From c21418e95cd9e4e2884f00594c39632d98392618 Mon Sep 17 00:00:00 2001
From: Alex Kozenko <9867893@gmail.com>
Date: Mon, 16 Jun 2025 17:53:39 +0300
Subject: [PATCH 01/15] Add milestone_events column to web_hooks table

---
 .../20250613162310_add_milestone_events_to_web_hooks.rb  | 9 +++++++++
 db/schema_migrations/20250613162310                      | 1 +
 db/structure.sql                                         | 1 +
 3 files changed, 11 insertions(+)
 create mode 100644 db/migrate/20250613162310_add_milestone_events_to_web_hooks.rb
 create mode 100644 db/schema_migrations/20250613162310

diff --git a/db/migrate/20250613162310_add_milestone_events_to_web_hooks.rb b/db/migrate/20250613162310_add_milestone_events_to_web_hooks.rb
new file mode 100644
index 00000000000000..bf8b24e3e399f7
--- /dev/null
+++ b/db/migrate/20250613162310_add_milestone_events_to_web_hooks.rb
@@ -0,0 +1,9 @@
+# frozen_string_literal: true
+
+class AddMilestoneEventsToWebHooks < Gitlab::Database::Migration[2.3]
+  milestone '18.1'
+
+  def change
+    add_column :web_hooks, :milestone_events, :boolean, null: false, default: false
+  end
+end
diff --git a/db/schema_migrations/20250613162310 b/db/schema_migrations/20250613162310
new file mode 100644
index 00000000000000..16d68416d52b01
--- /dev/null
+++ b/db/schema_migrations/20250613162310
@@ -0,0 +1 @@
+ecd7624a83f30d66eb361cdfa56d857162c5ff00a2f9ae3ce256013f003f4d1b
\ No newline at end of file
diff --git a/db/structure.sql b/db/structure.sql
index 7c5297872d2dc2..8db6a3ab81bf9f 100644
--- a/db/structure.sql
+++ b/db/structure.sql
@@ -25649,6 +25649,7 @@ CREATE TABLE web_hooks (
     project_events boolean DEFAULT false NOT NULL,
     vulnerability_events boolean DEFAULT false NOT NULL,
     member_approval_events boolean DEFAULT false NOT NULL,
+    milestone_events boolean DEFAULT false NOT NULL,
     CONSTRAINT check_1e4d5cbdc5 CHECK ((char_length(name) <= 255)),
     CONSTRAINT check_23a96ad211 CHECK ((char_length(description) <= 2048)),
     CONSTRAINT check_69ef76ee0c CHECK ((char_length(custom_webhook_template) <= 4096))
-- 
GitLab


From 4cd18e72040ab26a82463650c9335ebe3cf13110 Mon Sep 17 00:00:00 2001
From: Alex Kozenko <9867893@gmail.com>
Date: Mon, 16 Jun 2025 21:57:04 +0300
Subject: [PATCH 02/15] Add webhooks for project-milestones

---
 app/models/concerns/triggerable_hooks.rb      |   1 +
 app/models/hooks/project_hook.rb              |   1 +
 app/models/milestone.rb                       |   4 +
 .../integrations/project_test_data.rb         |   4 +
 .../integrations/test/project_service.rb      |   6 +-
 app/services/milestones/base_service.rb       |  12 +-
 app/services/milestones/close_service.rb      |   1 +
 app/services/milestones/create_service.rb     |   1 +
 app/services/milestones/reopen_service.rb     |   1 +
 app/services/test_hooks/project_service.rb    |   2 +
 app/views/shared/web_hooks/_form.html.haml    |   4 +
 lib/gitlab/data_builder/milestone.rb          |  36 +++++
 lib/gitlab/hook_data/milestone_builder.rb     |  29 ++++
 spec/factories/project_hooks.rb               |   1 +
 .../settings/webhooks_settings_spec.rb        |   1 +
 .../lib/gitlab/data_builder/milestone_spec.rb | 130 ++++++++++++++++++
 .../hook_data/milestone_builder_spec.rb       |  29 ++++
 .../services/milestones/close_service_spec.rb |  70 +++++++++-
 .../milestones/create_service_spec.rb         |  66 +++++++++
 .../milestones/reopen_service_spec.rb         | 105 ++++++++++++++
 .../test_hooks/project_service_spec.rb        |  12 ++
 21 files changed, 512 insertions(+), 4 deletions(-)
 create mode 100644 lib/gitlab/data_builder/milestone.rb
 create mode 100644 lib/gitlab/hook_data/milestone_builder.rb
 create mode 100644 spec/lib/gitlab/data_builder/milestone_spec.rb
 create mode 100644 spec/lib/gitlab/hook_data/milestone_builder_spec.rb
 create mode 100644 spec/services/milestones/reopen_service_spec.rb

diff --git a/app/models/concerns/triggerable_hooks.rb b/app/models/concerns/triggerable_hooks.rb
index 64e4a3311dc91c..a892593946b640 100644
--- a/app/models/concerns/triggerable_hooks.rb
+++ b/app/models/concerns/triggerable_hooks.rb
@@ -32,6 +32,7 @@ def available_triggers
         job_hooks: :job_events,
         member_hooks: :member_events,
         merge_request_hooks: :merge_requests_events,
+        milestone_hooks: :milestone_events,
         note_hooks: :note_events,
         pipeline_hooks: :pipeline_events,
         project_hooks: :project_events,
diff --git a/app/models/hooks/project_hook.rb b/app/models/hooks/project_hook.rb
index 1226a76433bfaf..c15482d071eaae 100644
--- a/app/models/hooks/project_hook.rb
+++ b/app/models/hooks/project_hook.rb
@@ -15,6 +15,7 @@ class ProjectHook < WebHook
     :issue_hooks,
     :job_hooks,
     :merge_request_hooks,
+    :milestone_hooks,
     :note_hooks,
     :pipeline_hooks,
     :push_hooks,
diff --git a/app/models/milestone.rb b/app/models/milestone.rb
index 358b479476489f..7bdbdf49f7c59a 100644
--- a/app/models/milestone.rb
+++ b/app/models/milestone.rb
@@ -99,6 +99,10 @@ class Predefined
     state :active
   end
 
+  def hook_attrs
+    Gitlab::HookData::MilestoneBuilder.new(self).build
+  end
+
   # Searches for timeboxes with a matching title.
   #
   # This method uses ILIKE on PostgreSQL
diff --git a/app/services/concerns/integrations/project_test_data.rb b/app/services/concerns/integrations/project_test_data.rb
index 185b57a1384555..f71cf87832ca43 100644
--- a/app/services/concerns/integrations/project_test_data.rb
+++ b/app/services/concerns/integrations/project_test_data.rb
@@ -82,6 +82,10 @@ def releases_events_data
       release.to_hook_data('create')
     end
 
+    def milestone_events_data
+      Gitlab::DataBuilder::Milestone.build_sample(project)
+    end
+
     def emoji_events_data
       no_data_error(s_('TestHooks|Ensure the project has notes.')) unless project.notes.any?
 
diff --git a/app/services/integrations/test/project_service.rb b/app/services/integrations/test/project_service.rb
index 1e077d49e5a0ce..ddba08e388231d 100644
--- a/app/services/integrations/test/project_service.rb
+++ b/app/services/integrations/test/project_service.rb
@@ -14,7 +14,7 @@ def project
 
       private
 
-      def data
+      def data # rubocop:disable Metrics/CyclomaticComplexity -- despite a high count of cases, this isn't that complex
         strong_memoize(:data) do
           case event || integration.default_test_event
           when 'push', 'tag_push'
@@ -35,13 +35,15 @@ def data
             deployment_events_data
           when 'release'
             releases_events_data
+          when 'milestone'
+            milestone_events_data
           when 'award_emoji'
             emoji_events_data
           when 'current_user'
             current_user_events_data
           end
         end
-      end
+      end # rubocop:enable Metrics/CyclomaticComplexity
     end
   end
 end
diff --git a/app/services/milestones/base_service.rb b/app/services/milestones/base_service.rb
index 0d7d855bf5ed3b..5be51043f5b297 100644
--- a/app/services/milestones/base_service.rb
+++ b/app/services/milestones/base_service.rb
@@ -2,14 +2,24 @@
 
 module Milestones
   class BaseService < ::BaseService
-    # Parent can either a group or a project
     attr_accessor :parent, :current_user, :params
 
     def initialize(parent, user, params = {})
       @parent = parent
       @current_user = user
       @params = params.dup
+
       super
     end
+
+    private
+
+    def execute_hooks(milestone, action)
+      return unless milestone.project_milestone?
+      return unless milestone.parent.has_active_hooks?(:milestone_hooks)
+
+      payload = Gitlab::DataBuilder::Milestone.build(milestone, action)
+      milestone.parent.execute_hooks(payload, :milestone_hooks)
+    end
   end
 end
diff --git a/app/services/milestones/close_service.rb b/app/services/milestones/close_service.rb
index a252f5c144ea14..616c6d85b7c55a 100644
--- a/app/services/milestones/close_service.rb
+++ b/app/services/milestones/close_service.rb
@@ -5,6 +5,7 @@ class CloseService < Milestones::BaseService
     def execute(milestone)
       if milestone.close && milestone.project_milestone?
         event_service.close_milestone(milestone, current_user)
+        execute_hooks(milestone, 'close')
       end
 
       milestone
diff --git a/app/services/milestones/create_service.rb b/app/services/milestones/create_service.rb
index e8a14adc10dd2d..d8a9be6aafebd4 100644
--- a/app/services/milestones/create_service.rb
+++ b/app/services/milestones/create_service.rb
@@ -9,6 +9,7 @@ def execute
 
       if milestone.save && milestone.project_milestone?
         event_service.open_milestone(milestone, current_user)
+        execute_hooks(milestone, 'create')
       end
 
       milestone
diff --git a/app/services/milestones/reopen_service.rb b/app/services/milestones/reopen_service.rb
index 125a3ec1367654..a4a9ccfd4011dc 100644
--- a/app/services/milestones/reopen_service.rb
+++ b/app/services/milestones/reopen_service.rb
@@ -5,6 +5,7 @@ class ReopenService < Milestones::BaseService
     def execute(milestone)
       if milestone.activate && milestone.project_milestone?
         event_service.reopen_milestone(milestone, current_user)
+        execute_hooks(milestone, 'reopen')
       end
 
       milestone
diff --git a/app/services/test_hooks/project_service.rb b/app/services/test_hooks/project_service.rb
index b183210edb3b54..25c81c3a498907 100644
--- a/app/services/test_hooks/project_service.rb
+++ b/app/services/test_hooks/project_service.rb
@@ -35,6 +35,8 @@ def data
           wiki_page_events_data
         when 'releases_events'
           releases_events_data
+        when 'milestone_events'
+          milestone_events_data
         when 'emoji_events'
           emoji_events_data
         when 'resource_access_token_events'
diff --git a/app/views/shared/web_hooks/_form.html.haml b/app/views/shared/web_hooks/_form.html.haml
index a3c503c9efcdc4..7c7a60adcc829b 100644
--- a/app/views/shared/web_hooks/_form.html.haml
+++ b/app/views/shared/web_hooks/_form.html.haml
@@ -58,6 +58,10 @@
       = form.gitlab_ui_checkbox_component :releases_events,
           integration_webhook_event_human_name(:releases_events),
           help_text: s_('Webhooks|A release is created, updated, or deleted.')
+    %li.gl-pb-3
+      = form.gitlab_ui_checkbox_component :milestone_events,
+          integration_webhook_event_human_name(:milestone_events),
+          help_text: s_('Webhooks|A milestone is created, closed, or reopened.')
     %li.gl-pb-3
       - emoji_help_link = link_to s_('Which emoji events trigger webhooks'), help_page_path('user/project/integrations/webhook_events.md', anchor: 'emoji-events')
       = form.gitlab_ui_checkbox_component :emoji_events,
diff --git a/lib/gitlab/data_builder/milestone.rb b/lib/gitlab/data_builder/milestone.rb
new file mode 100644
index 00000000000000..6f6e269c082513
--- /dev/null
+++ b/lib/gitlab/data_builder/milestone.rb
@@ -0,0 +1,36 @@
+# frozen_string_literal: true
+
+module Gitlab
+  module DataBuilder
+    module Milestone
+      extend self
+
+      SAMPLE_DATA = {
+        id: 1,
+        iid: 1,
+        title: 'Sample milestone',
+        description: 'Sample milestone description',
+        state: 'active',
+        created_at: Time.current,
+        updated_at: Time.current,
+        due_date: 1.week.from_now,
+        start_date: Time.current
+      }.freeze
+
+      def build(milestone, action)
+        {
+          object_kind: 'milestone',
+          event_type: 'milestone',
+          project: milestone.project&.hook_attrs,
+          object_attributes: milestone.hook_attrs,
+          action: action
+        }
+      end
+
+      def build_sample(project)
+        milestone = project.milestones.first || ::Milestone.new(SAMPLE_DATA.merge(project: project))
+        build(milestone, 'create')
+      end
+    end
+  end
+end
diff --git a/lib/gitlab/hook_data/milestone_builder.rb b/lib/gitlab/hook_data/milestone_builder.rb
new file mode 100644
index 00000000000000..f2022a956eb25b
--- /dev/null
+++ b/lib/gitlab/hook_data/milestone_builder.rb
@@ -0,0 +1,29 @@
+# frozen_string_literal: true
+
+module Gitlab
+  module HookData
+    class MilestoneBuilder < BaseBuilder
+      SAFE_HOOK_ATTRIBUTES = %i[
+        id
+        iid
+        title
+        description
+        state
+        created_at
+        updated_at
+        due_date
+        start_date
+        project_id
+      ].freeze
+
+      alias_method :milestone, :object
+
+      def build
+        milestone
+          .attributes
+          .with_indifferent_access
+          .slice(*SAFE_HOOK_ATTRIBUTES)
+      end
+    end
+  end
+end
diff --git a/spec/factories/project_hooks.rb b/spec/factories/project_hooks.rb
index 482cec1195d5ce..56959e051f828d 100644
--- a/spec/factories/project_hooks.rb
+++ b/spec/factories/project_hooks.rb
@@ -30,6 +30,7 @@
       deployment_events { true }
       feature_flag_events { true }
       releases_events { true }
+      milestone_events { true }
       emoji_events { true }
       vulnerability_events { true }
     end
diff --git a/spec/features/projects/settings/webhooks_settings_spec.rb b/spec/features/projects/settings/webhooks_settings_spec.rb
index 062bcf907960c7..f1f824a8d657e4 100644
--- a/spec/features/projects/settings/webhooks_settings_spec.rb
+++ b/spec/features/projects/settings/webhooks_settings_spec.rb
@@ -43,6 +43,7 @@
         expect(page).to have_content('Comment')
         expect(page).to have_content('Merge request events')
         expect(page).to have_content('Pipeline events')
+        expect(page).to have_content('Milestone events')
         expect(page).to have_content('Wiki page events')
         expect(page).to have_content('Releases events')
         expect(page).to have_content('Emoji events')
diff --git a/spec/lib/gitlab/data_builder/milestone_spec.rb b/spec/lib/gitlab/data_builder/milestone_spec.rb
new file mode 100644
index 00000000000000..ed750f74835477
--- /dev/null
+++ b/spec/lib/gitlab/data_builder/milestone_spec.rb
@@ -0,0 +1,130 @@
+# frozen_string_literal: true
+
+require 'spec_helper'
+
+RSpec.describe Gitlab::DataBuilder::Milestone, feature_category: :team_planning do
+  let_it_be(:project) { create(:project) }
+
+  shared_examples 'builds milestone hook data' do
+    it { expect(data).to be_a(Hash) }
+
+    it 'includes the correct structure' do
+      expect(data[:object_kind]).to eq('milestone')
+      expect(data[:event_type]).to eq('milestone')
+      expect(data[:action]).to eq(action)
+    end
+  end
+
+  describe '.build' do
+    let(:milestone) { create(:milestone, project: project) }
+    let(:action) { 'create' }
+
+    subject(:data) { described_class.build(milestone, action) }
+
+    it_behaves_like 'builds milestone hook data'
+
+    it 'includes project data' do
+      expect(data[:project]).to eq(milestone.project.hook_attrs)
+    end
+
+    it 'includes milestone attributes' do
+      object_attributes = data[:object_attributes]
+
+      expect(object_attributes[:id]).to eq(milestone.id)
+      expect(object_attributes[:iid]).to eq(milestone.iid)
+      expect(object_attributes[:title]).to eq(milestone.title)
+      expect(object_attributes[:description]).to eq(milestone.description)
+      expect(object_attributes[:state]).to eq(milestone.state)
+      expect(object_attributes[:created_at]).to eq(milestone.created_at)
+      expect(object_attributes[:updated_at]).to eq(milestone.updated_at)
+      expect(object_attributes[:due_date]).to eq(milestone.due_date)
+      expect(object_attributes[:start_date]).to eq(milestone.start_date)
+      expect(object_attributes[:project_id]).to eq(milestone.project_id)
+    end
+
+    context 'with different actions' do
+      %w[create close reopen].each do |test_action|
+        context "when action is #{test_action}" do
+          let(:action) { test_action }
+
+          it "sets the action to #{test_action}" do
+            expect(data[:action]).to eq(test_action)
+          end
+        end
+      end
+    end
+
+    context 'with milestone having dates' do
+      let(:milestone) { create(:milestone, project: project, due_date: 1.week.from_now, start_date: 1.day.ago) }
+
+      it 'includes the date information' do
+        expect(data[:object_attributes][:due_date]).to eq(milestone.due_date)
+        expect(data[:object_attributes][:start_date]).to eq(milestone.start_date)
+      end
+    end
+
+    context 'with milestone having no dates' do
+      let(:milestone) { create(:milestone, project: project, due_date: nil, start_date: nil) }
+
+      it 'includes nil date information' do
+        expect(data[:object_attributes][:due_date]).to be_nil
+        expect(data[:object_attributes][:start_date]).to be_nil
+      end
+    end
+
+    context 'with closed milestone' do
+      let(:milestone) { create(:milestone, :closed, project: project) }
+
+      it 'includes the correct state' do
+        expect(data[:object_attributes][:state]).to eq('closed')
+      end
+    end
+
+    include_examples 'project hook data'
+  end
+
+  describe '.build_sample' do
+    let(:action) { 'create' }
+
+    context 'when project has existing milestones' do
+      subject(:data) { described_class.build_sample(project) }
+
+      let!(:existing_milestone) { create(:milestone, project: project) }
+
+      it_behaves_like 'builds milestone hook data'
+
+      it 'includes project data' do
+        expect(data[:project]).to eq(project.hook_attrs)
+      end
+
+      it 'uses the first existing milestone' do
+        expect(data[:object_attributes][:id]).to eq(existing_milestone.id)
+        expect(data[:object_attributes][:title]).to eq(existing_milestone.title)
+      end
+
+      include_examples 'project hook data'
+    end
+
+    context 'when project has no milestones' do
+      subject(:data) { described_class.build_sample(clean_project) }
+
+      let(:clean_project) { create(:project, :repository) }
+
+      it_behaves_like 'builds milestone hook data'
+
+      it 'includes project data' do
+        expect(data[:project]).to eq(clean_project.hook_attrs)
+      end
+
+      it 'creates a sample milestone with predefined data' do
+        expect(data[:object_attributes][:title]).to eq('Sample milestone')
+        expect(data[:object_attributes][:description]).to eq('Sample milestone description')
+        expect(data[:object_attributes][:state]).to eq('active')
+      end
+
+      include_examples 'project hook data' do
+        let(:project) { clean_project }
+      end
+    end
+  end
+end
diff --git a/spec/lib/gitlab/hook_data/milestone_builder_spec.rb b/spec/lib/gitlab/hook_data/milestone_builder_spec.rb
new file mode 100644
index 00000000000000..ef26dc9dd5d339
--- /dev/null
+++ b/spec/lib/gitlab/hook_data/milestone_builder_spec.rb
@@ -0,0 +1,29 @@
+# frozen_string_literal: true
+
+require 'spec_helper'
+
+RSpec.describe Gitlab::HookData::MilestoneBuilder, feature_category: :webhooks do
+  let_it_be(:milestone) { create(:milestone) }
+
+  let(:builder) { described_class.new(milestone) }
+
+  describe '#build' do
+    subject(:data) { builder.build }
+
+    it 'includes safe attributes' do
+      expect(data.keys).to match_array(described_class::SAFE_HOOK_ATTRIBUTES.map(&:to_s))
+    end
+
+    it 'returns indifferent access hash' do
+      expect(data).to be_a(ActiveSupport::HashWithIndifferentAccess)
+    end
+
+    it 'includes correct milestone data' do
+      expect(data['id']).to eq(milestone.id)
+      expect(data['iid']).to eq(milestone.iid)
+      expect(data['title']).to eq(milestone.title)
+      expect(data['state']).to eq(milestone.state)
+      expect(data['project_id']).to eq(milestone.project_id)
+    end
+  end
+end
diff --git a/spec/services/milestones/close_service_spec.rb b/spec/services/milestones/close_service_spec.rb
index f362c8da6423d8..0cb302027dc0f4 100644
--- a/spec/services/milestones/close_service_spec.rb
+++ b/spec/services/milestones/close_service_spec.rb
@@ -12,8 +12,10 @@
   end
 
   describe '#execute' do
+    let(:service) { described_class.new(project, user, {}) }
+
     before do
-      described_class.new(project, user, {}).execute(milestone)
+      service.execute(milestone)
     end
 
     it { expect(milestone).to be_valid }
@@ -26,5 +28,71 @@
       it { expect(event.target).to eq(milestone) }
       it { expect(event.action_name).to eq('closed') }
     end
+
+    context 'when milestone is successfully closed' do
+      it 'executes hooks with close action' do
+        new_milestone = create(:milestone, project: project)
+
+        expect(service).to receive(:execute_hooks).with(new_milestone, 'close')
+
+        service.execute(new_milestone)
+      end
+    end
+
+    context 'when milestone fails to close' do
+      it 'does not execute hooks' do
+        closed_milestone = create(:milestone, :closed, project: project)
+
+        expect(service).not_to receive(:execute_hooks)
+
+        service.execute(closed_milestone)
+      end
+    end
+  end
+
+  describe 'webhook execution' do
+    let(:service) { described_class.new(project, user, {}) }
+
+    context 'when project has active milestone hooks' do
+      before do
+        create(:project_hook, project: project, milestone_events: true)
+      end
+
+      it 'executes milestone hooks with correct payload when conditions are met' do
+        allow(milestone).to receive(:project_milestone?).and_return(true)
+        allow(project).to receive(:has_active_hooks?).with(:milestone_hooks).and_return(true)
+
+        expected_payload = Gitlab::DataBuilder::Milestone.build(milestone, 'close')
+
+        expect(project).to receive(:execute_hooks).with(expected_payload, :milestone_hooks)
+
+        service.send(:execute_hooks, milestone, 'close')
+      end
+    end
+
+    context 'when project has no active milestone hooks' do
+      it 'does not execute hooks when no active hooks' do
+        allow(milestone).to receive(:project_milestone?).and_return(true)
+        allow(project).to receive(:has_active_hooks?).with(:milestone_hooks).and_return(false)
+
+        expect(project).not_to receive(:execute_hooks)
+
+        service.send(:execute_hooks, milestone, 'close')
+      end
+    end
+
+    context 'when milestone is a group milestone' do
+      let(:group) { create(:group) }
+      let(:group_milestone) { create(:milestone, group: group) }
+      let(:group_service) { described_class.new(group, user, {}) }
+
+      it 'does not execute hooks for group milestones' do
+        allow(group_milestone).to receive(:project_milestone?).and_return(false)
+
+        expect(group).not_to receive(:execute_hooks)
+
+        group_service.send(:execute_hooks, group_milestone, 'close')
+      end
+    end
   end
 end
diff --git a/spec/services/milestones/create_service_spec.rb b/spec/services/milestones/create_service_spec.rb
index 70010d88fbd3b3..34f449a9135877 100644
--- a/spec/services/milestones/create_service_spec.rb
+++ b/spec/services/milestones/create_service_spec.rb
@@ -29,6 +29,12 @@
         expect(milestone.title).to eq('New Milestone')
         expect(milestone.description).to eq('Description')
       end
+
+      it 'executes hooks with create action' do
+        expect(create_milestone).to receive(:execute_hooks).with(kind_of(Milestone), 'create')
+
+        create_milestone.execute
+      end
     end
 
     context 'when milestone fails to save' do
@@ -48,6 +54,12 @@
         create_milestone.execute
       end
 
+      it 'does not execute hooks' do
+        expect(create_milestone).not_to receive(:execute_hooks)
+
+        create_milestone.execute
+      end
+
       it 'returns the unsaved milestone' do
         milestone = create_milestone.execute
         expect(milestone).to be_a(Milestone)
@@ -62,6 +74,60 @@
     end
   end
 
+  describe 'webhook execution' do
+    let(:milestone) { create(:milestone, project: project) }
+
+    context 'when project has active milestone hooks' do
+      before do
+        create(:project_hook, project: project, milestone_events: true)
+      end
+
+      it 'executes milestone hooks with correct payload when conditions are met' do
+        allow(milestone).to receive(:project_milestone?).and_return(true)
+        allow(project).to receive(:has_active_hooks?).with(:milestone_hooks).and_return(true)
+        expected_payload = Gitlab::DataBuilder::Milestone.build(milestone, 'create')
+
+        expect(project).to receive(:execute_hooks).with(expected_payload, :milestone_hooks)
+
+        create_milestone.send(:execute_hooks, milestone, 'create')
+      end
+
+      it 'only executes hooks for project milestones' do
+        allow(milestone).to receive(:project_milestone?).and_return(true)
+
+        expect(project).to receive(:has_active_hooks?).with(:milestone_hooks).and_return(true)
+        expect(project).to receive(:execute_hooks)
+
+        create_milestone.send(:execute_hooks, milestone, 'create')
+      end
+    end
+
+    context 'when project has no active milestone hooks' do
+      it 'does not execute hooks when no active hooks' do
+        allow(milestone).to receive(:project_milestone?).and_return(true)
+        allow(project).to receive(:has_active_hooks?).with(:milestone_hooks).and_return(false)
+
+        expect(project).not_to receive(:execute_hooks)
+
+        create_milestone.send(:execute_hooks, milestone, 'create')
+      end
+    end
+
+    context 'when milestone is a group milestone' do
+      let(:group) { create(:group) }
+      let(:group_milestone) { create(:milestone, group: group) }
+      let(:group_service) { described_class.new(group, user, params) }
+
+      it 'does not execute hooks for group milestones' do
+        allow(group_milestone).to receive(:project_milestone?).and_return(false)
+
+        expect(group).not_to receive(:execute_hooks)
+
+        group_service.send(:execute_hooks, group_milestone, 'create')
+      end
+    end
+  end
+
   describe '#before_create' do
     it 'checks for spam' do
       milestone = build(:milestone)
diff --git a/spec/services/milestones/reopen_service_spec.rb b/spec/services/milestones/reopen_service_spec.rb
new file mode 100644
index 00000000000000..c9db97a94a7279
--- /dev/null
+++ b/spec/services/milestones/reopen_service_spec.rb
@@ -0,0 +1,105 @@
+# frozen_string_literal: true
+
+require 'spec_helper'
+
+RSpec.describe Milestones::ReopenService, feature_category: :team_planning do
+  let(:user) { create(:user) }
+  let(:project) { create(:project) }
+  let(:milestone) { create(:milestone, :closed, title: "Milestone v1.2", project: project) }
+
+  before do
+    project.add_maintainer(user)
+  end
+
+  describe '#execute' do
+    let(:service) { described_class.new(project, user, {}) }
+
+    before do
+      service.execute(milestone)
+    end
+
+    it { expect(milestone).to be_valid }
+    it { expect(milestone).to be_active }
+
+    describe 'event' do
+      let(:event) { Event.recent.first }
+
+      it { expect(event.milestone).to be_truthy }
+      it { expect(event.target).to eq(milestone) }
+      it { expect(event.action_name).to eq('opened') }
+    end
+
+    context 'when milestone is successfully reopened' do
+      it 'executes hooks with reopen action' do
+        closed_milestone = create(:milestone, :closed, project: project)
+
+        expect(service).to receive(:execute_hooks).with(closed_milestone, 'reopen')
+
+        service.execute(closed_milestone)
+      end
+    end
+
+    context 'when milestone fails to reopen' do
+      it 'does not execute hooks' do
+        active_milestone = create(:milestone, project: project)
+
+        expect(service).not_to receive(:execute_hooks)
+
+        service.execute(active_milestone)
+      end
+    end
+  end
+
+  describe 'webhook execution' do
+    let(:service) { described_class.new(project, user, {}) }
+
+    context 'when project has active milestone hooks' do
+      before do
+        create(:project_hook, project: project, milestone_events: true)
+      end
+
+      it 'executes milestone hooks with correct payload when conditions are met' do
+        allow(milestone).to receive(:project_milestone?).and_return(true)
+        allow(project).to receive(:has_active_hooks?).with(:milestone_hooks).and_return(true)
+        expected_payload = Gitlab::DataBuilder::Milestone.build(milestone, 'reopen')
+
+        expect(project).to receive(:execute_hooks).with(expected_payload, :milestone_hooks)
+
+        service.send(:execute_hooks, milestone, 'reopen')
+      end
+
+      it 'only executes hooks for project milestones' do
+        allow(milestone).to receive(:project_milestone?).and_return(true)
+        expect(project).to receive(:has_active_hooks?).with(:milestone_hooks).and_return(true)
+        expect(project).to receive(:execute_hooks)
+
+        service.send(:execute_hooks, milestone, 'reopen')
+      end
+    end
+
+    context 'when project has no active milestone hooks' do
+      it 'does not execute hooks when no active hooks' do
+        allow(milestone).to receive(:project_milestone?).and_return(true)
+        allow(project).to receive(:has_active_hooks?).with(:milestone_hooks).and_return(false)
+
+        expect(project).not_to receive(:execute_hooks)
+
+        service.send(:execute_hooks, milestone, 'reopen')
+      end
+    end
+
+    context 'when milestone is a group milestone' do
+      let(:group) { create(:group) }
+      let(:group_milestone) { create(:milestone, :closed, group: group) }
+      let(:group_service) { described_class.new(group, user, {}) }
+
+      it 'does not execute hooks for group milestones' do
+        allow(group_milestone).to receive(:project_milestone?).and_return(false)
+
+        expect(group).not_to receive(:execute_hooks)
+
+        group_service.send(:execute_hooks, group_milestone, 'reopen')
+      end
+    end
+  end
+end
diff --git a/spec/services/test_hooks/project_service_spec.rb b/spec/services/test_hooks/project_service_spec.rb
index 1e06911f8f799c..cd2bc14c0edeca 100644
--- a/spec/services/test_hooks/project_service_spec.rb
+++ b/spec/services/test_hooks/project_service_spec.rb
@@ -211,6 +211,18 @@
       end
     end
 
+    context 'milestone_events' do
+      let(:trigger) { 'milestone_events' }
+      let(:trigger_key) { :milestone_hooks }
+
+      it 'executes hook' do
+        allow(Gitlab::DataBuilder::Milestone).to receive(:build_sample).and_return(sample_data)
+
+        expect(hook).to receive(:execute).with(sample_data, trigger_key, force: true).and_return(success_result)
+        expect(service.execute).to include(success_result)
+      end
+    end
+
     context 'emoji' do
       let(:trigger) { 'emoji_events' }
       let(:trigger_key) { :emoji_hooks }
-- 
GitLab


From 5b80bb2be1050fd1ba0410d1d0375012472911c4 Mon Sep 17 00:00:00 2001
From: Alex Kozenko <9867893@gmail.com>
Date: Mon, 16 Jun 2025 22:03:28 +0300
Subject: [PATCH 03/15] Add info about milestone_events to REST API

---
 lib/api/entities/project_hook.rb                               | 1 +
 lib/api/project_hooks.rb                                       | 1 +
 spec/fixtures/api/schemas/public_api/v4/project_hook.json      | 3 +++
 spec/lib/gitlab/import_export/project/relation_factory_spec.rb | 1 +
 spec/lib/gitlab/import_export/safe_model_attributes.yml        | 1 +
 5 files changed, 7 insertions(+)

diff --git a/lib/api/entities/project_hook.rb b/lib/api/entities/project_hook.rb
index a1ede6fe277176..b81720fa28f7fb 100644
--- a/lib/api/entities/project_hook.rb
+++ b/lib/api/entities/project_hook.rb
@@ -14,6 +14,7 @@ class ProjectHook < Hook
       expose :feature_flag_events, documentation: { type: 'boolean' }
       expose :job_events, documentation: { type: 'boolean' }
       expose :releases_events, documentation: { type: 'boolean' }
+      expose :milestone_events, documentation: { type: 'boolean' }
       expose :emoji_events, documentation: { type: 'boolean' }
       expose :resource_access_token_events, documentation: { type: 'boolean' }
       expose :vulnerability_events, documentation: { type: 'boolean' }
diff --git a/lib/api/project_hooks.rb b/lib/api/project_hooks.rb
index ecd32e9155f849..ceffa33a63dcc3 100644
--- a/lib/api/project_hooks.rb
+++ b/lib/api/project_hooks.rb
@@ -37,6 +37,7 @@ def hook_scope
         optional :deployment_events, type: Boolean, desc: "Trigger hook on deployment events"
         optional :feature_flag_events, type: Boolean, desc: "Trigger hook on feature flag events"
         optional :releases_events, type: Boolean, desc: "Trigger hook on release events"
+        optional :milestone_events, type: Boolean, desc: "Trigger hook on milestone events"
         optional :emoji_events, type: Boolean, desc: "Trigger hook on emoji events"
         optional :resource_access_token_events, type: Boolean, desc: "Trigger hook on project access token expiry events"
         optional :enable_ssl_verification, type: Boolean, desc: "Do SSL verification when triggering the hook"
diff --git a/spec/fixtures/api/schemas/public_api/v4/project_hook.json b/spec/fixtures/api/schemas/public_api/v4/project_hook.json
index 238f5839f77dfb..fb9cc717288685 100644
--- a/spec/fixtures/api/schemas/public_api/v4/project_hook.json
+++ b/spec/fixtures/api/schemas/public_api/v4/project_hook.json
@@ -117,6 +117,9 @@
     "releases_events": {
       "type": "boolean"
     },
+    "milestone_events": {
+      "type": "boolean"
+    },
     "emoji_events": {
       "type": "boolean"
     },
diff --git a/spec/lib/gitlab/import_export/project/relation_factory_spec.rb b/spec/lib/gitlab/import_export/project/relation_factory_spec.rb
index f898b18e20035d..439fedd3243226 100644
--- a/spec/lib/gitlab/import_export/project/relation_factory_spec.rb
+++ b/spec/lib/gitlab/import_export/project/relation_factory_spec.rb
@@ -67,6 +67,7 @@ def values
         'job_events' => false,
         'wiki_page_events' => true,
         'releases_events' => false,
+        'milestone_events' => false,
         'emoji_events' => false,
         'resource_access_token_events' => false,
         'token' => token
diff --git a/spec/lib/gitlab/import_export/safe_model_attributes.yml b/spec/lib/gitlab/import_export/safe_model_attributes.yml
index 0de163942df879..1ef6ed465cd8f3 100644
--- a/spec/lib/gitlab/import_export/safe_model_attributes.yml
+++ b/spec/lib/gitlab/import_export/safe_model_attributes.yml
@@ -619,6 +619,7 @@ ProjectHook:
 - confidential_note_events
 - repository_update_events
 - releases_events
+- milestone_events
 - emoji_events
 - resource_access_token_events
 ProtectedBranch:
-- 
GitLab


From a4ef74fc9c723c640d8765a1a2995fb4a1d0fb41 Mon Sep 17 00:00:00 2001
From: Alex Kozenko <9867893@gmail.com>
Date: Mon, 16 Jun 2025 22:08:08 +0300
Subject: [PATCH 04/15] Add info about milestone webhooks to documentation

---
 doc/api/project_webhooks.md                   |  5 +-
 .../project/integrations/webhook_events.md    | 58 +++++++++++++++++++
 2 files changed, 62 insertions(+), 1 deletion(-)

diff --git a/doc/api/project_webhooks.md b/doc/api/project_webhooks.md
index 612ff5516beb53..9d5173660cef8e 100644
--- a/doc/api/project_webhooks.md
+++ b/doc/api/project_webhooks.md
@@ -70,6 +70,7 @@ Example response:
   "wiki_page_events": true,
   "deployment_events": true,
   "releases_events": true,
+  "milestone_events": true,
   "feature_flag_events": true,
   "enable_ssl_verification": true,
   "repository_update_events": false,
@@ -431,6 +432,7 @@ Supported attributes:
 | `branch_filter_strategy`       | string            | No       | Filter push events by branch. Possible values are `wildcard` (default), `regex`, and `all_branches`. |
 | `push_events`                  | boolean           | No       | Trigger project webhook on push events. |
 | `releases_events`              | boolean           | No       | Trigger project webhook on release events. |
+| `milestone_events`             | boolean           | No       | Trigger project webhook on milestone events. |
 | `tag_push_events`              | boolean           | No       | Trigger project webhook on tag push events. |
 | `token`                        | string            | No       | Secret token to validate received payloads; the token isn't returned in the response. |
 | `wiki_page_events`             | boolean           | No       | Trigger project webhook on wiki events. |
@@ -475,6 +477,7 @@ Supported attributes:
 | `branch_filter_strategy`       | string            | No       | Filter push events by branch. Possible values are `wildcard` (default), `regex`, and `all_branches`. |
 | `push_events`                  | boolean           | No       | Trigger project webhook on push events. |
 | `releases_events`              | boolean           | No       | Trigger project webhook on release events. |
+| `milestone_events`             | boolean           | No       | Trigger project webhook on milestone events. |
 | `tag_push_events`              | boolean           | No       | Trigger project webhook on tag push events. |
 | `token`                        | string            | No       | Secret token to validate received payloads. Not returned in the response. When you change the webhook URL, the secret token is reset and not retained. |
 | `wiki_page_events`             | boolean           | No       | Trigger project webhook on wiki page events. |
@@ -531,7 +534,7 @@ Supported attributes:
 |:----------|:------------------|:---------|:------------|
 | `hook_id` | integer           | Yes      | ID of the project webhook. |
 | `id`      | integer or string | Yes      | ID or [URL-encoded path of the project](rest/_index.md#namespaced-paths). |
-| `trigger` | string            | Yes      | One of `push_events`, `tag_push_events`, `issues_events`, `confidential_issues_events`, `note_events`, `merge_requests_events`, `job_events`, `pipeline_events`, `wiki_page_events`, `releases_events`, `emoji_events`, or `resource_access_token_events`. |
+| `trigger` | string            | Yes      | One of `push_events`, `tag_push_events`, `issues_events`, `confidential_issues_events`, `note_events`, `merge_requests_events`, `job_events`, `pipeline_events`, `wiki_page_events`, `releases_events`, `milestone_events`, `emoji_events`, or `resource_access_token_events`. |
 
 Example response:
 
diff --git a/doc/user/project/integrations/webhook_events.md b/doc/user/project/integrations/webhook_events.md
index 6d36f967f5fcc5..a52a89081071e8 100644
--- a/doc/user/project/integrations/webhook_events.md
+++ b/doc/user/project/integrations/webhook_events.md
@@ -37,6 +37,7 @@ Event type                                   | Trigger
 [Deployment event](#deployment-events)       | A deployment starts, succeeds, fails, or is canceled.
 [Feature flag event](#feature-flag-events)   | A feature flag is turned on or off.
 [Release event](#release-events)             | A release is created, edited, or deleted.
+[Milestone event](#milestone-events)         | A milestone is created, closed, or reopened.
 [Emoji event](#emoji-events)                 | An emoji reaction is added or removed.
 [Project or group access token event](#project-and-group-access-token-events) | A project or group access token will expire in seven days.
 [Vulnerability event](#vulnerability-events) | A vulnerability is created or updated.
@@ -2137,6 +2138,63 @@ Payload example:
 }
 ```
 
+## Milestone events
+
+Milestone events are triggered when a milestone is created, closed, or reopened.
+
+The available values for `object_attributes.action` in the payload are:
+
+- `create`
+- `close`
+- `reopen`
+
+Request header:
+
+```plaintext
+X-Gitlab-Event: Milestone Hook
+```
+
+Payload example:
+
+```json
+{
+  "object_kind": "milestone",
+  "event_type": "milestone",
+  "project": {
+    "id": 1,
+    "name": "Gitlab Test",
+    "description": "Aut reprehenderit ut est.",
+    "web_url": "http://example.com/gitlabhq/gitlab-test",
+    "avatar_url": null,
+    "git_ssh_url": "git@example.com:gitlabhq/gitlab-test.git",
+    "git_http_url": "http://example.com/gitlabhq/gitlab-test.git",
+    "namespace": "GitlabHQ",
+    "visibility_level": 20,
+    "path_with_namespace": "gitlabhq/gitlab-test",
+    "default_branch": "master",
+    "ci_config_path": null,
+    "homepage": "http://example.com/gitlabhq/gitlab-test",
+    "url": "http://example.com/gitlabhq/gitlab-test.git",
+    "ssh_url": "git@example.com:gitlabhq/gitlab-test.git",
+    "http_url": "http://example.com/gitlabhq/gitlab-test.git"
+  },
+  "object_attributes": {
+    "id": 61,
+    "iid": 10,
+    "title": "v1.0",
+    "description": "First stable release",
+    "state": "active",
+    "created_at": "2025-06-16 14:10:57 UTC",
+    "updated_at": "2025-06-16 14:10:57 UTC",
+    "due_date": "2025-06-30",
+    "start_date": "2025-06-16",
+    "group_id": null,
+    "project_id": 1
+  },
+  "action": "create"
+}
+```
+
 ## Emoji events
 
 {{< history >}}
-- 
GitLab


From 236889e70bd0bb3a373cf97536c750b4cc4aad5a Mon Sep 17 00:00:00 2001
From: Alex Kozenko <9867893@gmail.com>
Date: Mon, 16 Jun 2025 22:14:56 +0300
Subject: [PATCH 05/15] Update gitlab.pot

---
 locale/gitlab.pot | 3 +++
 1 file changed, 3 insertions(+)

diff --git a/locale/gitlab.pot b/locale/gitlab.pot
index ef04cd43442775..952a65ae5a7f7d 100644
--- a/locale/gitlab.pot
+++ b/locale/gitlab.pot
@@ -69032,6 +69032,9 @@ msgstr ""
 msgid "Webhooks|A merge request is created, updated, or merged."
 msgstr ""
 
+msgid "Webhooks|A milestone is created, closed, or reopened."
+msgstr ""
+
 msgid "Webhooks|A new tag is pushed to the repository."
 msgstr ""
 
-- 
GitLab


From b1ae109a721683579f289d7e476613614b3436b3 Mon Sep 17 00:00:00 2001
From: Alex Kozenko <9867893@gmail.com>
Date: Tue, 17 Jun 2025 12:27:02 +0300
Subject: [PATCH 06/15] Update OpenAPI documentation

---
 doc/api/openapi/openapi_v2.yaml | 9 +++++++++
 1 file changed, 9 insertions(+)

diff --git a/doc/api/openapi/openapi_v2.yaml b/doc/api/openapi/openapi_v2.yaml
index a8206c01ef1985..9e8a143724190a 100644
--- a/doc/api/openapi/openapi_v2.yaml
+++ b/doc/api/openapi/openapi_v2.yaml
@@ -29119,6 +29119,7 @@ paths:
         - issues_events
         - job_events
         - merge_requests_events
+        - milestone_events
         - note_events
         - pipeline_events
         - push_events
@@ -59191,6 +59192,8 @@ definitions:
         type: boolean
       releases_events:
         type: boolean
+      milestone_events:
+        type: boolean
       emoji_events:
         type: boolean
       resource_access_token_events:
@@ -59249,6 +59252,9 @@ definitions:
       releases_events:
         type: boolean
         description: Trigger hook on release events
+      milestone_events:
+        type: boolean
+        description: Trigger hook on milestone events
       emoji_events:
         type: boolean
         description: Trigger hook on emoji events
@@ -59366,6 +59372,9 @@ definitions:
       releases_events:
         type: boolean
         description: Trigger hook on release events
+      milestone_events:
+        type: boolean
+        description: Trigger hook on milestone events
       emoji_events:
         type: boolean
         description: Trigger hook on emoji events
-- 
GitLab


From 49a897a9c427cd6266c8d05e6fdea242943779de Mon Sep 17 00:00:00 2001
From: Alex Kozenko <9867893@gmail.com>
Date: Tue, 17 Jun 2025 12:33:37 +0300
Subject: [PATCH 07/15] Polish up milestone services specs

---
 app/services/milestones/base_service.rb         |  1 +
 spec/services/milestones/close_service_spec.rb  |  8 ++++----
 spec/services/milestones/create_service_spec.rb | 12 +++++-------
 spec/services/milestones/reopen_service_spec.rb |  8 ++++----
 4 files changed, 14 insertions(+), 15 deletions(-)

diff --git a/app/services/milestones/base_service.rb b/app/services/milestones/base_service.rb
index 5be51043f5b297..1b3aa1ef777243 100644
--- a/app/services/milestones/base_service.rb
+++ b/app/services/milestones/base_service.rb
@@ -5,6 +5,7 @@ class BaseService < ::BaseService
     attr_accessor :parent, :current_user, :params
 
     def initialize(parent, user, params = {})
+      # Parent can either a group or a project
       @parent = parent
       @current_user = user
       @params = params.dup
diff --git a/spec/services/milestones/close_service_spec.rb b/spec/services/milestones/close_service_spec.rb
index 0cb302027dc0f4..6eb327d01ea2be 100644
--- a/spec/services/milestones/close_service_spec.rb
+++ b/spec/services/milestones/close_service_spec.rb
@@ -30,22 +30,22 @@
     end
 
     context 'when milestone is successfully closed' do
-      it 'executes hooks with close action' do
+      it 'executes hooks with close action and creates new event' do
         new_milestone = create(:milestone, project: project)
 
         expect(service).to receive(:execute_hooks).with(new_milestone, 'close')
 
-        service.execute(new_milestone)
+        expect { service.execute(new_milestone) }.to change { Event.count }.by(1)
       end
     end
 
     context 'when milestone fails to close' do
-      it 'does not execute hooks' do
+      it 'does not execute hooks and does not create new event' do
         closed_milestone = create(:milestone, :closed, project: project)
 
         expect(service).not_to receive(:execute_hooks)
 
-        service.execute(closed_milestone)
+        expect { service.execute(closed_milestone) }.not_to change { Event.count }
       end
     end
   end
diff --git a/spec/services/milestones/create_service_spec.rb b/spec/services/milestones/create_service_spec.rb
index 34f449a9135877..2f8c1df09a587e 100644
--- a/spec/services/milestones/create_service_spec.rb
+++ b/spec/services/milestones/create_service_spec.rb
@@ -30,10 +30,10 @@
         expect(milestone.description).to eq('Description')
       end
 
-      it 'executes hooks with create action' do
+      it 'executes hooks with create action and creates new event' do
         expect(create_milestone).to receive(:execute_hooks).with(kind_of(Milestone), 'create')
 
-        create_milestone.execute
+        expect { create_milestone.execute }.to change { Event.count }.by(1)
       end
     end
 
@@ -54,10 +54,10 @@
         create_milestone.execute
       end
 
-      it 'does not execute hooks' do
+      it 'does not execute hooks and does not create new event' do
         expect(create_milestone).not_to receive(:execute_hooks)
 
-        create_milestone.execute
+        expect { create_milestone.execute }.not_to change { Event.count }
       end
 
       it 'returns the unsaved milestone' do
@@ -92,7 +92,7 @@
         create_milestone.send(:execute_hooks, milestone, 'create')
       end
 
-      it 'only executes hooks for project milestones' do
+      it 'only executes active hooks for project milestones' do
         allow(milestone).to receive(:project_milestone?).and_return(true)
 
         expect(project).to receive(:has_active_hooks?).with(:milestone_hooks).and_return(true)
@@ -119,8 +119,6 @@
       let(:group_service) { described_class.new(group, user, params) }
 
       it 'does not execute hooks for group milestones' do
-        allow(group_milestone).to receive(:project_milestone?).and_return(false)
-
         expect(group).not_to receive(:execute_hooks)
 
         group_service.send(:execute_hooks, group_milestone, 'create')
diff --git a/spec/services/milestones/reopen_service_spec.rb b/spec/services/milestones/reopen_service_spec.rb
index c9db97a94a7279..ceded7275fabf5 100644
--- a/spec/services/milestones/reopen_service_spec.rb
+++ b/spec/services/milestones/reopen_service_spec.rb
@@ -30,22 +30,22 @@
     end
 
     context 'when milestone is successfully reopened' do
-      it 'executes hooks with reopen action' do
+      it 'executes hooks with reopen action and creates new event' do
         closed_milestone = create(:milestone, :closed, project: project)
 
         expect(service).to receive(:execute_hooks).with(closed_milestone, 'reopen')
 
-        service.execute(closed_milestone)
+        expect { service.execute(closed_milestone) }.to change { Event.count }.by(1)
       end
     end
 
     context 'when milestone fails to reopen' do
-      it 'does not execute hooks' do
+      it 'does not execute hooks and does not create new event' do
         active_milestone = create(:milestone, project: project)
 
         expect(service).not_to receive(:execute_hooks)
 
-        service.execute(active_milestone)
+        expect { service.execute(active_milestone) }.not_to change { Event.count }
       end
     end
   end
-- 
GitLab


From e0485eff11af1a435f4509971ddca6898c3e34d6 Mon Sep 17 00:00:00 2001
From: Alex Kozenko <9867893@gmail.com>
Date: Tue, 17 Jun 2025 13:30:56 +0300
Subject: [PATCH 08/15] Apply Danger Bot suggestions

---
 spec/lib/gitlab/data_builder/milestone_spec.rb  | 4 ++--
 spec/services/milestones/reopen_service_spec.rb | 7 ++++---
 2 files changed, 6 insertions(+), 5 deletions(-)

diff --git a/spec/lib/gitlab/data_builder/milestone_spec.rb b/spec/lib/gitlab/data_builder/milestone_spec.rb
index ed750f74835477..8eb13c8ac42811 100644
--- a/spec/lib/gitlab/data_builder/milestone_spec.rb
+++ b/spec/lib/gitlab/data_builder/milestone_spec.rb
@@ -89,7 +89,7 @@
     context 'when project has existing milestones' do
       subject(:data) { described_class.build_sample(project) }
 
-      let!(:existing_milestone) { create(:milestone, project: project) }
+      let_it_be(:existing_milestone) { create(:milestone, project: project) }
 
       it_behaves_like 'builds milestone hook data'
 
@@ -108,7 +108,7 @@
     context 'when project has no milestones' do
       subject(:data) { described_class.build_sample(clean_project) }
 
-      let(:clean_project) { create(:project, :repository) }
+      let_it_be(:clean_project) { create(:project) }
 
       it_behaves_like 'builds milestone hook data'
 
diff --git a/spec/services/milestones/reopen_service_spec.rb b/spec/services/milestones/reopen_service_spec.rb
index ceded7275fabf5..199ad404bc7a8f 100644
--- a/spec/services/milestones/reopen_service_spec.rb
+++ b/spec/services/milestones/reopen_service_spec.rb
@@ -3,11 +3,12 @@
 require 'spec_helper'
 
 RSpec.describe Milestones::ReopenService, feature_category: :team_planning do
-  let(:user) { create(:user) }
-  let(:project) { create(:project) }
+  let_it_be(:project) { create(:project) }
+  let_it_be(:user) { create(:user) }
+
   let(:milestone) { create(:milestone, :closed, title: "Milestone v1.2", project: project) }
 
-  before do
+  before_all do
     project.add_maintainer(user)
   end
 
-- 
GitLab


From 73e8c861425473ae5523bb1e435b96bea3cab868 Mon Sep 17 00:00:00 2001
From: Alex Kozenko <9867893@gmail.com>
Date: Tue, 17 Jun 2025 16:01:19 +0300
Subject: [PATCH 09/15] Apply GitLabDuo suggestion - add comment

---
 app/services/milestones/base_service.rb | 1 +
 1 file changed, 1 insertion(+)

diff --git a/app/services/milestones/base_service.rb b/app/services/milestones/base_service.rb
index 1b3aa1ef777243..ecfe7db325e514 100644
--- a/app/services/milestones/base_service.rb
+++ b/app/services/milestones/base_service.rb
@@ -16,6 +16,7 @@ def initialize(parent, user, params = {})
     private
 
     def execute_hooks(milestone, action)
+      # At the moment, only project milestones support webhooks, not group milestones
       return unless milestone.project_milestone?
       return unless milestone.parent.has_active_hooks?(:milestone_hooks)
 
-- 
GitLab


From c6b1b33172899896223e5452ec2563edb7121605 Mon Sep 17 00:00:00 2001
From: Alex Kozenko <9867893@gmail.com>
Date: Fri, 20 Jun 2025 17:01:26 +0300
Subject: [PATCH 10/15] Apply CR suggestions for milestone webhooks

---
 ...62310_add_milestone_events_to_web_hooks.rb |  2 +-
 .../services/milestones/close_service_spec.rb | 90 ++++++++----------
 .../milestones/create_service_spec.rb         | 80 ++++++----------
 .../milestones/reopen_service_spec.rb         | 95 ++++++++-----------
 4 files changed, 105 insertions(+), 162 deletions(-)

diff --git a/db/migrate/20250613162310_add_milestone_events_to_web_hooks.rb b/db/migrate/20250613162310_add_milestone_events_to_web_hooks.rb
index bf8b24e3e399f7..0357de580ff518 100644
--- a/db/migrate/20250613162310_add_milestone_events_to_web_hooks.rb
+++ b/db/migrate/20250613162310_add_milestone_events_to_web_hooks.rb
@@ -1,7 +1,7 @@
 # frozen_string_literal: true
 
 class AddMilestoneEventsToWebHooks < Gitlab::Database::Migration[2.3]
-  milestone '18.1'
+  milestone '18.2'
 
   def change
     add_column :web_hooks, :milestone_events, :boolean, null: false, default: false
diff --git a/spec/services/milestones/close_service_spec.rb b/spec/services/milestones/close_service_spec.rb
index 6eb327d01ea2be..2c0caa38bb6ec3 100644
--- a/spec/services/milestones/close_service_spec.rb
+++ b/spec/services/milestones/close_service_spec.rb
@@ -14,84 +14,68 @@
   describe '#execute' do
     let(:service) { described_class.new(project, user, {}) }
 
-    before do
-      service.execute(milestone)
-    end
+    context 'when service is called before test suite' do
+      before do
+        service.execute(milestone)
+      end
 
-    it { expect(milestone).to be_valid }
-    it { expect(milestone).to be_closed }
+      it { expect(milestone).to be_valid }
+      it { expect(milestone).to be_closed }
 
-    describe 'event' do
-      let(:event) { Event.recent.first }
+      describe 'event' do
+        let(:event) { Event.recent.first }
 
-      it { expect(event.milestone).to be_truthy }
-      it { expect(event.target).to eq(milestone) }
-      it { expect(event.action_name).to eq('closed') }
+        it { expect(event.milestone).to be_truthy }
+        it { expect(event.target).to eq(milestone) }
+        it { expect(event.action_name).to eq('closed') }
+      end
     end
 
-    context 'when milestone is successfully closed' do
+    shared_examples 'closes the milestone' do |with_project_hooks:|
       it 'executes hooks with close action and creates new event' do
-        new_milestone = create(:milestone, project: project)
-
-        expect(service).to receive(:execute_hooks).with(new_milestone, 'close')
+        expect(service).to receive(:execute_hooks).with(milestone, 'close').and_call_original
+        expect(project).to receive(:execute_hooks).with(kind_of(Hash), :milestone_hooks) if with_project_hooks
 
-        expect { service.execute(new_milestone) }.to change { Event.count }.by(1)
+        expect { service.execute(milestone) }.to change { Event.count }.by(1)
       end
     end
 
-    context 'when milestone fails to close' do
+    shared_examples 'does not close the milestone' do
       it 'does not execute hooks and does not create new event' do
-        closed_milestone = create(:milestone, :closed, project: project)
-
         expect(service).not_to receive(:execute_hooks)
 
-        expect { service.execute(closed_milestone) }.not_to change { Event.count }
+        expect { service.execute(milestone) }.not_to change { Event.count }
       end
     end
-  end
-
-  describe 'webhook execution' do
-    let(:service) { described_class.new(project, user, {}) }
 
-    context 'when project has active milestone hooks' do
-      before do
-        create(:project_hook, project: project, milestone_events: true)
+    context 'when milestone is successfully closed' do
+      context 'when project has active milestone hooks' do
+        let(:project) do
+          create(:project).tap do |project|
+            create(:project_hook, project: project, milestone_events: true)
+          end
+        end
+
+        it_behaves_like 'closes the milestone', with_project_hooks: true
       end
 
-      it 'executes milestone hooks with correct payload when conditions are met' do
-        allow(milestone).to receive(:project_milestone?).and_return(true)
-        allow(project).to receive(:has_active_hooks?).with(:milestone_hooks).and_return(true)
-
-        expected_payload = Gitlab::DataBuilder::Milestone.build(milestone, 'close')
-
-        expect(project).to receive(:execute_hooks).with(expected_payload, :milestone_hooks)
-
-        service.send(:execute_hooks, milestone, 'close')
+      context 'when project has no active milestone hooks' do
+        it_behaves_like 'closes the milestone', with_project_hooks: false
       end
     end
 
-    context 'when project has no active milestone hooks' do
-      it 'does not execute hooks when no active hooks' do
-        allow(milestone).to receive(:project_milestone?).and_return(true)
-        allow(project).to receive(:has_active_hooks?).with(:milestone_hooks).and_return(false)
-
-        expect(project).not_to receive(:execute_hooks)
+    context 'when milestone fails to close' do
+      context 'when milestone is already closed' do
+        let(:milestone) { create(:milestone, :closed, project: project) }
 
-        service.send(:execute_hooks, milestone, 'close')
+        it_behaves_like 'does not close the milestone'
       end
-    end
-
-    context 'when milestone is a group milestone' do
-      let(:group) { create(:group) }
-      let(:group_milestone) { create(:milestone, group: group) }
-      let(:group_service) { described_class.new(group, user, {}) }
-
-      it 'does not execute hooks for group milestones' do
-        allow(group_milestone).to receive(:project_milestone?).and_return(false)
 
-        expect(group).not_to receive(:execute_hooks)
+      context 'when milestone is a group milestone' do
+        let(:group) { create(:group) }
+        let(:milestone) { create(:milestone, group: group) }
 
-        group_service.send(:execute_hooks, group_milestone, 'close')
+        it_behaves_like 'does not close the milestone'
       end
     end
   end
diff --git a/spec/services/milestones/create_service_spec.rb b/spec/services/milestones/create_service_spec.rb
index 2f8c1df09a587e..1999b1d40392bb 100644
--- a/spec/services/milestones/create_service_spec.rb
+++ b/spec/services/milestones/create_service_spec.rb
@@ -30,10 +30,27 @@
         expect(milestone.description).to eq('Description')
       end
 
-      it 'executes hooks with create action and creates new event' do
-        expect(create_milestone).to receive(:execute_hooks).with(kind_of(Milestone), 'create')
+      shared_examples 'creates the milestone' do |with_project_hooks:|
+        it 'executes hooks with create action and creates new event' do
+          expect(create_milestone).to receive(:execute_hooks).with(kind_of(Milestone), 'create').and_call_original
+          expect(project).to receive(:execute_hooks).with(kind_of(Hash), :milestone_hooks) if with_project_hooks
 
-        expect { create_milestone.execute }.to change { Event.count }.by(1)
+          expect { create_milestone.execute }.to change { Event.count }.by(1)
+        end
+      end
+
+      context 'when project has active milestone hooks' do
+        let(:project) do
+          create(:project).tap do |project|
+            create(:project_hook, project: project, milestone_events: true)
+          end
+        end
+
+        it_behaves_like 'creates the milestone', with_project_hooks: true
+      end
+
+      context 'when project has no active milestone hooks' do
+        it_behaves_like 'creates the milestone', with_project_hooks: false
       end
     end
 
@@ -68,62 +85,25 @@
       end
     end
 
-    it 'calls before_create method' do
-      expect(create_milestone).to receive(:before_create)
-      create_milestone.execute
-    end
-  end
-
-  describe 'webhook execution' do
-    let(:milestone) { create(:milestone, project: project) }
-
-    context 'when project has active milestone hooks' do
-      before do
-        create(:project_hook, project: project, milestone_events: true)
-      end
-
-      it 'executes milestone hooks with correct payload when conditions are met' do
-        allow(milestone).to receive(:project_milestone?).and_return(true)
-        allow(project).to receive(:has_active_hooks?).with(:milestone_hooks).and_return(true)
-        expected_payload = Gitlab::DataBuilder::Milestone.build(milestone, 'create')
-
-        expect(project).to receive(:execute_hooks).with(expected_payload, :milestone_hooks)
-
-        create_milestone.send(:execute_hooks, milestone, 'create')
-      end
-
-      it 'only executes active hooks for project milestones' do
-        allow(milestone).to receive(:project_milestone?).and_return(true)
-
-        expect(project).to receive(:has_active_hooks?).with(:milestone_hooks).and_return(true)
-        expect(project).to receive(:execute_hooks)
-
-        create_milestone.send(:execute_hooks, milestone, 'create')
-      end
-    end
-
-    context 'when project has no active milestone hooks' do
-      it 'does not execute hooks when no active hooks' do
-        allow(milestone).to receive(:project_milestone?).and_return(true)
-        allow(project).to receive(:has_active_hooks?).with(:milestone_hooks).and_return(false)
-
-        expect(project).not_to receive(:execute_hooks)
-
-        create_milestone.send(:execute_hooks, milestone, 'create')
-      end
-    end
-
     context 'when milestone is a group milestone' do
       let(:group) { create(:group) }
-      let(:group_milestone) { create(:milestone, group: group) }
       let(:group_service) { described_class.new(group, user, params) }
 
       it 'does not execute hooks for group milestones' do
+        milestone = build(:milestone, group: group)
+        allow(milestone).to receive(:save).and_return(true)
+        allow(group_service).to receive(:build_milestone).and_return(milestone)
+
         expect(group).not_to receive(:execute_hooks)
 
-        group_service.send(:execute_hooks, group_milestone, 'create')
+        group_service.execute
       end
     end
+
+    it 'calls before_create method' do
+      expect(create_milestone).to receive(:before_create)
+      create_milestone.execute
+    end
   end
 
   describe '#before_create' do
diff --git a/spec/services/milestones/reopen_service_spec.rb b/spec/services/milestones/reopen_service_spec.rb
index 199ad404bc7a8f..fc7874cbc84fb5 100644
--- a/spec/services/milestones/reopen_service_spec.rb
+++ b/spec/services/milestones/reopen_service_spec.rb
@@ -15,91 +15,70 @@
   describe '#execute' do
     let(:service) { described_class.new(project, user, {}) }
 
-    before do
-      service.execute(milestone)
-    end
+    context 'when service is called before test suite' do
+      before do
+        service.execute(milestone)
+      end
 
-    it { expect(milestone).to be_valid }
-    it { expect(milestone).to be_active }
+      it { expect(milestone).to be_valid }
+      it { expect(milestone).to be_active }
 
-    describe 'event' do
-      let(:event) { Event.recent.first }
+      describe 'event' do
+        let(:event) { Event.recent.first }
 
-      it { expect(event.milestone).to be_truthy }
-      it { expect(event.target).to eq(milestone) }
-      it { expect(event.action_name).to eq('opened') }
+        it { expect(event.milestone).to be_truthy }
+        it { expect(event.target).to eq(milestone) }
+        it { expect(event.action_name).to eq('opened') }
+      end
     end
 
-    context 'when milestone is successfully reopened' do
+    shared_examples 'reopens the milestone' do |with_project_hooks:|
       it 'executes hooks with reopen action and creates new event' do
-        closed_milestone = create(:milestone, :closed, project: project)
-
-        expect(service).to receive(:execute_hooks).with(closed_milestone, 'reopen')
+        expect(service).to receive(:execute_hooks).with(milestone, 'reopen').and_call_original
+        expect(project).to receive(:execute_hooks).with(kind_of(Hash), :milestone_hooks) if with_project_hooks
 
-        expect { service.execute(closed_milestone) }.to change { Event.count }.by(1)
+        expect { service.execute(milestone) }.to change { Event.count }.by(1)
       end
     end
 
-    context 'when milestone fails to reopen' do
+    shared_examples 'does not reopen the milestone' do
       it 'does not execute hooks and does not create new event' do
-        active_milestone = create(:milestone, project: project)
-
         expect(service).not_to receive(:execute_hooks)
 
-        expect { service.execute(active_milestone) }.not_to change { Event.count }
+        expect { service.execute(milestone) }.not_to change { Event.count }
       end
     end
-  end
-
-  describe 'webhook execution' do
-    let(:service) { described_class.new(project, user, {}) }
 
-    context 'when project has active milestone hooks' do
-      before do
-        create(:project_hook, project: project, milestone_events: true)
-      end
-
-      it 'executes milestone hooks with correct payload when conditions are met' do
-        allow(milestone).to receive(:project_milestone?).and_return(true)
-        allow(project).to receive(:has_active_hooks?).with(:milestone_hooks).and_return(true)
-        expected_payload = Gitlab::DataBuilder::Milestone.build(milestone, 'reopen')
+    context 'when milestone is successfully reopened' do
+      let(:milestone) { create(:milestone, :closed, project: project) }
 
-        expect(project).to receive(:execute_hooks).with(expected_payload, :milestone_hooks)
+      context 'when project has active milestone hooks' do
+        let(:project) do
+          create(:project).tap do |project|
+            create(:project_hook, project: project, milestone_events: true)
+          end
+        end
 
-        service.send(:execute_hooks, milestone, 'reopen')
+        it_behaves_like 'reopens the milestone', with_project_hooks: true
       end
 
-      it 'only executes hooks for project milestones' do
-        allow(milestone).to receive(:project_milestone?).and_return(true)
-        expect(project).to receive(:has_active_hooks?).with(:milestone_hooks).and_return(true)
-        expect(project).to receive(:execute_hooks)
-
-        service.send(:execute_hooks, milestone, 'reopen')
+      context 'when project has no active milestone hooks' do
+        it_behaves_like 'reopens the milestone', with_project_hooks: false
       end
     end
 
-    context 'when project has no active milestone hooks' do
-      it 'does not execute hooks when no active hooks' do
-        allow(milestone).to receive(:project_milestone?).and_return(true)
-        allow(project).to receive(:has_active_hooks?).with(:milestone_hooks).and_return(false)
-
-        expect(project).not_to receive(:execute_hooks)
+    context 'when milestone fails to reopen' do
+      context 'when milestone is already active' do
+        let(:milestone) { create(:milestone, project: project) }
 
-        service.send(:execute_hooks, milestone, 'reopen')
+        it_behaves_like 'does not reopen the milestone'
       end
-    end
-
-    context 'when milestone is a group milestone' do
-      let(:group) { create(:group) }
-      let(:group_milestone) { create(:milestone, :closed, group: group) }
-      let(:group_service) { described_class.new(group, user, {}) }
-
-      it 'does not execute hooks for group milestones' do
-        allow(group_milestone).to receive(:project_milestone?).and_return(false)
 
-        expect(group).not_to receive(:execute_hooks)
+      context 'when milestone is a group milestone' do
+        let(:group) { create(:group) }
+        let(:milestone) { create(:milestone, :closed, group: group) }
 
-        group_service.send(:execute_hooks, group_milestone, 'reopen')
+        it_behaves_like 'does not reopen the milestone'
       end
     end
   end
-- 
GitLab


From 7ed2e400a49a43f52b2cf94c4e8437d3d38dc32d Mon Sep 17 00:00:00 2001
From: Alex Kozenko <9867893@gmail.com>
Date: Wed, 25 Jun 2025 12:41:07 +0300
Subject: [PATCH 11/15] Add on-delete milestone-webhook

---
 app/services/milestones/destroy_service.rb       | 1 +
 app/views/shared/web_hooks/_form.html.haml       | 2 +-
 doc/user/project/integrations/webhook_events.md  | 4 ++--
 locale/gitlab.pot                                | 2 +-
 spec/services/milestones/destroy_service_spec.rb | 8 ++++++--
 5 files changed, 11 insertions(+), 6 deletions(-)

diff --git a/app/services/milestones/destroy_service.rb b/app/services/milestones/destroy_service.rb
index 6966764634f1ec..dc605472e37bf0 100644
--- a/app/services/milestones/destroy_service.rb
+++ b/app/services/milestones/destroy_service.rb
@@ -14,6 +14,7 @@ def execute(milestone)
 
       return unless milestone.destroyed?
 
+      execute_hooks(milestone, 'delete') if milestone.project_milestone?
       milestone
     end
 
diff --git a/app/views/shared/web_hooks/_form.html.haml b/app/views/shared/web_hooks/_form.html.haml
index 7c7a60adcc829b..e8106aa9c6fb09 100644
--- a/app/views/shared/web_hooks/_form.html.haml
+++ b/app/views/shared/web_hooks/_form.html.haml
@@ -61,7 +61,7 @@
     %li.gl-pb-3
       = form.gitlab_ui_checkbox_component :milestone_events,
           integration_webhook_event_human_name(:milestone_events),
-          help_text: s_('Webhooks|A milestone is created, closed, or reopened.')
+          help_text: s_('Webhooks|A milestone is created, closed, reopened or deleted.')
     %li.gl-pb-3
       - emoji_help_link = link_to s_('Which emoji events trigger webhooks'), help_page_path('user/project/integrations/webhook_events.md', anchor: 'emoji-events')
       = form.gitlab_ui_checkbox_component :emoji_events,
diff --git a/doc/user/project/integrations/webhook_events.md b/doc/user/project/integrations/webhook_events.md
index febda63c8a6e23..fe613dcefcd9f1 100644
--- a/doc/user/project/integrations/webhook_events.md
+++ b/doc/user/project/integrations/webhook_events.md
@@ -37,7 +37,7 @@ Event type                                   | Trigger
 [Deployment event](#deployment-events)       | A deployment starts, succeeds, fails, or is canceled.
 [Feature flag event](#feature-flag-events)   | A feature flag is turned on or off.
 [Release event](#release-events)             | A release is created, edited, or deleted.
-[Milestone event](#milestone-events)         | A milestone is created, closed, or reopened.
+[Milestone event](#milestone-events)         | A milestone is created, closed, reopened or deleted.
 [Emoji event](#emoji-events)                 | An emoji reaction is added or removed.
 [Project or group access token event](#project-and-group-access-token-events) | A project or group access token will expire in seven days.
 [Vulnerability event](#vulnerability-events) | A vulnerability is created or updated.
@@ -2140,7 +2140,7 @@ Payload example:
 
 ## Milestone events
 
-Milestone events are triggered when a milestone is created, closed, or reopened.
+Milestone events are triggered when a milestone is created, closed, reopened, or deleted.
 
 The available values for `object_attributes.action` in the payload are:
 
diff --git a/locale/gitlab.pot b/locale/gitlab.pot
index 80e837e30b18b5..620af8c2ba80f3 100644
--- a/locale/gitlab.pot
+++ b/locale/gitlab.pot
@@ -69166,7 +69166,7 @@ msgstr ""
 msgid "Webhooks|A merge request is created, updated, or merged."
 msgstr ""
 
-msgid "Webhooks|A milestone is created, closed, or reopened."
+msgid "Webhooks|A milestone is created, closed, reopened or deleted."
 msgstr ""
 
 msgid "Webhooks|A new tag is pushed to the repository."
diff --git a/spec/services/milestones/destroy_service_spec.rb b/spec/services/milestones/destroy_service_spec.rb
index fd276a54e10111..c76edd2648c361 100644
--- a/spec/services/milestones/destroy_service_spec.rb
+++ b/spec/services/milestones/destroy_service_spec.rb
@@ -48,7 +48,9 @@
 
       it_behaves_like 'deletes milestone id from issuables'
 
-      it 'logs destroy event' do
+      it 'logs destroy event and runs on-delete webhook' do
+        expect(service).to receive(:execute_hooks).with(milestone, 'delete')
+
         service.execute(milestone)
 
         event = Event.where(project_id: milestone.project_id, target_type: 'Milestone')
@@ -84,7 +86,9 @@
 
       it_behaves_like 'deletes milestone id from issuables'
 
-      it 'does not log destroy event' do
+      it 'does not log destroy event and does not run on-delete webhook' do
+        expect(service).not_to receive(:execute_hooks).with(milestone, 'delete')
+
         expect { service.execute(milestone) }.not_to change { Event.count }
       end
     end
-- 
GitLab


From ab989770a1160ba1bf60989844212b6a067a7859 Mon Sep 17 00:00:00 2001
From: Alex Kozenko <9867893@gmail.com>
Date: Thu, 26 Jun 2025 12:52:05 +0300
Subject: [PATCH 12/15] Add test case for milestone-event to the
 Integrations::Test::ProjectService specs

---
 spec/services/integrations/test/project_service_spec.rb | 9 +++++++++
 1 file changed, 9 insertions(+)

diff --git a/spec/services/integrations/test/project_service_spec.rb b/spec/services/integrations/test/project_service_spec.rb
index 4f8f932fb45c76..b23e0671e49eb6 100644
--- a/spec/services/integrations/test/project_service_spec.rb
+++ b/spec/services/integrations/test/project_service_spec.rb
@@ -41,6 +41,15 @@
         end
       end
 
+      context 'milestone' do
+        let(:event) { 'milestone' }
+
+        it 'returns error message that testing is not available for this event' do
+          expect(integration).not_to receive(:test)
+          expect(subject).to include({ status: :error, message: 'Testing not available for this event' })
+        end
+      end
+
       context 'push' do
         let(:event) { 'push' }
 
-- 
GitLab


From 48f4472e8495ba220e60b69e493c94782667cfbf Mon Sep 17 00:00:00 2001
From: Alex Kozenko <9867893@gmail.com>
Date: Fri, 27 Jun 2025 10:30:48 +0300
Subject: [PATCH 13/15] Update documentation for milestone webhook

---
 app/views/shared/web_hooks/_form.html.haml      | 2 +-
 doc/user/project/integrations/webhook_events.md | 8 +++++++-
 locale/gitlab.pot                               | 2 +-
 3 files changed, 9 insertions(+), 3 deletions(-)

diff --git a/app/views/shared/web_hooks/_form.html.haml b/app/views/shared/web_hooks/_form.html.haml
index e8106aa9c6fb09..3be7461410d8bb 100644
--- a/app/views/shared/web_hooks/_form.html.haml
+++ b/app/views/shared/web_hooks/_form.html.haml
@@ -61,7 +61,7 @@
     %li.gl-pb-3
       = form.gitlab_ui_checkbox_component :milestone_events,
           integration_webhook_event_human_name(:milestone_events),
-          help_text: s_('Webhooks|A milestone is created, closed, reopened or deleted.')
+          help_text: s_('Webhooks|A milestone is created, closed, reopened, or deleted.')
     %li.gl-pb-3
       - emoji_help_link = link_to s_('Which emoji events trigger webhooks'), help_page_path('user/project/integrations/webhook_events.md', anchor: 'emoji-events')
       = form.gitlab_ui_checkbox_component :emoji_events,
diff --git a/doc/user/project/integrations/webhook_events.md b/doc/user/project/integrations/webhook_events.md
index fe613dcefcd9f1..a32c9ed85a79eb 100644
--- a/doc/user/project/integrations/webhook_events.md
+++ b/doc/user/project/integrations/webhook_events.md
@@ -37,7 +37,7 @@ Event type                                   | Trigger
 [Deployment event](#deployment-events)       | A deployment starts, succeeds, fails, or is canceled.
 [Feature flag event](#feature-flag-events)   | A feature flag is turned on or off.
 [Release event](#release-events)             | A release is created, edited, or deleted.
-[Milestone event](#milestone-events)         | A milestone is created, closed, reopened or deleted.
+[Milestone event](#milestone-events)         | A milestone is created, closed, reopened, or deleted.
 [Emoji event](#emoji-events)                 | An emoji reaction is added or removed.
 [Project or group access token event](#project-and-group-access-token-events) | A project or group access token will expire in seven days.
 [Vulnerability event](#vulnerability-events) | A vulnerability is created or updated.
@@ -2140,6 +2140,12 @@ Payload example:
 
 ## Milestone events
 
+{{< history >}}
+
+- [Introduced](https://gitlab.com/gitlab-org/gitlab/-/issues/14213) in GitLab 18.2.
+
+{{< /history >}}
+
 Milestone events are triggered when a milestone is created, closed, reopened, or deleted.
 
 The available values for `object_attributes.action` in the payload are:
diff --git a/locale/gitlab.pot b/locale/gitlab.pot
index 9aadd8084ee7f0..d4f32edb27034f 100644
--- a/locale/gitlab.pot
+++ b/locale/gitlab.pot
@@ -69269,7 +69269,7 @@ msgstr ""
 msgid "Webhooks|A merge request is created, updated, or merged."
 msgstr ""
 
-msgid "Webhooks|A milestone is created, closed, reopened or deleted."
+msgid "Webhooks|A milestone is created, closed, reopened, or deleted."
 msgstr ""
 
 msgid "Webhooks|A new tag is pushed to the repository."
-- 
GitLab


From 2f81dfe0a6197baaec7704b2f5a4eb3f0a9cd4db Mon Sep 17 00:00:00 2001
From: Alex Kozenko <9867893@gmail.com>
Date: Mon, 30 Jun 2025 15:21:06 +0300
Subject: [PATCH 14/15] Modify spec for milestone-webhook integrations

---
 .../integrations/test/project_service_spec.rb     | 15 ++++++++++++---
 1 file changed, 12 insertions(+), 3 deletions(-)

diff --git a/spec/services/integrations/test/project_service_spec.rb b/spec/services/integrations/test/project_service_spec.rb
index b23e0671e49eb6..cc88a815f65b45 100644
--- a/spec/services/integrations/test/project_service_spec.rb
+++ b/spec/services/integrations/test/project_service_spec.rb
@@ -44,9 +44,18 @@
       context 'milestone' do
         let(:event) { 'milestone' }
 
-        it 'returns error message that testing is not available for this event' do
-          expect(integration).not_to receive(:test)
-          expect(subject).to include({ status: :error, message: 'Testing not available for this event' })
+        before do
+          # Mock the integration to support milestone events for testing
+          allow(integration).to receive(:supported_events).and_return(integration.supported_events + ['milestone'])
+        end
+
+        it 'executes integration' do
+          milestone = create(:milestone, project: project)
+          allow(Gitlab::DataBuilder::Milestone).to receive(:build).and_return(sample_data)
+          allow_next(MilestonesFinder).to receive(:execute).and_return([milestone])
+
+          expect(integration).to receive(:test).with(sample_data).and_return(success_result)
+          expect(subject).to eq(success_result)
         end
       end
 
-- 
GitLab


From 0556f54017414514d15b4317d756e5e7b58776fb Mon Sep 17 00:00:00 2001
From: Alex Kozenko <9867893@gmail.com>
Date: Tue, 1 Jul 2025 12:52:54 +0300
Subject: [PATCH 15/15] Remove redundunt rubocop:enable instruction

---
 app/services/integrations/test/project_service.rb | 2 +-
 1 file changed, 1 insertion(+), 1 deletion(-)

diff --git a/app/services/integrations/test/project_service.rb b/app/services/integrations/test/project_service.rb
index ddba08e388231d..3334b241dddae6 100644
--- a/app/services/integrations/test/project_service.rb
+++ b/app/services/integrations/test/project_service.rb
@@ -43,7 +43,7 @@ def data # rubocop:disable Metrics/CyclomaticComplexity -- despite a high count
             current_user_events_data
           end
         end
-      end # rubocop:enable Metrics/CyclomaticComplexity
+      end
     end
   end
 end
-- 
GitLab