diff --git a/models/webhook/hooktask.go b/models/webhook/hooktask.go
index 246484aea96b2..92d9e97383337 100644
--- a/models/webhook/hooktask.go
+++ b/models/webhook/hooktask.go
@@ -233,14 +233,30 @@ func ReplayHookTask(ctx context.Context, hookID int64, uuid string) (*HookTask,
 	return newTask, db.Insert(ctx, newTask)
 }
 
-// FindUndeliveredHookTasks represents find the undelivered hook tasks
-func FindUndeliveredHookTasks(ctx context.Context) ([]*HookTask, error) {
-	tasks := make([]*HookTask, 0, 10)
+// FindUndeliveredHookTaskIDs will find the next 100 undelivered hook tasks with ID greater than the provided lowerID
+func FindUndeliveredHookTaskIDs(ctx context.Context, lowerID int64) ([]int64, error) {
+	const batchSize = 100
+
+	tasks := make([]int64, 0, batchSize)
 	return tasks, db.GetEngine(ctx).
+		Select("id").
+		Table(new(HookTask)).
 		Where("is_delivered=?", false).
+		And("id > ?", lowerID).
+		Asc("id").
+		Limit(batchSize).
 		Find(&tasks)
 }
 
+func MarkTaskDelivered(ctx context.Context, task *HookTask) (bool, error) {
+	count, err := db.GetEngine(ctx).ID(task.ID).Where("is_delivered = ?", false).Cols("is_delivered").Update(&HookTask{
+		ID:          task.ID,
+		IsDelivered: true,
+	})
+
+	return count != 0, err
+}
+
 // CleanupHookTaskTable deletes rows from hook_task as needed.
 func CleanupHookTaskTable(ctx context.Context, cleanupType HookTaskCleanupType, olderThan time.Duration, numberToKeep int) error {
 	log.Trace("Doing: CleanupHookTaskTable")
diff --git a/services/webhook/deliver.go b/services/webhook/deliver.go
index 85717e09783ed..07fdf18c83472 100644
--- a/services/webhook/deliver.go
+++ b/services/webhook/deliver.go
@@ -23,6 +23,7 @@ import (
 	"code.gitea.io/gitea/modules/graceful"
 	"code.gitea.io/gitea/modules/hostmatcher"
 	"code.gitea.io/gitea/modules/log"
+	"code.gitea.io/gitea/modules/process"
 	"code.gitea.io/gitea/modules/proxy"
 	"code.gitea.io/gitea/modules/queue"
 	"code.gitea.io/gitea/modules/setting"
@@ -43,7 +44,7 @@ func Deliver(ctx context.Context, t *webhook_model.HookTask) error {
 			return
 		}
 		// There was a panic whilst delivering a hook...
-		log.Error("PANIC whilst trying to deliver webhook[%d] to %s Panic: %v\nStacktrace: %s", t.ID, w.URL, err, log.Stack(2))
+		log.Error("PANIC whilst trying to deliver webhook task[%d] to webhook %s Panic: %v\nStacktrace: %s", t.ID, w.URL, err, log.Stack(2))
 	}()
 
 	t.IsDelivered = true
@@ -52,7 +53,7 @@ func Deliver(ctx context.Context, t *webhook_model.HookTask) error {
 
 	switch w.HTTPMethod {
 	case "":
-		log.Info("HTTP Method for webhook %d empty, setting to POST as default", t.ID)
+		log.Info("HTTP Method for webhook %s empty, setting to POST as default", w.URL)
 		fallthrough
 	case http.MethodPost:
 		switch w.ContentType {
@@ -78,14 +79,14 @@ func Deliver(ctx context.Context, t *webhook_model.HookTask) error {
 	case http.MethodGet:
 		u, err := url.Parse(w.URL)
 		if err != nil {
-			return err
+			return fmt.Errorf("unable to deliver webhook task[%d] as cannot parse webhook url %s: %w", t.ID, w.URL, err)
 		}
 		vals := u.Query()
 		vals["payload"] = []string{t.PayloadContent}
 		u.RawQuery = vals.Encode()
 		req, err = http.NewRequest("GET", u.String(), nil)
 		if err != nil {
-			return err
+			return fmt.Errorf("unable to deliver webhook task[%d] as unable to create HTTP request for webhook url %s: %w", t.ID, w.URL, err)
 		}
 	case http.MethodPut:
 		switch w.Type {
@@ -97,13 +98,13 @@ func Deliver(ctx context.Context, t *webhook_model.HookTask) error {
 			url := fmt.Sprintf("%s/%s", w.URL, url.PathEscape(txnID))
 			req, err = http.NewRequest("PUT", url, strings.NewReader(t.PayloadContent))
 			if err != nil {
-				return err
+				return fmt.Errorf("unable to deliver webhook task[%d] as cannot create matrix request for webhook url %s: %w", t.ID, w.URL, err)
 			}
 		default:
-			return fmt.Errorf("invalid http method for webhook: [%d] %v", t.ID, w.HTTPMethod)
+			return fmt.Errorf("invalid http method for webhook task[%d] in webhook %s: %v", t.ID, w.URL, w.HTTPMethod)
 		}
 	default:
-		return fmt.Errorf("invalid http method for webhook: [%d] %v", t.ID, w.HTTPMethod)
+		return fmt.Errorf("invalid http method for webhook task[%d] in webhook %s: %v", t.ID, w.URL, w.HTTPMethod)
 	}
 
 	var signatureSHA1 string
@@ -159,6 +160,20 @@ func Deliver(ctx context.Context, t *webhook_model.HookTask) error {
 		Headers: map[string]string{},
 	}
 
+	// OK We're now ready to attempt to deliver the task - we must double check that it
+	// has not been delivered in the meantime
+	updated, err := webhook_model.MarkTaskDelivered(ctx, t)
+	if err != nil {
+		log.Error("MarkTaskDelivered[%d]: %v", t.ID, err)
+		return fmt.Errorf("unable to mark task[%d] delivered in the db: %w", t.ID, err)
+	}
+	if !updated {
+		// This webhook task has already been attempted to be delivered or is in the process of being delivered
+		log.Trace("Webhook Task[%d] already delivered", t.ID)
+		return nil
+	}
+
+	// All code from this point will update the hook task
 	defer func() {
 		t.Delivered = time.Now().UnixNano()
 		if t.IsSucceed {
@@ -190,13 +205,14 @@ func Deliver(ctx context.Context, t *webhook_model.HookTask) error {
 	}
 
 	if !w.IsActive {
+		log.Trace("Webhook %s in Webhook Task[%d] is not active", w.URL, t.ID)
 		return nil
 	}
 
 	resp, err := webhookHTTPClient.Do(req.WithContext(ctx))
 	if err != nil {
 		t.ResponseInfo.Body = fmt.Sprintf("Delivery: %v", err)
-		return err
+		return fmt.Errorf("unable to deliver webhook task[%d] in %s due to error in http client: %w", t.ID, w.URL, err)
 	}
 	defer resp.Body.Close()
 
@@ -210,7 +226,7 @@ func Deliver(ctx context.Context, t *webhook_model.HookTask) error {
 	p, err := io.ReadAll(resp.Body)
 	if err != nil {
 		t.ResponseInfo.Body = fmt.Sprintf("read body: %s", err)
-		return err
+		return fmt.Errorf("unable to deliver webhook task[%d] in %s as unable to read response body: %w", t.ID, w.URL, err)
 	}
 	t.ResponseInfo.Body = string(p)
 	return nil
@@ -272,17 +288,37 @@ func Init() error {
 	}
 	go graceful.GetManager().RunWithShutdownFns(hookQueue.Run)
 
-	tasks, err := webhook_model.FindUndeliveredHookTasks(graceful.GetManager().HammerContext())
-	if err != nil {
-		log.Error("FindUndeliveredHookTasks failed: %v", err)
-		return err
-	}
+	go graceful.GetManager().RunWithShutdownContext(populateWebhookSendingQueue)
+
+	return nil
+}
+
+func populateWebhookSendingQueue(ctx context.Context) {
+	ctx, _, finished := process.GetManager().AddContext(ctx, "Webhook: Populate sending queue")
+	defer finished()
 
-	for _, task := range tasks {
-		if err := enqueueHookTask(task); err != nil {
-			log.Error("enqueueHookTask failed: %v", err)
+	lowerID := int64(0)
+	for {
+		taskIDs, err := webhook_model.FindUndeliveredHookTaskIDs(ctx, lowerID)
+		if err != nil {
+			log.Error("Unable to populate webhook queue as FindUndeliveredHookTaskIDs failed: %v", err)
+			return
+		}
+		if len(taskIDs) == 0 {
+			return
+		}
+		lowerID = taskIDs[len(taskIDs)-1]
+
+		for _, taskID := range taskIDs {
+			select {
+			case <-ctx.Done():
+				log.Warn("Shutdown before Webhook Sending queue finishing being populated")
+				return
+			default:
+			}
+			if err := enqueueHookTask(taskID); err != nil {
+				log.Error("Unable to push HookTask[%d] to the Webhook Sending queue: %v", taskID, err)
+			}
 		}
 	}
-
-	return nil
 }
diff --git a/services/webhook/deliver_test.go b/services/webhook/deliver_test.go
index 83ca7d61786d3..498cf7d159f02 100644
--- a/services/webhook/deliver_test.go
+++ b/services/webhook/deliver_test.go
@@ -16,6 +16,7 @@ import (
 	"code.gitea.io/gitea/models/unittest"
 	webhook_model "code.gitea.io/gitea/models/webhook"
 	"code.gitea.io/gitea/modules/setting"
+	api "code.gitea.io/gitea/modules/structs"
 
 	"github.com/stretchr/testify/assert"
 )
@@ -67,8 +68,15 @@ func TestWebhookDeliverAuthorizationHeader(t *testing.T) {
 	err := hook.SetHeaderAuthorization("Bearer s3cr3t-t0ken")
 	assert.NoError(t, err)
 	assert.NoError(t, webhook_model.CreateWebhook(db.DefaultContext, hook))
+	db.GetEngine(db.DefaultContext).NoAutoTime().DB().Logger.ShowSQL(true)
 
-	hookTask := &webhook_model.HookTask{HookID: hook.ID, EventType: webhook_model.HookEventPush}
+	hookTask := &webhook_model.HookTask{HookID: hook.ID, EventType: webhook_model.HookEventPush, Payloader: &api.PushPayload{}}
+
+	hookTask, err = webhook_model.CreateHookTask(db.DefaultContext, hookTask)
+	assert.NoError(t, err)
+	if !assert.NotNil(t, hookTask) {
+		return
+	}
 
 	assert.NoError(t, Deliver(context.Background(), hookTask))
 	select {
diff --git a/services/webhook/webhook.go b/services/webhook/webhook.go
index 1780022eb4b2f..5c9139b41f1c0 100644
--- a/services/webhook/webhook.go
+++ b/services/webhook/webhook.go
@@ -116,19 +116,26 @@ func handle(data ...queue.Data) []queue.Data {
 	for _, taskID := range data {
 		task, err := webhook_model.GetHookTaskByID(ctx, taskID.(int64))
 		if err != nil {
-			log.Error("GetHookTaskByID failed: %v", err)
-		} else {
-			if err := Deliver(ctx, task); err != nil {
-				log.Error("webhook.Deliver failed: %v", err)
-			}
+			log.Error("GetHookTaskByID[%d] failed: %v", taskID.(int64), err)
+			continue
+		}
+
+		if task.IsDelivered {
+			// Already delivered in the meantime
+			log.Trace("Task[%d] has already been delivered", task.ID)
+			continue
+		}
+
+		if err := Deliver(ctx, task); err != nil {
+			log.Error("Unable to deliver webhook task[%d]: %v", task.ID, err)
 		}
 	}
 
 	return nil
 }
 
-func enqueueHookTask(task *webhook_model.HookTask) error {
-	err := hookQueue.PushFunc(task.ID, nil)
+func enqueueHookTask(taskID int64) error {
+	err := hookQueue.Push(taskID)
 	if err != nil && err != queue.ErrAlreadyInQueue {
 		return err
 	}
@@ -205,7 +212,7 @@ func PrepareWebhook(ctx context.Context, w *webhook_model.Webhook, event webhook
 		return fmt.Errorf("CreateHookTask: %w", err)
 	}
 
-	return enqueueHookTask(task)
+	return enqueueHookTask(task.ID)
 }
 
 // PrepareWebhooks adds new webhooks to task queue for given payload.
@@ -265,5 +272,5 @@ func ReplayHookTask(ctx context.Context, w *webhook_model.Webhook, uuid string)
 		return err
 	}
 
-	return enqueueHookTask(task)
+	return enqueueHookTask(task.ID)
 }