diff --git a/Gemfile b/Gemfile
index 3d8e485e56e..608c8703629 100644
--- a/Gemfile
+++ b/Gemfile
@@ -136,6 +136,9 @@ gem 'view_component_reflex', '3.1.14.pre9'
 
 gem 'mini_portile2', '~> 2.8'
 
+gem "faraday"
+gem "private_address_check"
+
 group :production, :staging do
   gem 'ddtrace'
   gem 'rack-timeout'
diff --git a/Gemfile.lock b/Gemfile.lock
index 9a1b5b2bb91..caa5a208cb5 100644
--- a/Gemfile.lock
+++ b/Gemfile.lock
@@ -474,6 +474,7 @@ GEM
       ttfunk
     pg (1.2.3)
     power_assert (2.0.2)
+    private_address_check (0.5.0)
     pry (0.13.1)
       coderay (~> 1.1)
       method_source (~> 1.0)
@@ -801,6 +802,7 @@ DEPENDENCIES
   digest
   dotenv-rails
   factory_bot_rails (= 6.2.0)
+  faraday
   ffaker
   flipper
   flipper-active_record
@@ -843,6 +845,7 @@ DEPENDENCIES
   paypal-sdk-merchant (= 1.117.2)
   pdf-reader
   pg (~> 1.2.3)
+  private_address_check
   pry (~> 0.13.0)
   puma
   rack-mini-profiler (< 3.0.0)
diff --git a/app/controllers/webhook_endpoints_controller.rb b/app/controllers/webhook_endpoints_controller.rb
new file mode 100644
index 00000000000..c9493f42bb4
--- /dev/null
+++ b/app/controllers/webhook_endpoints_controller.rb
@@ -0,0 +1,47 @@
+# frozen_string_literal: true
+
+class WebhookEndpointsController < ::BaseController
+  before_action :load_resource, only: :destroy
+
+  def create
+    webhook_endpoint = spree_current_user.webhook_endpoints.new(webhook_endpoint_params)
+
+    if webhook_endpoint.save
+      flash[:success] = t('.success')
+    else
+      flash[:error] = t('.error')
+    end
+
+    redirect_to redirect_path
+  end
+
+  def destroy
+    if @webhook_endpoint.destroy
+      flash[:success] = t('.success')
+    else
+      flash[:error] = t('.error')
+    end
+
+    redirect_to redirect_path
+  end
+
+  def load_resource
+    @webhook_endpoint = spree_current_user.webhook_endpoints.find(params[:id])
+  end
+
+  def webhook_endpoint_params
+    params.require(:webhook_endpoint).permit(:url)
+  end
+
+  def redirect_path
+    if request.referer.blank? || request.referer.include?(spree.account_path)
+      developer_settings_path
+    else
+      request.referer
+    end
+  end
+
+  def developer_settings_path
+    "#{spree.account_path}#/developer_settings"
+  end
+end
diff --git a/app/jobs/order_cycle_opened_job.rb b/app/jobs/order_cycle_opened_job.rb
new file mode 100644
index 00000000000..9d84027fe30
--- /dev/null
+++ b/app/jobs/order_cycle_opened_job.rb
@@ -0,0 +1,27 @@
+# frozen_string_literal: true
+
+# Trigger jobs for any order cycles that recently opened
+class OrderCycleOpenedJob < ApplicationJob
+  def perform
+    ActiveRecord::Base.transaction do
+      recently_opened_order_cycles.find_each do |order_cycle|
+        OrderCycleWebhookService.create_webhook_job(order_cycle, 'order_cycle.opened')
+      end
+      mark_as_opened(recently_opened_order_cycles)
+    end
+  end
+
+  private
+
+  def recently_opened_order_cycles
+    @recently_opened_order_cycles ||= OrderCycle
+      .where(opened_at: nil)
+      .where(orders_open_at: 1.hour.ago..Time.zone.now)
+      .lock.order(:id)
+  end
+
+  def mark_as_opened(order_cycles)
+    now = Time.zone.now
+    order_cycles.update_all(opened_at: now, updated_at: now)
+  end
+end
diff --git a/app/jobs/webhook_delivery_job.rb b/app/jobs/webhook_delivery_job.rb
new file mode 100644
index 00000000000..7eb0a44b832
--- /dev/null
+++ b/app/jobs/webhook_delivery_job.rb
@@ -0,0 +1,50 @@
+# frozen_string_literal: true
+
+require "faraday"
+require "private_address_check"
+require "private_address_check/tcpsocket_ext"
+
+# Deliver a webhook payload
+# As a delayed job, it can run asynchronously and handle retries.
+class WebhookDeliveryJob < ApplicationJob
+  # General failed request error that we're going to use to signal
+  # the job runner to retry our webhook worker.
+  class FailedWebhookRequestError < StandardError; end
+
+  queue_as :default
+
+  def perform(url, event, payload)
+    body = {
+      id: job_id,
+      at: Time.zone.now.to_s,
+      event: event,
+      data: payload,
+    }
+
+    # Request user-submitted url, preventing any private connections being made
+    # (SSRF).
+    # This method may allow the socket to open, but is necessary in order to
+    # protect from TOC/TOU.
+    # Note that private_address_check provides some methods for pre-validating,
+    # but they're not as comprehensive and so unnecessary here. Simply
+    # momentarily opening sockets probably can't cause DoS or other damage.
+    PrivateAddressCheck.only_public_connections do
+      notify_endpoint(url, body)
+    end
+  end
+
+  def notify_endpoint(url, body)
+    connection = Faraday.new(
+      request: { timeout: 30 },
+      headers: {
+        'User-Agent' => 'openfoodnetwork_webhook/1.0',
+        'Content-Type' => 'application/json',
+      }
+    )
+    response = connection.post(url, body.to_json)
+
+    # Raise a failed request error and let job runner handle retrying.
+    # In theory, only 5xx errors should be retried, but who knows.
+    raise FailedWebhookRequestError, response.status.to_s unless response.success?
+  end
+end
diff --git a/app/models/order_cycle.rb b/app/models/order_cycle.rb
index ce1846cf540..4eb3bc90608 100644
--- a/app/models/order_cycle.rb
+++ b/app/models/order_cycle.rb
@@ -34,6 +34,7 @@ class OrderCycle < ApplicationRecord
 
   attr_accessor :incoming_exchanges, :outgoing_exchanges
 
+  before_update :reset_opened_at, if: :will_save_change_to_orders_open_at?
   before_update :reset_processed_at, if: :will_save_change_to_orders_close_at?
   after_save :sync_subscriptions, if: :opening?
 
@@ -333,6 +334,14 @@ def orders_close_at_after_orders_open_at?
     errors.add(:orders_close_at, :after_orders_open_at)
   end
 
+  def reset_opened_at
+    # Reset only if order cycle is opening again at a later date
+    return unless orders_open_at.present? && orders_open_at_was.present?
+    return unless orders_open_at > orders_open_at_was
+
+    self.opened_at = nil
+  end
+
   def reset_processed_at
     return unless orders_close_at.present? && orders_close_at_was.present?
     return unless orders_close_at > orders_close_at_was
diff --git a/app/models/spree/user.rb b/app/models/spree/user.rb
index e95df0fcfd5..879825e9baf 100644
--- a/app/models/spree/user.rb
+++ b/app/models/spree/user.rb
@@ -38,7 +38,10 @@ class User < ApplicationRecord
     has_many :customers
     has_many :credit_cards
     has_many :report_rendering_options, class_name: "::ReportRenderingOptions", dependent: :destroy
+    has_many :webhook_endpoints, dependent: :destroy
+
     accepts_nested_attributes_for :enterprise_roles, allow_destroy: true
+    accepts_nested_attributes_for :webhook_endpoints
 
     accepts_nested_attributes_for :bill_address
     accepts_nested_attributes_for :ship_address
diff --git a/app/models/webhook_endpoint.rb b/app/models/webhook_endpoint.rb
new file mode 100644
index 00000000000..8626e11b934
--- /dev/null
+++ b/app/models/webhook_endpoint.rb
@@ -0,0 +1,6 @@
+# frozen_string_literal: true
+
+# Records a webhook url to send notifications to
+class WebhookEndpoint < ApplicationRecord
+  validates :url, presence: true
+end
diff --git a/app/services/order_cycle_webhook_service.rb b/app/services/order_cycle_webhook_service.rb
new file mode 100644
index 00000000000..f2d4df152ae
--- /dev/null
+++ b/app/services/order_cycle_webhook_service.rb
@@ -0,0 +1,21 @@
+# frozen_string_literal: true
+
+# Create a webhook payload for an order cycle event.
+# The payload will be delivered asynchronously.
+class OrderCycleWebhookService
+  def self.create_webhook_job(order_cycle, event)
+    webhook_payload = order_cycle
+      .slice(:id, :name, :orders_open_at, :orders_close_at, :coordinator_id)
+      .merge(coordinator_name: order_cycle.coordinator.name)
+
+    # Endpoints for coordinator owner
+    webhook_endpoints = order_cycle.coordinator.owner.webhook_endpoints
+
+    # Plus unique endpoints for distributor owners (ignore duplicates)
+    webhook_endpoints |= order_cycle.distributors.map(&:owner).flat_map(&:webhook_endpoints)
+
+    webhook_endpoints.each do |endpoint|
+      WebhookDeliveryJob.perform_later(endpoint.url, event, webhook_payload)
+    end
+  end
+end
diff --git a/app/services/permitted_attributes/user.rb b/app/services/permitted_attributes/user.rb
index 0b511bab218..4bb29bbcc48 100644
--- a/app/services/permitted_attributes/user.rb
+++ b/app/services/permitted_attributes/user.rb
@@ -15,7 +15,10 @@ def call(extra_permitted_attributes = [])
     private
 
     def permitted_attributes
-      [:email, :password, :password_confirmation, :disabled]
+      [
+        :email, :password, :password_confirmation, :disabled,
+        { webhook_endpoints_attributes: [:id, :url] },
+      ]
     end
   end
 end
diff --git a/app/views/spree/users/_developer_settings.html.haml b/app/views/spree/users/_developer_settings.html.haml
index b98ed527d51..fe6f6c5d046 100644
--- a/app/views/spree/users/_developer_settings.html.haml
+++ b/app/views/spree/users/_developer_settings.html.haml
@@ -1,3 +1,4 @@
 %script{ type: "text/ng-template", id: "account/developer_settings.html" }
   %h3= t('.title')
   = render partial: 'api_keys'
+  = render partial: 'webhook_endpoints'
diff --git a/app/views/spree/users/_webhook_endpoints.html.haml b/app/views/spree/users/_webhook_endpoints.html.haml
new file mode 100644
index 00000000000..8bd60e2f8b4
--- /dev/null
+++ b/app/views/spree/users/_webhook_endpoints.html.haml
@@ -0,0 +1,33 @@
+%section{ id: "webhook_endpoints" }
+  %hr
+  %h3= t('.title')
+  %p= t('.description')
+
+  %table{width: "100%"}
+    %thead
+      %tr
+        %th= t('.event_type.header')
+        %th= t('.url.header')
+        %th.actions
+    %tbody
+      -# Existing endpoints
+      - @user.webhook_endpoints.each do |webhook_endpoint|
+        %tr
+          %td= t('.event_types.order_cycle_opened') # For now, we only support one type.
+          %td= webhook_endpoint.url
+          %td.actions
+            - if webhook_endpoint.persisted?
+              = button_to account_webhook_endpoint_path(webhook_endpoint), method: :delete,
+                class: "tiny alert no-margin",
+                data: { confirm: I18n.t(:are_you_sure)} do
+                = I18n.t(:delete)
+
+      -# Create new
+      - if @user.webhook_endpoints.empty? # Only one allowed for now.
+        %tr
+          %td= t('.event_types.order_cycle_opened') # For now, we only support one type.
+          %td
+            = form_for(@user.webhook_endpoints.build, url: account_webhook_endpoints_path, id: 'new_webhook_endpoint') do |f|
+              = f.url_field :url, placeholder: t('.url.create_placeholder'), required: true, size: 64
+          %td.actions
+            = button_tag t(:create), class: 'button primary tiny no-margin', form: 'new_webhook_endpoint'
diff --git a/config/locales/en.yml b/config/locales/en.yml
index 761411574e9..81e2ace90de 100644
--- a/config/locales/en.yml
+++ b/config/locales/en.yml
@@ -3562,6 +3562,14 @@ See the %{link} to find out more about %{sitename}'s features and to start using
   previous: "Previous"
   last: "Last"
 
+  webhook_endpoints:
+    create:
+      success: Webhook endpoint successfully created
+      error: Webhook endpoint failed to create
+    destroy:
+      success: Webhook endpoint successfully deleted
+      error: Webhook endpoint failed to delete
+
   spree:
     order_updated: "Order Updated"
     add_country: "Add country"
@@ -4357,6 +4365,16 @@ See the %{link} to find out more about %{sitename}'s features and to start using
       api_keys:
         regenerate_key: "Regenerate Key"
         title: API key
+      webhook_endpoints:
+        title: Webhook Endpoints
+        description: Events in the system may trigger webhooks to external systems.
+        event_types:
+          order_cycle_opened: Order Cycle Opened
+        event_type:
+          header: Event type
+        url:
+          header: Endpoint URL
+          create_placeholder: Enter the URL of the remote webhook endpoint
       developer_settings:
         title: Developer Settings
       form:
diff --git a/config/routes/spree.rb b/config/routes/spree.rb
index c658cbdc214..9844b800e50 100644
--- a/config/routes/spree.rb
+++ b/config/routes/spree.rb
@@ -32,7 +32,9 @@
     put '/password/change' => 'user_passwords#update', :as => :update_password
   end
 
-  resource :account, :controller => 'users'
+  resource :account, :controller => 'users' do
+    resources :webhook_endpoints, only: [:create, :destroy], controller: '/webhook_endpoints'
+  end
 
   match '/admin/orders/bulk_management' => 'admin/orders#bulk_management', :as => "admin_bulk_order_management", via: :get
   match '/admin/payment_methods/show_provider_preferences' => 'admin/payment_methods#show_provider_preferences', :via => :get
diff --git a/config/sidekiq.yml b/config/sidekiq.yml
index c58aca0333c..eab2b061dbc 100644
--- a/config/sidekiq.yml
+++ b/config/sidekiq.yml
@@ -15,5 +15,7 @@
       every: "5m"
     SubscriptionConfirmJob:
       every: "5m"
+    OrderCycleOpenedJob:
+      every: "5m"
     OrderCycleClosingJob:
       every: "5m"
diff --git a/db/migrate/20220919063831_add_opened_at_to_order_cycle.rb b/db/migrate/20220919063831_add_opened_at_to_order_cycle.rb
new file mode 100644
index 00000000000..802ce193557
--- /dev/null
+++ b/db/migrate/20220919063831_add_opened_at_to_order_cycle.rb
@@ -0,0 +1,7 @@
+# frozen_string_literal: true
+
+class AddOpenedAtToOrderCycle < ActiveRecord::Migration[6.1]
+  def change
+    add_column :order_cycles, :opened_at, :timestamp
+  end
+end
diff --git a/db/migrate/20221028051650_create_webhook_endpoints.rb b/db/migrate/20221028051650_create_webhook_endpoints.rb
new file mode 100644
index 00000000000..034d1141d2f
--- /dev/null
+++ b/db/migrate/20221028051650_create_webhook_endpoints.rb
@@ -0,0 +1,11 @@
+# frozen_string_literal: true
+
+class CreateWebhookEndpoints < ActiveRecord::Migration[6.1]
+  def change
+    create_table :webhook_endpoints do |t|
+      t.string :url, null: false
+
+      t.timestamps null: false
+    end
+  end
+end
diff --git a/db/migrate/20221028053214_add_spree_user_reference_to_webhook_endpoint.rb b/db/migrate/20221028053214_add_spree_user_reference_to_webhook_endpoint.rb
new file mode 100644
index 00000000000..462e978b9c1
--- /dev/null
+++ b/db/migrate/20221028053214_add_spree_user_reference_to_webhook_endpoint.rb
@@ -0,0 +1,9 @@
+# frozen_string_literal: true
+
+class AddSpreeUserReferenceToWebhookEndpoint < ActiveRecord::Migration[6.1]
+  def change
+    add_column :webhook_endpoints, :user_id, :bigint, default: 0, null: false
+    add_index :webhook_endpoints, :user_id
+    add_foreign_key :webhook_endpoints, :spree_users, column: :user_id
+  end
+end
diff --git a/db/schema.rb b/db/schema.rb
index 77975612f5d..8e6da5fe19f 100644
--- a/db/schema.rb
+++ b/db/schema.rb
@@ -310,6 +310,7 @@
     t.datetime "processed_at"
     t.boolean "automatic_notifications", default: false
     t.boolean "mails_sent", default: false
+    t.datetime "opened_at"
   end
 
   create_table "order_cycles_distributor_payment_methods", id: false, force: :cascade do |t|
@@ -1189,6 +1190,14 @@
     t.index ["item_type", "item_id"], name: "index_versions_on_item_type_and_item_id"
   end
 
+  create_table "webhook_endpoints", force: :cascade do |t|
+    t.string "url", null: false
+    t.datetime "created_at", precision: 6, null: false
+    t.datetime "updated_at", precision: 6, null: false
+    t.bigint "user_id", default: 0, null: false
+    t.index ["user_id"], name: "index_webhook_endpoints_on_user_id"
+  end
+
   add_foreign_key "active_storage_attachments", "active_storage_blobs", column: "blob_id"
   add_foreign_key "active_storage_variant_records", "active_storage_blobs", column: "blob_id"
   add_foreign_key "adjustment_metadata", "enterprises", name: "adjustment_metadata_enterprise_id_fk"
@@ -1293,4 +1302,5 @@
   add_foreign_key "subscriptions", "spree_shipping_methods", column: "shipping_method_id", name: "subscriptions_shipping_method_id_fk"
   add_foreign_key "variant_overrides", "enterprises", column: "hub_id", name: "variant_overrides_hub_id_fk"
   add_foreign_key "variant_overrides", "spree_variants", column: "variant_id", name: "variant_overrides_variant_id_fk"
+  add_foreign_key "webhook_endpoints", "spree_users", column: "user_id"
 end
diff --git a/spec/controllers/webhook_endpoints_controller_spec.rb b/spec/controllers/webhook_endpoints_controller_spec.rb
new file mode 100644
index 00000000000..c36720edb8f
--- /dev/null
+++ b/spec/controllers/webhook_endpoints_controller_spec.rb
@@ -0,0 +1,67 @@
+# frozen_string_literal: false
+
+require 'spec_helper'
+require 'open_food_network/order_cycle_permissions'
+
+describe WebhookEndpointsController, type: :controller do
+  let(:user) { create(:admin_user) }
+
+  before { allow(controller).to receive(:spree_current_user) { user } }
+
+  describe "#create" do
+    it "creates a webhook_endpoint" do
+      expect {
+        spree_post :create, { url: "https://url" }
+      }.to change {
+        user.webhook_endpoints.count
+      }.by(1)
+
+      expect(flash[:success]).to be_present
+      expect(flash[:error]).to be_blank
+      expect(user.webhook_endpoints.first.url).to eq "https://url"
+    end
+
+    it "shows error if parameters not specified" do
+      expect {
+        spree_post :create, { url: "" }
+      }.to_not change {
+        user.webhook_endpoints.count
+      }
+
+      expect(flash[:success]).to be_blank
+      expect(flash[:error]).to be_present
+    end
+
+    it "redirects back to referrer" do
+      spree_post :create, { url: "https://url" }
+
+      expect(response).to redirect_to "/account#/developer_settings"
+    end
+  end
+
+  describe "#destroy" do
+    let!(:webhook_endpoint) { user.webhook_endpoints.create(url: "https://url") }
+
+    it "destroys a webhook_endpoint" do
+      webhook_endpoint2 = user.webhook_endpoints.create!(url: "https://url2")
+
+      expect {
+        spree_delete :destroy, { id: webhook_endpoint.id }
+      }.to change {
+        user.webhook_endpoints.count
+      }.by(-1)
+
+      expect(flash[:success]).to be_present
+      expect(flash[:error]).to be_blank
+
+      expect{ webhook_endpoint.reload }.to raise_error(ActiveRecord::RecordNotFound)
+      expect(webhook_endpoint2.reload).to be_present
+    end
+
+    it "redirects back to developer settings tab" do
+      spree_delete :destroy, id: webhook_endpoint.id
+
+      expect(response).to redirect_to "/account#/developer_settings"
+    end
+  end
+end
diff --git a/spec/jobs/order_cycle_opened_job_spec.rb b/spec/jobs/order_cycle_opened_job_spec.rb
new file mode 100644
index 00000000000..142cc01b0e8
--- /dev/null
+++ b/spec/jobs/order_cycle_opened_job_spec.rb
@@ -0,0 +1,62 @@
+# frozen_string_literal: true
+
+require 'spec_helper'
+
+describe OrderCycleOpenedJob do
+  let(:oc_opened_before) {
+    create(:order_cycle, orders_open_at: Time.zone.now - 1.hour)
+  }
+  let(:oc_opened_now) {
+    create(:order_cycle, orders_open_at: Time.zone.now)
+  }
+  let(:oc_opening_soon) {
+    create(:order_cycle, orders_open_at: Time.zone.now + 1.minute)
+  }
+
+  it "enqueues jobs for recently opened order cycles only" do
+    expect(OrderCycleWebhookService)
+      .to receive(:create_webhook_job).with(oc_opened_now, 'order_cycle.opened')
+
+    expect(OrderCycleWebhookService)
+      .to_not receive(:create_webhook_job).with(oc_opened_before, 'order_cycle.opened')
+
+    expect(OrderCycleWebhookService)
+      .to_not receive(:create_webhook_job).with(oc_opening_soon, 'order_cycle.opened')
+
+    OrderCycleOpenedJob.perform_now
+  end
+
+  describe "concurrency", concurrency: true do
+    let(:breakpoint) { Mutex.new }
+
+    it "doesn't place duplicate job when run concurrently" do
+      oc_opened_now
+
+      # Pause jobs when placing new job:
+      breakpoint.lock
+      allow(OrderCycleOpenedJob).to(
+        receive(:new).and_wrap_original do |method, *args|
+          breakpoint.synchronize {}
+          method.call(*args)
+        end
+      )
+
+      expect(OrderCycleWebhookService)
+        .to receive(:create_webhook_job).with(oc_opened_now, 'order_cycle.opened').once
+
+      # Start two jobs in parallel:
+      threads = [
+        Thread.new { OrderCycleOpenedJob.perform_now },
+        Thread.new { OrderCycleOpenedJob.perform_now },
+      ]
+
+      # Wait for both to jobs to pause.
+      # This can reveal a race condition.
+      sleep 0.1
+
+      # Resume and complete both jobs:
+      breakpoint.unlock
+      threads.each(&:join)
+    end
+  end
+end
diff --git a/spec/jobs/webhook_delivery_job_spec.rb b/spec/jobs/webhook_delivery_job_spec.rb
new file mode 100644
index 00000000000..7add4ca4e1e
--- /dev/null
+++ b/spec/jobs/webhook_delivery_job_spec.rb
@@ -0,0 +1,87 @@
+# frozen_string_literal: true
+
+require 'spec_helper'
+
+describe WebhookDeliveryJob do
+  subject { WebhookDeliveryJob.new(url, event, data) }
+  let(:url) { 'https://test/endpoint' }
+  let(:event) { 'order_cycle.opened' }
+  let(:data) {
+    {
+      order_cycle_id: 123, name: "Order cycle 1", open_at: 1.minute.ago.to_s, tags: ["tag1", "tag2"]
+    }
+  }
+
+  before do
+    stub_request(:post, url)
+  end
+
+  it "sends a request to specified url" do
+    subject.perform_now
+    expect(a_request(:post, url)).to have_been_made.once
+  end
+
+  it "delivers a payload" do
+    Timecop.freeze do
+      expected_body = {
+        id: /.+/,
+        at: Time.zone.now.to_s,
+        event: event,
+        data: data,
+      }
+
+      subject.perform_now
+      expect(a_request(:post, url).with(body: expected_body)).
+        to have_been_made.once
+    end
+  end
+
+  # Ensure responses from a local network aren't allowed, to prevent a user
+  # seeing a private response or initiating an unauthorised action (SSRF).
+  # Currently, we're not doing anything with responses. When we do, we should
+  # update this to confirm the response isn't exposed.
+  describe "server side request forgery" do
+    describe "private addresses" do
+      private_addresses = [
+        "http://127.0.0.1/all_the_secrets",
+        "http://localhost/all_the_secrets",
+      ]
+
+      private_addresses.each do |url|
+        it "rejects private address #{url}" do
+          # Github Actions doesn't allow local connections.
+          pending if ENV["CI"]
+          expect {
+            WebhookDeliveryJob.perform_now(url, event, data)
+          }.to raise_error(PrivateAddressCheck::PrivateConnectionAttemptedError)
+        end
+      end
+    end
+
+    describe "redirects" do
+      it "doesn't follow a redirect" do
+        other_url = 'http://localhost/all_the_secrets'
+
+        stub_request(:post, url).
+          to_return(status: 302, headers: { 'Location' => other_url })
+        stub_request(:any, other_url)
+
+        expect {
+          subject.perform_now
+        }.to raise_error(StandardError, "302")
+
+        expect(a_request(:any, other_url)).not_to have_been_made
+      end
+    end
+  end
+
+  # Exceptions are considered a job failure, which the job runner
+  # (Sidekiq) and/or ActiveJob will handle and retry later.
+  describe "failure" do
+    it "raises error on server error" do
+      stub_request(:post, url).to_return(status: [500, "Internal Server Error"])
+
+      expect{ subject.perform_now }.to raise_error(StandardError, "500")
+    end
+  end
+end
diff --git a/spec/models/order_cycle_spec.rb b/spec/models/order_cycle_spec.rb
index 818b900e196..fe80bd3d789 100644
--- a/spec/models/order_cycle_spec.rb
+++ b/spec/models/order_cycle_spec.rb
@@ -551,6 +551,27 @@
     end
   end
 
+  describe "opened_at " do
+    let!(:oc) {
+      create(:simple_order_cycle, orders_open_at: 2.days.ago, orders_close_at: 1.day.ago, opened_at: 1.week.ago)
+    }
+
+    it "reset opened_at if open date change in future" do
+      expect{ oc.update!(orders_open_at: 1.week.from_now, orders_close_at: 2.weeks.from_now) }
+        .to change { oc.opened_at }.to be_nil
+    end
+
+    it "it does not reset opened_at if open date is changed to be earlier" do
+      expect{ oc.update!(orders_open_at: 3.days.ago) }
+        .to_not change { oc.opened_at }
+    end
+
+    it "it does not reset opened_at if open date does not change" do
+      expect{ oc.update!(orders_close_at: 1.day.from_now) }
+        .to_not change { oc.opened_at }
+    end
+  end
+
   describe "processed_at " do
     let!(:oc) {
       create(:simple_order_cycle, orders_open_at: 1.week.ago, orders_close_at: 1.day.ago, processed_at: 1.hour.ago)
@@ -562,13 +583,13 @@
       expect(oc.processed_at).to be_nil
     end
 
-    it "it does not reset processed_at if close date change in the past" do
+    it "it does not reset processed_at if close date is changed to be earlier" do
       expect(oc.processed_at).to_not be_nil
       oc.update!(orders_close_at: 2.days.ago)
       expect(oc.processed_at).to_not be_nil
     end
 
-    it "it does not reset processed_at if close date do not change" do
+    it "it does not reset processed_at if close date does not change" do
       expect(oc.processed_at).to_not be_nil
       oc.update!(orders_open_at: 2.weeks.ago)
       expect(oc.processed_at).to_not be_nil
diff --git a/spec/models/spree/user_spec.rb b/spec/models/spree/user_spec.rb
index a99a18941dc..9dac88ad760 100644
--- a/spec/models/spree/user_spec.rb
+++ b/spec/models/spree/user_spec.rb
@@ -7,6 +7,7 @@
 
   describe "associations" do
     it { is_expected.to have_many(:owned_enterprises) }
+    it { is_expected.to have_many(:webhook_endpoints).dependent(:destroy) }
 
     describe "addresses" do
       let(:user) { create(:user, bill_address: create(:address)) }
diff --git a/spec/models/webhook_endpoint_spec.rb b/spec/models/webhook_endpoint_spec.rb
new file mode 100644
index 00000000000..5f1d630f099
--- /dev/null
+++ b/spec/models/webhook_endpoint_spec.rb
@@ -0,0 +1,9 @@
+# frozen_string_literal: true
+
+require 'spec_helper'
+
+describe WebhookEndpoint, type: :model do
+  describe "validations" do
+    it { is_expected.to validate_presence_of(:url) }
+  end
+end
diff --git a/spec/services/order_cycle_webhook_service_spec.rb b/spec/services/order_cycle_webhook_service_spec.rb
new file mode 100644
index 00000000000..e5c1285e2be
--- /dev/null
+++ b/spec/services/order_cycle_webhook_service_spec.rb
@@ -0,0 +1,143 @@
+# frozen_string_literal: true
+
+require 'spec_helper'
+
+describe OrderCycleWebhookService do
+  let(:order_cycle) {
+    create(
+      :simple_order_cycle,
+      name: "Order cycle 1",
+      orders_open_at: "2022-09-19 09:00:00".to_time,
+      orders_close_at: "2022-09-19 17:00:00".to_time,
+      coordinator: coordinator,
+    )
+  }
+  let(:coordinator) { create :distributor_enterprise, name: "Starship Enterprise" }
+
+  describe "creating payloads" do
+    it "doesn't create webhook payload for enterprise users" do
+      # The co-ordinating enterprise has a non-owner user with an endpoint.
+      # They shouldn't receive a notification.
+      coordinator_user = create(:user, enterprises: [coordinator])
+      coordinator_user.webhook_endpoints.create!(url: "http://coordinator_user_url")
+
+      expect{ OrderCycleWebhookService.create_webhook_job(order_cycle, "order_cycle.opened") }
+        .to_not enqueue_job(WebhookDeliveryJob).with("http://coordinator_user_url", any_args)
+    end
+
+    context "coordinator owner has endpoint configured" do
+      before do
+        coordinator.owner.webhook_endpoints.create! url: "http://coordinator_owner_url"
+      end
+
+      it "creates webhook payload for order cycle coordinator" do
+        expect{ OrderCycleWebhookService.create_webhook_job(order_cycle, "order_cycle.opened") }
+          .to enqueue_job(WebhookDeliveryJob).with("http://coordinator_owner_url", any_args)
+      end
+
+      it "creates webhook payload with details for the specified order cycle only" do
+        # The coordinating enterprise has another OC. It should be ignored.
+        order_cycle.dup.save
+
+        data = {
+          id: order_cycle.id,
+          name: "Order cycle 1",
+          orders_open_at: "2022-09-19 09:00:00".to_time,
+          orders_close_at: "2022-09-19 17:00:00".to_time,
+          coordinator_id: coordinator.id,
+          coordinator_name: "Starship Enterprise",
+        }
+
+        expect{ OrderCycleWebhookService.create_webhook_job(order_cycle, "order_cycle.opened") }
+          .to enqueue_job(WebhookDeliveryJob).exactly(1).times
+          .with("http://coordinator_owner_url", "order_cycle.opened", hash_including(data))
+      end
+    end
+
+    context "coordinator owner doesn't have endpoint configured" do
+      it "doesn't create webhook payload" do
+        expect{ OrderCycleWebhookService.create_webhook_job(order_cycle, "order_cycle.opened") }
+          .not_to enqueue_job(WebhookDeliveryJob)
+      end
+    end
+
+    describe "distributors" do
+      context "multiple distributors have owners with endpoint configured" do
+        let(:order_cycle) {
+          create(
+            :simple_order_cycle,
+            coordinator: coordinator,
+            distributors: two_distributors,
+          )
+        }
+        let(:two_distributors) {
+          (1..2).map do |i|
+            user = create(:user)
+            user.webhook_endpoints.create!(url: "http://distributor#{i}_owner_url")
+            create(:distributor_enterprise, owner: user)
+          end
+        }
+
+        it "creates webhook payload for each order cycle distributor" do
+          data = {
+            coordinator_id: order_cycle.coordinator_id,
+            coordinator_name: "Starship Enterprise",
+          }
+
+          expect{ OrderCycleWebhookService.create_webhook_job(order_cycle, "order_cycle.opened") }
+            .to enqueue_job(WebhookDeliveryJob).with("http://distributor1_owner_url",
+                                                     "order_cycle.opened", hash_including(data))
+            .and enqueue_job(WebhookDeliveryJob).with("http://distributor2_owner_url",
+                                                      "order_cycle.opened", hash_including(data))
+        end
+      end
+
+      context "distributor owner is same user as coordinator owner" do
+        let(:user) { coordinator.owner }
+        let(:order_cycle) {
+          create(
+            :simple_order_cycle,
+            coordinator: coordinator,
+            distributors: [create(:distributor_enterprise, owner: user)],
+          )
+        }
+
+        it "creates only one webhook payload for the user's endpoint" do
+          user.webhook_endpoints.create! url: "http://coordinator_owner_url"
+
+          expect{ OrderCycleWebhookService.create_webhook_job(order_cycle, "order_cycle.opened") }
+            .to enqueue_job(WebhookDeliveryJob).with("http://coordinator_owner_url", any_args)
+        end
+      end
+    end
+
+    describe "suppliers" do
+      context "supplier has owner with endpoint configured" do
+        let(:order_cycle) {
+          create(
+            :simple_order_cycle,
+            coordinator: coordinator,
+            suppliers: [supplier],
+          )
+        }
+        let(:supplier) {
+          user = create(:user)
+          user.webhook_endpoints.create!(url: "http://supplier_owner_url")
+          create(:supplier_enterprise, owner: user)
+        }
+
+        it "doesn't create a webhook payload for supplier owner" do
+          expect{ OrderCycleWebhookService.create_webhook_job(order_cycle, "order_cycle.opened") }
+            .to_not enqueue_job(WebhookDeliveryJob).with("http://supplier_owner_url", any_args)
+        end
+      end
+    end
+  end
+
+  context "without webhook subscribed to enterprise" do
+    it "doesn't create webhook payload" do
+      expect{ OrderCycleWebhookService.create_webhook_job(order_cycle, "order_cycle.opened") }
+        .not_to enqueue_job(WebhookDeliveryJob)
+    end
+  end
+end
diff --git a/spec/system/consumer/account/developer_settings_spec.rb b/spec/system/consumer/account/developer_settings_spec.rb
index 4385a4aff4b..40bf4a59d63 100644
--- a/spec/system/consumer/account/developer_settings_spec.rb
+++ b/spec/system/consumer/account/developer_settings_spec.rb
@@ -35,6 +35,22 @@
           expect(page).to have_content "Key generated"
           expect(page).to have_input "api_key", with: user.reload.spree_api_key
         end
+
+        describe "Webhook Endpoints" do
+          it "creates a new webhook endpoint and deletes it" do
+            within "#webhook_endpoints" do
+              fill_in "webhook_endpoint_url", with: "https://url"
+
+              click_button I18n.t(:create)
+              expect(page.document).to have_content I18n.t('webhook_endpoints.create.success')
+              expect(page).to have_content "https://url"
+
+              click_button I18n.t(:delete)
+              expect(page.document).to have_content I18n.t('webhook_endpoints.destroy.success')
+              expect(page).to_not have_content "https://url"
+            end
+          end
+        end
       end
     end