diff --git a/app/jobs/webhook/cleanup_deliveries_job.rb b/app/jobs/webhook/cleanup_deliveries_job.rb
new file mode 100644
index 000000000..63f87ead5
--- /dev/null
+++ b/app/jobs/webhook/cleanup_deliveries_job.rb
@@ -0,0 +1,7 @@
+class Webhook::CleanupDeliveriesJob < ApplicationJob
+  def perform
+    ApplicationRecord.with_each_tenant do
+      Webhook::Delivery.cleanup
+    end
+  end
+end
diff --git a/app/models/webhook/delivery.rb b/app/models/webhook/delivery.rb
index 3624a2d0b..780d6772d 100644
--- a/app/models/webhook/delivery.rb
+++ b/app/models/webhook/delivery.rb
@@ -1,4 +1,5 @@
 class Webhook::Delivery < ApplicationRecord
+  STALE_TRESHOLD = 7.days
   USER_AGENT = "fizzy/1.0.0 Webhook"
   ENDPOINT_TIMEOUT = 7.seconds
   DNS_RESOLUTION_TIMEOUT = 2
@@ -18,9 +19,14 @@ class Webhook::Delivery < ApplicationRecord
   enum :state, %w[ pending in_progress completed errored ].index_by(&:itself), default: :pending
 
   scope :ordered, -> { order created_at: :desc, id: :desc }
+  scope :stale, -> { where(created_at: ...STALE_TRESHOLD.ago) }
 
   after_create_commit :deliver_later
 
+  def self.cleanup
+    stale.delete_all
+  end
+
   def deliver_later
     Webhook::DeliveryJob.perform_later(self)
   end
diff --git a/config/recurring.yml b/config/recurring.yml
index 45410859d..d6d68ae88 100644
--- a/config/recurring.yml
+++ b/config/recurring.yml
@@ -26,6 +26,9 @@ production: &production
   generate_weekly_highlights:
     command: "User.generate_all_weekly_highlights_later"
     schedule: every sunday at noon
+  cleanup_webhook_deliveries:
+    command: "Webhook::CleanupDeliveriesJob"
+    schedule: every 4 hours
 
 beta: *production
 staging: *production
diff --git a/test/models/webhook/delivery_test.rb b/test/models/webhook/delivery_test.rb
index b882559a7..8de7b6713 100644
--- a/test/models/webhook/delivery_test.rb
+++ b/test/models/webhook/delivery_test.rb
@@ -190,4 +190,17 @@ class Webhook::DeliveryTest < ActiveSupport::TestCase
     assert_requested request_stub
     assert delivery.succeeded?
   end
+
+  test "cleanup" do
+    webhook = webhooks(:active)
+    event = events(:layout_commented)
+
+    fresh_delivery = Webhook::Delivery.create!(webhook: webhook, event: event)
+    stale_delivery = Webhook::Delivery.create!(webhook: webhook, event: event, created_at: 8.days.ago)
+
+    Webhook::Delivery.cleanup
+
+    assert Webhook::Delivery.exists?(fresh_delivery.id)
+    assert_not Webhook::Delivery.exists?(stale_delivery.id)
+  end
 end