backpressure with DB fallback:** When a retry timer fires and
+  the retry channel is full, the timer is dropped — the delivery stays
+  in `retrying` status in the database. A periodic sweep (every 60s)
+  scans for these "orphaned" retries and re-queues them. No blocked
+  goroutines, no unbounded timer chains.
+- **Bounded concurrency:** At most N deliveries (N = number of workers)
+  are in-flight simultaneously. Even if a circuit breaker is open for
+  hours and thousands of retries queue up in the channels, the workers
+  drain them at a controlled rate when the circuit closes.
 
 This means:
 
-- **No head-of-line blocking** — a slow HTTP target doesn't delay the
-  log target or other targets.
-- **Maximum throughput** — all targets receive the event as quickly as
-  possible.
-- **Independent results** — each goroutine records its own delivery
-  result in the per-webhook database without coordination.
-- **Fire-and-forget** — the engine doesn't wait for all goroutines to
-  finish; each delivery is completely independent.
+- **No goroutine explosion** — even with 10,000 queued retries, only
+  N worker goroutines exist.
+- **Natural backpressure** — if workers are busy, new tasks wait in the
+  channel buffer rather than spawning more goroutines.
+- **Independent results** — each worker records its own delivery result
+  in the per-webhook database without coordination.
+- **Graceful shutdown** — cancel the context, workers finish their
+  current task and exit. `WaitGroup.Wait()` ensures clean shutdown.
 
-The same parallel fan-out applies to crash recovery: when the engine
-restarts and finds pending deliveries in per-webhook databases, it
-recovers them and fans them out in parallel just like fresh deliveries.
+**Recovery paths:**
+
+1. **Startup recovery:** When the engine starts, it scans all per-webhook
+   databases for `pending` and `retrying` deliveries. Pending deliveries
+   are sent to the delivery channel; retrying deliveries get backoff
+   timers scheduled.
+2. **Periodic retry sweep (DB-mediated fallback):** Every 60 seconds the
+   engine scans for `retrying` deliveries whose backoff period has
+   elapsed. This catches "orphaned" retries — ones whose in-memory timer
+   was dropped because the retry channel was full. The database is the
+   durable fallback that ensures no retry is permanently lost, even under
+   extreme backpressure.
 
 ### Circuit Breaker (Retry Targets)
 

internal/delivery/engine.go

@@ -18,13 +18,26 @@ import (
 )
 
 const (
-	// notifyChannelSize is the buffer size for the delivery notification channel.
-	// Sized large enough that the webhook handler should never block.
-	notifyChannelSize = 1000
+	// deliveryChannelSize is the buffer size for the delivery channel.
+	// New DeliveryTasks from the webhook handler are sent here. Workers
+	// drain this channel. Sized large enough that the webhook handler
+	// should never block under normal load.
+	deliveryChannelSize = 10000
 
-	// retryChannelSize is the buffer size for the retry channel. Timer-fired
-	// retries are sent here for processing by the engine goroutine.
-	retryChannelSize = 1000
+	// retryChannelSize is the buffer size for the retry channel.
+	// Timer-fired retries are sent here for processing by workers.
+	retryChannelSize = 10000
+
+	// defaultWorkers is the number of worker goroutines in the delivery
+	// engine pool. At most this many deliveries are in-flight at any
+	// time, preventing goroutine explosions regardless of queue depth.
+	defaultWorkers = 10
+
+	// retrySweepInterval is how often the periodic retry sweep runs.
+	// The sweep scans all per-webhook databases for "orphaned" retrying
+	// deliveries — ones whose in-memory timer was dropped because the
+	// retry channel was full. This is the DB-mediated fallback path.
+	retrySweepInterval = 60 * time.Second
 
 	// MaxInlineBodySize is the maximum event body size that will be carried
 	// inline in a DeliveryTask through the channel. Bodies at or above this
@@ -94,30 +107,30 @@ type EngineParams struct {
 	Logger    *logger.Logger
 }
 
-// Engine processes queued deliveries in the background using an
-// event-driven architecture. New deliveries arrive as self-contained
-// DeliveryTask slices via a buffered channel from the webhook handler.
-// In the happy path (body ≤ 16KB), the engine delivers without reading
-// from any database — it only writes to record results. Failed deliveries
-// that need retry are scheduled via Go timers with exponential backoff;
-// each timer fires into a separate retry channel carrying the full
-// DeliveryTask so retries also avoid unnecessary DB reads. The database
-// stores delivery status for crash recovery only; on startup the engine
-// scans for interrupted deliveries and re-queues them.
+// Engine processes queued deliveries in the background using a bounded
+// worker pool architecture. New deliveries arrive as individual
+// DeliveryTask values via a buffered delivery channel from the webhook
+// handler. Failed deliveries that need retry are scheduled via Go timers
+// with exponential backoff; each timer fires into a separate retry
+// channel. A fixed number of worker goroutines drain both channels,
+// ensuring at most N deliveries are in-flight at any time (N = number
+// of workers). This prevents goroutine explosions when a circuit breaker
+// is open for a long period and many retries queue up.
 //
-// All targets for a single event are delivered in parallel — each
-// DeliveryTask is dispatched in its own goroutine for maximum fan-out
-// speed. Retry targets are protected by a per-target circuit breaker
-// that stops hammering a down target after consecutive failures.
+// In the happy path (body ≤ 16KB), a worker delivers without reading
+// from any database — it only writes to record results. The database
+// stores delivery status for crash recovery only; on startup the engine
+// scans for interrupted deliveries and re-queues them into the channels.
 type Engine struct {
-	database  *database.Database
-	dbManager *database.WebhookDBManager
-	log       *slog.Logger
-	client    *http.Client
-	cancel    context.CancelFunc
-	wg        sync.WaitGroup
-	notifyCh  chan []DeliveryTask
-	retryCh   chan DeliveryTask
+	database   *database.Database
+	dbManager  *database.WebhookDBManager
+	log        *slog.Logger
+	client     *http.Client
+	cancel     context.CancelFunc
+	wg         sync.WaitGroup
+	deliveryCh chan DeliveryTask
+	retryCh    chan DeliveryTask
+	workers    int
 
 	// circuitBreakers stores a *CircuitBreaker per target ID. Only used
 	// for retry targets — HTTP, database, and log targets do not need
@@ -134,8 +147,9 @@ func New(lc fx.Lifecycle, params EngineParams) *Engine {
 		client: &http.Client{
 			Timeout: httpClientTimeout,
 		},
-		notifyCh: make(chan []DeliveryTask, notifyChannelSize),
-		retryCh:  make(chan DeliveryTask, retryChannelSize),
+		deliveryCh: make(chan DeliveryTask, deliveryChannelSize),
+		retryCh:    make(chan DeliveryTask, retryChannelSize),
+		workers:    defaultWorkers,
 	}
 
 	lc.Append(fx.Hook{
@@ -155,9 +169,25 @@ func New(lc fx.Lifecycle, params EngineParams) *Engine {
 func (e *Engine) start() {
 	ctx, cancel := context.WithCancel(context.Background())
 	e.cancel = cancel
+
+	// Start the worker pool. These are the ONLY goroutines that
+	// perform HTTP delivery. Bounded concurrency is guaranteed.
+	for i := 0; i < e.workers; i++ {
+		e.wg.Add(1)
+		go e.worker(ctx)
+	}
+
+	// Start recovery scan in a separate goroutine. Recovered tasks
+	// are sent into the delivery/retry channels and picked up by workers.
 	e.wg.Add(1)
-	go e.run(ctx)
-	e.log.Info("delivery engine started")
+	go e.recoverPending(ctx)
+
+	// Start the periodic retry sweep. This is the DB-mediated fallback
+	// for retries whose timers were dropped due to channel overflow.
+	e.wg.Add(1)
+	go e.retrySweep(ctx)
+
+	e.log.Info("delivery engine started", "workers", e.workers)
 }
 
 func (e *Engine) stop() {
@@ -170,43 +200,191 @@ func (e *Engine) stop() {
 // Notify signals the delivery engine that new deliveries are ready.
 // Called by the webhook handler after creating delivery records. Each
 // DeliveryTask carries all data needed for delivery in the ≤16KB case.
-// The call is non-blocking; if the channel is full, a warning is logged
-// and the deliveries will be recovered on the next engine restart.
+// Tasks are sent individually to the delivery channel. The call is
+// non-blocking; if the channel is full, a warning is logged and the
+// delivery will be recovered on the next engine restart.
 func (e *Engine) Notify(tasks []DeliveryTask) {
-	select {
-	case e.notifyCh <- tasks:
-	default:
-		e.log.Warn("delivery notification channel full, deliveries will be recovered on restart",
-			"task_count", len(tasks),
-		)
-	}
-}
-
-func (e *Engine) run(ctx context.Context) {
-	defer e.wg.Done()
-
-	// On startup, recover any pending or retrying deliveries that were
-	// interrupted by an unexpected shutdown. Pending deliveries are
-	// processed immediately; retrying deliveries get timers scheduled
-	// for their remaining backoff.
-	e.recoverInFlight(ctx)
-
-	for {
+	for i := range tasks {
 		select {
-		case <-ctx.Done():
-			return
-		case tasks := <-e.notifyCh:
-			e.processDeliveryTasks(ctx, tasks)
-		case task := <-e.retryCh:
-			e.processRetryTask(ctx, task)
+		case e.deliveryCh <- tasks[i]:
+		default:
+			e.log.Warn("delivery channel full, task will be recovered on restart",
+				"delivery_id", tasks[i].DeliveryID,
+				"event_id", tasks[i].EventID,
+			)
 		}
 	}
 }
 
+// worker is the main loop for a worker goroutine. It selects from both
+// the delivery channel (new tasks from the handler) and the retry channel
+// (tasks from backoff timers). At most e.workers deliveries are in-flight
+// at any time.
+func (e *Engine) worker(ctx context.Context) {
+	defer e.wg.Done()
+	for {
+		select {
+		case <-ctx.Done():
+			return
+		case task := <-e.deliveryCh:
+			e.processNewTask(ctx, &task)
+		case task := <-e.retryCh:
+			e.processRetryTask(ctx, &task)
+		}
+	}
+}
+
+// recoverPending runs on startup to recover any pending or retrying
+// deliveries that were interrupted by an unexpected shutdown. Recovered
+// tasks are sent into the delivery/retry channels for workers to pick up.
+func (e *Engine) recoverPending(ctx context.Context) {
+	defer e.wg.Done()
+	e.recoverInFlight(ctx)
+}
+
+// processNewTask handles a single new delivery task from the delivery
+// channel. It builds the event and target context from the task's inline
+// data and executes the delivery. For large bodies (≥ MaxInlineBodySize),
+// the body is fetched from the per-webhook database on demand.
+func (e *Engine) processNewTask(ctx context.Context, task *DeliveryTask) {
+	webhookDB, err := e.dbManager.GetDB(task.WebhookID)
+	if err != nil {
+		e.log.Error("failed to get webhook database",
+			"webhook_id", task.WebhookID,
+			"error", err,
+		)
+		return
+	}
+
+	// Build Event from task data
+	event := database.Event{
+		Method:      task.Method,
+		Headers:     task.Headers,
+		ContentType: task.ContentType,
+	}
+	event.ID = task.EventID
+	event.WebhookID = task.WebhookID
+
+	if task.Body != nil {
+		event.Body = *task.Body
+	} else {
+		// Large body: fetch from per-webhook DB
+		var dbEvent database.Event
+		if err := webhookDB.Select("body").
+			First(&dbEvent, "id = ?", task.EventID).Error; err != nil {
+			e.log.Error("failed to fetch event body from database",
+				"event_id", task.EventID,
+				"error", err,
+			)
+			return
+		}
+		event.Body = dbEvent.Body
+	}
+
+	// Build Target from task data (no main DB query needed)
+	target := database.Target{
+		Name:       task.TargetName,
+		Type:       task.TargetType,
+		Config:     task.TargetConfig,
+		MaxRetries: task.MaxRetries,
+	}
+	target.ID = task.TargetID
+
+	// Build Delivery struct for the processing chain
+	d := &database.Delivery{
+		EventID:  task.EventID,
+		TargetID: task.TargetID,
+		Status:   database.DeliveryStatusPending,
+		Event:    event,
+		Target:   target,
+	}
+	d.ID = task.DeliveryID
+
+	e.processDelivery(ctx, webhookDB, d, task)
+}
+
+// processRetryTask handles a single delivery task fired by a retry timer.
+// The task carries all data needed for delivery (same as the initial
+// notification). The only DB read is a status check to verify the delivery
+// hasn't been cancelled or resolved while the timer was pending.
+func (e *Engine) processRetryTask(ctx context.Context, task *DeliveryTask) {
+	webhookDB, err := e.dbManager.GetDB(task.WebhookID)
+	if err != nil {
+		e.log.Error("failed to get webhook database for retry",
+			"webhook_id", task.WebhookID,
+			"delivery_id", task.DeliveryID,
+			"error", err,
+		)
+		return
+	}
+
+	// Verify delivery is still in retrying status (may have been
+	// cancelled or manually resolved while the timer was pending)
+	var d database.Delivery
+	if err := webhookDB.Select("id", "status").
+		First(&d, "id = ?", task.DeliveryID).Error; err != nil {
+		e.log.Error("failed to load delivery for retry",
+			"delivery_id", task.DeliveryID,
+			"error", err,
+		)
+		return
+	}
+
+	if d.Status != database.DeliveryStatusRetrying {
+		e.log.Debug("skipping retry for delivery no longer in retrying status",
+			"delivery_id", d.ID,
+			"status", d.Status,
+		)
+		return
+	}
+
+	// Build Event from task data
+	event := database.Event{
+		Method:      task.Method,
+		Headers:     task.Headers,
+		ContentType: task.ContentType,
+	}
+	event.ID = task.EventID
+	event.WebhookID = task.WebhookID
+
+	if task.Body != nil {
+		event.Body = *task.Body
+	} else {
+		// Large body: fetch from per-webhook DB
+		var dbEvent database.Event
+		if err := webhookDB.Select("body").
+			First(&dbEvent, "id = ?", task.EventID).Error; err != nil {
+			e.log.Error("failed to fetch event body for retry",
+				"event_id", task.EventID,
+				"error", err,
+			)
+			return
+		}
+		event.Body = dbEvent.Body
+	}
+
+	// Build Target from task data
+	target := database.Target{
+		Name:       task.TargetName,
+		Type:       task.TargetType,
+		Config:     task.TargetConfig,
+		MaxRetries: task.MaxRetries,
+	}
+	target.ID = task.TargetID
+
+	// Populate the delivery with event and target for processing
+	d.EventID = task.EventID
+	d.TargetID = task.TargetID
+	d.Event = event
+	d.Target = target
+
+	e.processDelivery(ctx, webhookDB, &d, task)
+}
+
 // recoverInFlight scans all webhooks on startup for deliveries that were
-// interrupted by an unexpected shutdown. Pending deliveries are processed
-// immediately; retrying deliveries get timers scheduled for their
-// remaining backoff period.
+// interrupted by an unexpected shutdown. Pending deliveries are sent to
+// the delivery channel; retrying deliveries get timers scheduled for
+// their remaining backoff period.
 func (e *Engine) recoverInFlight(ctx context.Context) {
 	var webhookIDs []string
 	if err := e.database.DB().Model(&database.Webhook{}).Pluck("id", &webhookIDs).Error; err != nil {
@@ -230,9 +408,8 @@ func (e *Engine) recoverInFlight(ctx context.Context) {
 }
 
 // recoverWebhookDeliveries recovers pending and retrying deliveries for
-// a single webhook. This is the recovery path — it reads everything from
-// the database since there are no in-memory notifications available after
-// a restart.
+// a single webhook. Pending deliveries are sent to the delivery channel;
+// retrying deliveries get timers scheduled for their remaining backoff.
 func (e *Engine) recoverWebhookDeliveries(ctx context.Context, webhookID string) {
 	webhookDB, err := e.dbManager.GetDB(webhookID)
 	if err != nil {
@@ -243,19 +420,8 @@ func (e *Engine) recoverWebhookDeliveries(ctx context.Context, webhookID string)
 		return
 	}
 
-	// Check for pending deliveries and process them immediately
-	var pendingCount int64
-	webhookDB.Model(&database.Delivery{}).
-		Where("status = ?", database.DeliveryStatusPending).
-		Count(&pendingCount)
-
-	if pendingCount > 0 {
-		e.log.Info("recovering pending deliveries",
-			"webhook_id", webhookID,
-			"count", pendingCount,
-		)
-		e.processWebhookPendingDeliveries(ctx, webhookID)
-	}
+	// Recover pending deliveries by sending them to the delivery channel
+	e.recoverPendingDeliveries(ctx, webhookDB, webhookID)
 
 	// Schedule timers for retrying deliveries based on remaining backoff
 	var retrying []database.Delivery
@@ -356,201 +522,11 @@ func (e *Engine) recoverWebhookDeliveries(ctx context.Context, webhookID string)
 	}
 }
 
-// processDeliveryTasks handles a batch of delivery tasks from the webhook
-// handler. Each task is dispatched in its own goroutine for parallel
-// fan-out — all targets for a single event start delivering simultaneously.
-// In the happy path (body ≤ 16KB), the engine delivers without reading
-// from any database — it trusts the handler's inline data and only touches
-// the DB to record results. For large bodies (body > 16KB), the body is
-// fetched once and shared across all goroutines in the batch.
-func (e *Engine) processDeliveryTasks(ctx context.Context, tasks []DeliveryTask) {
-	if len(tasks) == 0 {
-		return
-	}
-
-	// All tasks in a batch share the same webhook ID
-	webhookID := tasks[0].WebhookID
-	webhookDB, err := e.dbManager.GetDB(webhookID)
-	if err != nil {
-		e.log.Error("failed to get webhook database",
-			"webhook_id", webhookID,
-			"error", err,
-		)
-		return
-	}
-
-	// For the large-body case, pre-fetch the event body once before
-	// fanning out so all goroutines share the same data.
-	var fetchedBody *string
-	if tasks[0].Body == nil {
-		var dbEvent database.Event
-		if err := webhookDB.Select("body").
-			First(&dbEvent, "id = ?", tasks[0].EventID).Error; err != nil {
-			e.log.Error("failed to fetch event body from database",
-				"event_id", tasks[0].EventID,
-				"error", err,
-			)
-			return
-		}
-		fetchedBody = &dbEvent.Body
-	}
-
-	// Fan out: spin up a goroutine per task for parallel delivery.
-	// Each goroutine is independent (fire-and-forget) and records its
-	// own result. No need to wait for all goroutines to finish.
-	for i := range tasks {
-		select {
-		case <-ctx.Done():
-			return
-		default:
-		}
-
-		task := tasks[i] // copy for goroutine closure safety
-
-		go func() {
-			e.deliverTask(ctx, webhookDB, &task, fetchedBody)
-		}()
-	}
-}
-
-// deliverTask prepares and executes a single delivery task. Called from
-// a dedicated goroutine for parallel fan-out.
-func (e *Engine) deliverTask(ctx context.Context, webhookDB *gorm.DB, task *DeliveryTask, fetchedBody *string) {
-	// Build Event from task data
-	event := database.Event{
-		Method:      task.Method,
-		Headers:     task.Headers,
-		ContentType: task.ContentType,
-	}
-	event.ID = task.EventID
-	event.WebhookID = task.WebhookID
-
-	switch {
-	case task.Body != nil:
-		event.Body = *task.Body
-	case fetchedBody != nil:
-		event.Body = *fetchedBody
-	default:
-		e.log.Error("no body available for delivery task",
-			"delivery_id", task.DeliveryID,
-			"event_id", task.EventID,
-		)
-		return
-	}
-
-	// Build Target from task data (no main DB query needed)
-	target := database.Target{
-		Name:       task.TargetName,
-		Type:       task.TargetType,
-		Config:     task.TargetConfig,
-		MaxRetries: task.MaxRetries,
-	}
-	target.ID = task.TargetID
-
-	// Build Delivery struct for the processing chain
-	d := &database.Delivery{
-		EventID:  task.EventID,
-		TargetID: task.TargetID,
-		Status:   database.DeliveryStatusPending,
-		Event:    event,
-		Target:   target,
-	}
-	d.ID = task.DeliveryID
-
-	e.processDelivery(ctx, webhookDB, d, task)
-}
-
-// processRetryTask handles a single delivery task fired by a retry timer.
-// The task carries all data needed for delivery (same as the initial
-// notification). The only DB read is a status check to verify the delivery
-// hasn't been cancelled or resolved while the timer was pending.
-func (e *Engine) processRetryTask(ctx context.Context, task DeliveryTask) {
-	webhookDB, err := e.dbManager.GetDB(task.WebhookID)
-	if err != nil {
-		e.log.Error("failed to get webhook database for retry",
-			"webhook_id", task.WebhookID,
-			"delivery_id", task.DeliveryID,
-			"error", err,
-		)
-		return
-	}
-
-	// Verify delivery is still in retrying status (may have been
-	// cancelled or manually resolved while the timer was pending)
-	var d database.Delivery
-	if err := webhookDB.Select("id", "status").
-		First(&d, "id = ?", task.DeliveryID).Error; err != nil {
-		e.log.Error("failed to load delivery for retry",
-			"delivery_id", task.DeliveryID,
-			"error", err,
-		)
-		return
-	}
-
-	if d.Status != database.DeliveryStatusRetrying {
-		e.log.Debug("skipping retry for delivery no longer in retrying status",
-			"delivery_id", d.ID,
-			"status", d.Status,
-		)
-		return
-	}
-
-	// Build Event from task data
-	event := database.Event{
-		Method:      task.Method,
-		Headers:     task.Headers,
-		ContentType: task.ContentType,
-	}
-	event.ID = task.EventID
-	event.WebhookID = task.WebhookID
-
-	if task.Body != nil {
-		event.Body = *task.Body
-	} else {
-		// Large body: fetch from per-webhook DB
-		var dbEvent database.Event
-		if err := webhookDB.Select("body").
-			First(&dbEvent, "id = ?", task.EventID).Error; err != nil {
-			e.log.Error("failed to fetch event body for retry",
-				"event_id", task.EventID,
-				"error", err,
-			)
-			return
-		}
-		event.Body = dbEvent.Body
-	}
-
-	// Build Target from task data
-	target := database.Target{
-		Name:       task.TargetName,
-		Type:       task.TargetType,
-		Config:     task.TargetConfig,
-		MaxRetries: task.MaxRetries,
-	}
-	target.ID = task.TargetID
-
-	// Populate the delivery with event and target for processing
-	d.EventID = task.EventID
-	d.TargetID = task.TargetID
-	d.Event = event
-	d.Target = target
-
-	e.processDelivery(ctx, webhookDB, &d, &task)
-}
-
-// processWebhookPendingDeliveries queries a single webhook's database for
-// all pending deliveries and processes them. Used for crash recovery where
-// we don't have in-memory notifications — everything is loaded from the DB.
-func (e *Engine) processWebhookPendingDeliveries(ctx context.Context, webhookID string) {
-	webhookDB, err := e.dbManager.GetDB(webhookID)
-	if err != nil {
-		e.log.Error("failed to get webhook database",
-			"webhook_id", webhookID,
-			"error", err,
-		)
-		return
-	}
-
+// recoverPendingDeliveries sends pending deliveries for a single webhook
+// into the delivery channel. Used for crash recovery where we don't have
+// in-memory notifications — everything is loaded from the DB and queued
+// for workers to pick up.
+func (e *Engine) recoverPendingDeliveries(ctx context.Context, webhookDB *gorm.DB, webhookID string) {
 	var deliveries []database.Delivery
 	result := webhookDB.
 		Where("status = ?", database.DeliveryStatusPending).
@@ -569,6 +545,11 @@ func (e *Engine) processWebhookPendingDeliveries(ctx context.Context, webhookID
 		return
 	}
 
+	e.log.Info("recovering pending deliveries",
+		"webhook_id", webhookID,
+		"count", len(deliveries),
+	)
+
 	// Collect unique target IDs and load targets from the main DB
 	seen := make(map[string]bool)
 	targetIDs := make([]string, 0, len(deliveries))
@@ -590,8 +571,7 @@ func (e *Engine) processWebhookPendingDeliveries(ctx context.Context, webhookID
 		targetMap[t.ID] = t
 	}
 
-	// Fan out recovered deliveries in parallel — same as the normal
-	// delivery path, each task gets its own goroutine.
+	// Send recovered deliveries to the delivery channel for workers
 	for i := range deliveries {
 		select {
 		case <-ctx.Done():
@@ -607,10 +587,14 @@ func (e *Engine) processWebhookPendingDeliveries(ctx context.Context, webhookID
 			)
 			continue
 		}
-		deliveries[i].Target = target
 
-		// Build task from DB data for the recovery path
-		bodyStr := deliveries[i].Event.Body
+		// Build task from DB data
+		var bodyPtr *string
+		if len(deliveries[i].Event.Body) < MaxInlineBodySize {
+			bodyStr := deliveries[i].Event.Body
+			bodyPtr = &bodyStr
+		}
+
 		task := DeliveryTask{
 			DeliveryID:   deliveries[i].ID,
 			EventID:      deliveries[i].EventID,
@@ -623,21 +607,30 @@ func (e *Engine) processWebhookPendingDeliveries(ctx context.Context, webhookID
 			Method:       deliveries[i].Event.Method,
 			Headers:      deliveries[i].Event.Headers,
 			ContentType:  deliveries[i].Event.ContentType,
-			Body:         &bodyStr,
+			Body:         bodyPtr,
 			AttemptNum:   1,
 		}
 
-		d := deliveries[i] // copy for goroutine closure safety
-		go func() {
-			e.processDelivery(ctx, webhookDB, &d, &task)
-		}()
+		select {
+		case e.deliveryCh <- task:
+		default:
+			e.log.Warn("delivery channel full during recovery, remaining deliveries will be recovered on next restart",
+				"delivery_id", deliveries[i].ID,
+			)
+			return
+		}
 	}
 }
 
 // scheduleRetry creates a Go timer that fires after the given delay and
 // sends the full DeliveryTask to the engine's retry channel. The task
-// carries all data needed for the retry attempt, so when it fires, the
-// engine can deliver without reading event or target data from the DB.
+// carries all data needed for the retry attempt, so when it fires, a
+// worker can deliver without reading event or target data from the DB.
+//
+// If the retry channel is full when the timer fires, the timer is
+// dropped. The delivery remains in `retrying` status in the database
+// and will be picked up by the periodic retry sweep (DB-mediated
+// fallback path). No goroutines are blocked or re-armed.
 func (e *Engine) scheduleRetry(task DeliveryTask, delay time.Duration) {
 	e.log.Debug("scheduling delivery retry",
 		"webhook_id", task.WebhookID,
@@ -650,13 +643,189 @@ func (e *Engine) scheduleRetry(task DeliveryTask, delay time.Duration) {
 		select {
 		case e.retryCh <- task:
 		default:
-			e.log.Warn("retry channel full, delivery will be recovered on restart",
+			// Retry channel full — drop the timer. The delivery is
+			// already marked as `retrying` in the per-webhook DB, so
+			// the periodic retry sweep will pick it up. This is the
+			// DB-mediated fallback path: no blocked goroutines, no
+			// unbounded timer chains.
+			e.log.Warn("retry channel full, delivery will be recovered by periodic sweep",
 				"delivery_id", task.DeliveryID,
+				"webhook_id", task.WebhookID,
 			)
 		}
 	})
 }
 
+// retrySweep runs periodically to scan all per-webhook databases for
+// "orphaned" retrying deliveries — ones whose in-memory retry timer was
+// dropped because the retry channel was full. This is the DB-mediated
+// fallback path that ensures no retries are permanently lost even under
+// extreme backpressure.
+//
+// The sweep is also the same mechanism used on startup recovery, making
+// the system resilient to both channel overflow and unexpected restarts.
+func (e *Engine) retrySweep(ctx context.Context) {
+	defer e.wg.Done()
+	ticker := time.NewTicker(retrySweepInterval)
+	defer ticker.Stop()
+
+	for {
+		select {
+		case <-ctx.Done():
+			return
+		case <-ticker.C:
+			e.sweepOrphanedRetries(ctx)
+		}
+	}
+}
+
+// sweepOrphanedRetries scans all webhooks for retrying deliveries whose
+// backoff period has elapsed. For each eligible delivery, it builds a
+// DeliveryTask and sends it to the retry channel. If the channel is
+// still full, the delivery is skipped and will be retried on the next
+// sweep cycle.
+func (e *Engine) sweepOrphanedRetries(ctx context.Context) {
+	var webhookIDs []string
+	if err := e.database.DB().Model(&database.Webhook{}).Pluck("id", &webhookIDs).Error; err != nil {
+		e.log.Error("retry sweep: failed to query webhook IDs", "error", err)
+		return
+	}
+
+	for _, webhookID := range webhookIDs {
+		select {
+		case <-ctx.Done():
+			return
+		default:
+		}
+
+		if !e.dbManager.DBExists(webhookID) {
+			continue
+		}
+
+		e.sweepWebhookRetries(ctx, webhookID)
+	}
+}
+
+// sweepWebhookRetries scans a single webhook's database for retrying
+// deliveries whose backoff period has elapsed and sends them to the
+// retry channel.
+func (e *Engine) sweepWebhookRetries(ctx context.Context, webhookID string) {
+	webhookDB, err := e.dbManager.GetDB(webhookID)
+	if err != nil {
+		e.log.Error("retry sweep: failed to get webhook database",
+			"webhook_id", webhookID,
+			"error", err,
+		)
+		return
+	}
+
+	var retrying []database.Delivery
+	if err := webhookDB.Where("status = ?", database.DeliveryStatusRetrying).
+		Find(&retrying).Error; err != nil {
+		e.log.Error("retry sweep: failed to query retrying deliveries",
+			"webhook_id", webhookID,
+			"error", err,
+		)
+		return
+	}
+
+	for i := range retrying {
+		select {
+		case <-ctx.Done():
+			return
+		default:
+		}
+
+		d := &retrying[i]
+
+		// Count prior attempts to determine backoff
+		var resultCount int64
+		webhookDB.Model(&database.DeliveryResult{}).
+			Where("delivery_id = ?", d.ID).
+			Count(&resultCount)
+		attemptNum := int(resultCount)
+
+		// Check if the backoff period has elapsed since the last attempt.
+		// If it hasn't, this delivery likely has an active in-memory
+		// timer and is not orphaned — skip it.
+		var lastResult database.DeliveryResult
+		if err := webhookDB.Where("delivery_id = ?", d.ID).
+			Order("created_at DESC").
+			First(&lastResult).Error; err == nil {
+			shift := attemptNum - 1
+			if shift < 0 {
+				shift = 0
+			}
+			if shift > 30 {
+				shift = 30
+			}
+			backoff := time.Duration(1<<uint(shift)) * time.Second //nolint:gosec // bounded above
+			if time.Since(lastResult.CreatedAt) < backoff {
+				continue // Backoff hasn't elapsed; likely has an active timer
+			}
+		}
+		// If no result exists, the delivery was set to retrying but
+		// never actually attempted — process immediately.
+
+		// Load event for this delivery
+		var event database.Event
+		if err := webhookDB.First(&event, "id = ?", d.EventID).Error; err != nil {
+			e.log.Error("retry sweep: failed to load event",
+				"delivery_id", d.ID,
+				"event_id", d.EventID,
+				"error", err,
+			)
+			continue
+		}
+
+		// Load target from main DB
+		var target database.Target
+		if err := e.database.DB().First(&target, "id = ?", d.TargetID).Error; err != nil {
+			e.log.Error("retry sweep: failed to load target",
+				"delivery_id", d.ID,
+				"target_id", d.TargetID,
+				"error", err,
+			)
+			continue
+		}
+
+		// Build task from DB data
+		var bodyPtr *string
+		if len(event.Body) < MaxInlineBodySize {
+			bodyStr := event.Body
+			bodyPtr = &bodyStr
+		}
+
+		task := DeliveryTask{
+			DeliveryID:   d.ID,
+			EventID:      d.EventID,
+			WebhookID:    webhookID,
+			TargetID:     target.ID,
+			TargetName:   target.Name,
+			TargetType:   target.Type,
+			TargetConfig: target.Config,
+			MaxRetries:   target.MaxRetries,
+			Method:       event.Method,
+			Headers:      event.Headers,
+			ContentType:  event.ContentType,
+			Body:         bodyPtr,
+			AttemptNum:   attemptNum + 1,
+		}
+
+		// Try to send to retry channel; skip if still full
+		select {
+		case e.retryCh <- task:
+			e.log.Info("retry sweep: recovered orphaned retrying delivery",
+				"delivery_id", d.ID,
+				"webhook_id", webhookID,
+				"attempt", attemptNum+1,
+			)
+		default:
+			// Channel still full — will try again on the next sweep
+		}
+	}
+}
+
 func (e *Engine) processDelivery(ctx context.Context, webhookDB *gorm.DB, d *database.Delivery, task *DeliveryTask) {
 	switch d.Target.Type {
 	case database.TargetTypeHTTP: