diff --git a/Gemfile b/Gemfile
index 57853f9f3b5..ad75d89221f 100644
--- a/Gemfile
+++ b/Gemfile
@@ -25,7 +25,9 @@ gem 'faraday', '~> 1.0'
 gem 'marginalia', '~> 1.9.0'
 
 # Authentication libraries
-gem 'devise', '~> 4.6'
+gem 'devise', '~> 4.7.2'
+# TODO: verify ARM compile issue on 3.1.13+ version (see https://gitlab.com/gitlab-org/gitlab/-/merge_requests/18828)
+gem 'bcrypt', '3.1.12'
 gem 'doorkeeper', '~> 5.3.0'
 gem 'doorkeeper-openid_connect', '~> 1.7.4'
 gem 'omniauth', '~> 1.8'
@@ -120,7 +122,7 @@ gem 'fog-local', '~> 0.6'
 gem 'fog-openstack', '~> 1.0'
 gem 'fog-rackspace', '~> 0.1.1'
 gem 'fog-aliyun', '~> 0.3'
-gem 'gitlab-fog-azure-rm', '~> 0.9', require: false
+gem 'gitlab-fog-azure-rm', '~> 1.0', require: false
 
 # for Google storage
 gem 'google-api-client', '~> 0.33'
diff --git a/Gemfile.lock b/Gemfile.lock
index 142a606faa0..9238920c78c 100644
--- a/Gemfile.lock
+++ b/Gemfile.lock
@@ -235,7 +235,7 @@ GEM
       thor (>= 0.19, < 2)
       unicode_plot (>= 0.0.4, < 1.0.0)
     device_detector (1.0.0)
-    devise (4.7.1)
+    devise (4.7.3)
       bcrypt (~> 3.0)
       orm_adapter (~> 0.1)
       railties (>= 4.1.0)
@@ -421,7 +421,7 @@ GEM
     github-markup (1.7.0)
     gitlab-chronic (0.10.5)
       numerizer (~> 0.2)
-    gitlab-fog-azure-rm (0.9.0)
+    gitlab-fog-azure-rm (1.0.0)
       azure-storage-blob (~> 2.0)
       azure-storage-common (~> 2.0)
       fog-core (= 2.1.0)
@@ -1257,6 +1257,7 @@ DEPENDENCIES
   babosa (~> 1.0.2)
   base32 (~> 0.3.0)
   batch-loader (~> 1.4.0)
+  bcrypt (= 3.1.12)
   bcrypt_pbkdf (~> 1.0)
   benchmark-ips (~> 2.3.0)
   benchmark-memory (~> 0.1)
@@ -1282,7 +1283,7 @@ DEPENDENCIES
   default_value_for (~> 3.3.0)
   derailed_benchmarks
   device_detector
-  devise (~> 4.6)
+  devise (~> 4.7.2)
   devise-two-factor (~> 3.1.0)
   diff_match_patch (~> 0.1.0)
   diffy (~> 3.3)
@@ -1323,7 +1324,7 @@ DEPENDENCIES
   gitaly (~> 13.3.0.pre.rc1)
   github-markup (~> 1.7.0)
   gitlab-chronic (~> 0.10.5)
-  gitlab-fog-azure-rm (~> 0.9)
+  gitlab-fog-azure-rm (~> 1.0)
   gitlab-labkit (= 0.12.1)
   gitlab-license (~> 1.0)
   gitlab-mail_room (~> 0.0.6)
diff --git a/app/helpers/services_helper.rb b/app/helpers/services_helper.rb
index ae59f84e7da..114bbf59ae1 100644
--- a/app/helpers/services_helper.rb
+++ b/app/helpers/services_helper.rb
@@ -24,7 +24,7 @@ module ServicesHelper
     when "commit", "commit_events"
       s_("ProjectService|Event will be triggered when a commit is created/updated")
     when "deployment"
-      s_("ProjectService|Event will be triggered when a deployment finishes")
+      s_("ProjectService|Event will be triggered when a deployment starts or finishes")
     when "alert"
       s_("ProjectService|Event will be triggered when a new, unique alert is recorded")
     end
diff --git a/app/models/deployment.rb b/app/models/deployment.rb
index 3978620c74d..bc4a23bfb68 100644
--- a/app/models/deployment.rb
+++ b/app/models/deployment.rb
@@ -46,6 +46,8 @@ class Deployment < ApplicationRecord
   scope :older_than, -> (deployment) { where('id < ?', deployment.id) }
   scope :with_deployable, -> { includes(:deployable).where('deployable_id IS NOT NULL') }
 
+  FINISHED_STATUSES = %i[success failed canceled].freeze
+
   state_machine :status, initial: :created do
     event :run do
       transition created: :running
@@ -63,22 +65,10 @@ class Deployment < ApplicationRecord
       transition any - [:canceled] => :canceled
     end
 
-    before_transition any => [:success, :failed, :canceled] do |deployment|
+    before_transition any => FINISHED_STATUSES do |deployment|
       deployment.finished_at = Time.current
     end
 
-    after_transition any => :success do |deployment|
-      deployment.run_after_commit do
-        Deployments::SuccessWorker.perform_async(id)
-      end
-    end
-
-    after_transition any => [:success, :failed, :canceled] do |deployment|
-      deployment.run_after_commit do
-        Deployments::FinishedWorker.perform_async(id)
-      end
-    end
-
     after_transition any => :running do |deployment|
       next unless deployment.project.forward_deployment_enabled?
 
@@ -86,6 +76,32 @@ class Deployment < ApplicationRecord
         Deployments::ForwardDeploymentWorker.perform_async(id)
       end
     end
+
+    after_transition any => :running do |deployment|
+      deployment.run_after_commit do
+        next unless Feature.enabled?(:ci_send_deployment_hook_when_start, deployment.project)
+
+        Deployments::ExecuteHooksWorker.perform_async(id)
+      end
+    end
+
+    after_transition any => :success do |deployment|
+      deployment.run_after_commit do
+        Deployments::UpdateEnvironmentWorker.perform_async(id)
+      end
+    end
+
+    after_transition any => FINISHED_STATUSES do |deployment|
+      deployment.run_after_commit do
+        Deployments::LinkMergeRequestWorker.perform_async(id)
+      end
+    end
+
+    after_transition any => FINISHED_STATUSES do |deployment|
+      deployment.run_after_commit do
+        Deployments::ExecuteHooksWorker.perform_async(id)
+      end
+    end
   end
 
   enum status: {
@@ -273,7 +289,7 @@ class Deployment < ApplicationRecord
     SQL
   end
 
-  # Changes the status of a deployment and triggers the correspinding state
+  # Changes the status of a deployment and triggers the corresponding state
   # machine events.
   def update_status(status)
     case status
diff --git a/app/models/project_services/chat_message/deployment_message.rb b/app/models/project_services/chat_message/deployment_message.rb
index dae3a56116e..5deb757e60f 100644
--- a/app/models/project_services/chat_message/deployment_message.rb
+++ b/app/models/project_services/chat_message/deployment_message.rb
@@ -38,7 +38,11 @@ module ChatMessage
     private
 
     def message
-      "Deploy to #{environment} #{humanized_status}"
+      if running?
+        "Starting deploy to #{environment}"
+      else
+        "Deploy to #{environment} #{humanized_status}"
+      end
     end
 
     def color
@@ -73,5 +77,9 @@ module ChatMessage
     def humanized_status
       status == 'success' ? 'succeeded' : status
     end
+
+    def running?
+      status == 'running'
+    end
   end
 end
diff --git a/app/services/deployments/after_create_service.rb b/app/services/deployments/update_environment_service.rb
similarity index 91%
rename from app/services/deployments/after_create_service.rb
rename to app/services/deployments/update_environment_service.rb
index 3560f9c983b..e9c2f41f626 100644
--- a/app/services/deployments/after_create_service.rb
+++ b/app/services/deployments/update_environment_service.rb
@@ -1,7 +1,7 @@
 # frozen_string_literal: true
 
 module Deployments
-  class AfterCreateService
+  class UpdateEnvironmentService
     attr_reader :deployment
     attr_reader :deployable
 
@@ -64,4 +64,4 @@ module Deployments
   end
 end
 
-Deployments::AfterCreateService.prepend_if_ee('EE::Deployments::AfterCreateService')
+Deployments::UpdateEnvironmentService.prepend_if_ee('EE::Deployments::UpdateEnvironmentService')
diff --git a/app/views/shared/web_hooks/_form.html.haml b/app/views/shared/web_hooks/_form.html.haml
index 96da5136908..9c60201412c 100644
--- a/app/views/shared/web_hooks/_form.html.haml
+++ b/app/views/shared/web_hooks/_form.html.haml
@@ -77,7 +77,7 @@
       = form.label :deployment_events, class: 'list-label form-check-label ml-1' do
         %strong= s_('Webhooks|Deployment events')
       %p.text-muted.ml-1
-        = s_('Webhooks|This URL will be triggered when a deployment is finished/failed/canceled')
+        = s_('Webhooks|This URL is triggered when a deployment starts, finishes, fails, or is canceled')
 .form-group
   = form.label :enable_ssl_verification, s_('Webhooks|SSL verification'), class: 'label-bold checkbox'
   .form-check
diff --git a/app/workers/all_queues.yml b/app/workers/all_queues.yml
index bdcb31b8d46..4b2d32b47d3 100644
--- a/app/workers/all_queues.yml
+++ b/app/workers/all_queues.yml
@@ -427,6 +427,14 @@
   :weight: 1
   :idempotent: true
   :tags: []
+- :name: deployment:deployments_execute_hooks
+  :feature_category: :continuous_delivery
+  :has_external_dependencies:
+  :urgency: :low
+  :resource_boundary: :cpu
+  :weight: 3
+  :idempotent:
+  :tags: []
 - :name: deployment:deployments_finished
   :feature_category: :continuous_delivery
   :has_external_dependencies:
@@ -443,6 +451,14 @@
   :weight: 3
   :idempotent:
   :tags: []
+- :name: deployment:deployments_link_merge_request
+  :feature_category: :continuous_delivery
+  :has_external_dependencies:
+  :urgency: :low
+  :resource_boundary: :cpu
+  :weight: 3
+  :idempotent: true
+  :tags: []
 - :name: deployment:deployments_success
   :feature_category: :continuous_delivery
   :has_external_dependencies:
@@ -451,6 +467,14 @@
   :weight: 3
   :idempotent:
   :tags: []
+- :name: deployment:deployments_update_environment
+  :feature_category: :continuous_delivery
+  :has_external_dependencies:
+  :urgency: :low
+  :resource_boundary: :cpu
+  :weight: 3
+  :idempotent: true
+  :tags: []
 - :name: gcp_cluster:cluster_configure_istio
   :feature_category: :kubernetes_management
   :has_external_dependencies: true
diff --git a/app/workers/deployments/execute_hooks_worker.rb b/app/workers/deployments/execute_hooks_worker.rb
new file mode 100644
index 00000000000..6be05232321
--- /dev/null
+++ b/app/workers/deployments/execute_hooks_worker.rb
@@ -0,0 +1,17 @@
+# frozen_string_literal: true
+
+module Deployments
+  class ExecuteHooksWorker # rubocop:disable Scalability/IdempotentWorker
+    include ApplicationWorker
+
+    queue_namespace :deployment
+    feature_category :continuous_delivery
+    worker_resource_boundary :cpu
+
+    def perform(deployment_id)
+      if (deploy = Deployment.find_by_id(deployment_id))
+        deploy.execute_hooks
+      end
+    end
+  end
+end
diff --git a/app/workers/deployments/link_merge_request_worker.rb b/app/workers/deployments/link_merge_request_worker.rb
new file mode 100644
index 00000000000..4723691a0bb
--- /dev/null
+++ b/app/workers/deployments/link_merge_request_worker.rb
@@ -0,0 +1,18 @@
+# frozen_string_literal: true
+
+module Deployments
+  class LinkMergeRequestWorker
+    include ApplicationWorker
+
+    queue_namespace :deployment
+    idempotent!
+    feature_category :continuous_delivery
+    worker_resource_boundary :cpu
+
+    def perform(deployment_id)
+      if (deploy = Deployment.find_by_id(deployment_id))
+        LinkMergeRequestsService.new(deploy).execute
+      end
+    end
+  end
+end
diff --git a/app/workers/deployments/success_worker.rb b/app/workers/deployments/success_worker.rb
index 17f790d2f6f..ff1b2d80c1a 100644
--- a/app/workers/deployments/success_worker.rb
+++ b/app/workers/deployments/success_worker.rb
@@ -12,7 +12,7 @@ module Deployments
       Deployment.find_by_id(deployment_id).try do |deployment|
         break unless deployment.success?
 
-        Deployments::AfterCreateService.new(deployment).execute
+        Deployments::UpdateEnvironmentService.new(deployment).execute
       end
     end
   end
diff --git a/app/workers/deployments/update_environment_worker.rb b/app/workers/deployments/update_environment_worker.rb
new file mode 100644
index 00000000000..2381f9926bc
--- /dev/null
+++ b/app/workers/deployments/update_environment_worker.rb
@@ -0,0 +1,20 @@
+# frozen_string_literal: true
+
+module Deployments
+  class UpdateEnvironmentWorker
+    include ApplicationWorker
+
+    queue_namespace :deployment
+    idempotent!
+    feature_category :continuous_delivery
+    worker_resource_boundary :cpu
+
+    def perform(deployment_id)
+      Deployment.find_by_id(deployment_id).try do |deployment|
+        break unless deployment.success?
+
+        Deployments::UpdateEnvironmentService.new(deployment).execute
+      end
+    end
+  end
+end
diff --git a/changelogs/unreleased/send-chat-notification-when-deployment-starts.yml b/changelogs/unreleased/send-chat-notification-when-deployment-starts.yml
new file mode 100644
index 00000000000..d9330677a85
--- /dev/null
+++ b/changelogs/unreleased/send-chat-notification-when-deployment-starts.yml
@@ -0,0 +1,5 @@
+---
+title: Send chat notification when deployment starts
+merge_request: 41214
+author: Sashi Kumar
+type: added
diff --git a/changelogs/unreleased/sh-update-fog-azure-rm-gem.yml b/changelogs/unreleased/sh-update-fog-azure-rm-gem.yml
new file mode 100644
index 00000000000..25d143a011b
--- /dev/null
+++ b/changelogs/unreleased/sh-update-fog-azure-rm-gem.yml
@@ -0,0 +1,5 @@
+---
+title: Fix large backups not working with Azure Blob storage
+merge_request: 44233
+author:
+type: fixed
diff --git a/config/feature_flags/development/ci_send_deployment_hook_when_start.yml b/config/feature_flags/development/ci_send_deployment_hook_when_start.yml
new file mode 100644
index 00000000000..41f8e719b63
--- /dev/null
+++ b/config/feature_flags/development/ci_send_deployment_hook_when_start.yml
@@ -0,0 +1,7 @@
+---
+name: ci_send_deployment_hook_when_start
+introduced_by_url: https://gitlab.com/gitlab-org/gitlab/-/merge_requests/41214
+rollout_issue_url: https://gitlab.com/gitlab-org/gitlab/-/issues/247137
+group: group::progressive delivery
+type: development
+default_enabled: false
diff --git a/db/migrate/20200817195628_add_modified_to_approval_merge_request_rule.rb b/db/migrate/20200817195628_add_modified_to_approval_merge_request_rule.rb
new file mode 100644
index 00000000000..71a29ae9bc5
--- /dev/null
+++ b/db/migrate/20200817195628_add_modified_to_approval_merge_request_rule.rb
@@ -0,0 +1,9 @@
+# frozen_string_literal: true
+
+class AddModifiedToApprovalMergeRequestRule < ActiveRecord::Migration[6.0]
+  DOWNTIME = false
+
+  def change
+    add_column :approval_merge_request_rules, :modified_from_project_rule, :boolean, default: false, null: false
+  end
+end
diff --git a/db/post_migrate/20200901170135_backfill_modified_column_for_approval_merge_request_rules.rb b/db/post_migrate/20200901170135_backfill_modified_column_for_approval_merge_request_rules.rb
new file mode 100644
index 00000000000..9a9866f38ec
--- /dev/null
+++ b/db/post_migrate/20200901170135_backfill_modified_column_for_approval_merge_request_rules.rb
@@ -0,0 +1,17 @@
+# frozen_string_literal: true
+
+class BackfillModifiedColumnForApprovalMergeRequestRules < ActiveRecord::Migration[6.0]
+  include Gitlab::Database::Migrations::BackgroundMigrationHelpers
+
+  disable_ddl_transaction!
+
+  class ApprovalMergeRequestRule < ActiveRecord::Base
+    include ::EachBatch
+
+    self.table_name = 'approval_merge_request_rules'
+  end
+
+  def change
+    queue_background_migration_jobs_by_range_at_intervals(ApprovalMergeRequestRule, 'AddModifiedToApprovalMergeRequestRule', 2.minutes, batch_size: 10_000)
+  end
+end
diff --git a/db/schema_migrations/20200817195628 b/db/schema_migrations/20200817195628
new file mode 100644
index 00000000000..7d919242d89
--- /dev/null
+++ b/db/schema_migrations/20200817195628
@@ -0,0 +1 @@
+4da25ee40eabd81765b562929c819da1fc2b0f8afe1f4eefe6b769fcd8f0d4cd
\ No newline at end of file
diff --git a/db/schema_migrations/20200901170135 b/db/schema_migrations/20200901170135
new file mode 100644
index 00000000000..4f0f5213a98
--- /dev/null
+++ b/db/schema_migrations/20200901170135
@@ -0,0 +1 @@
+fca99780272ca4ceb42fd38d16f67cd4a0a675ecdaf91e51c4c0728205212ed0
\ No newline at end of file
diff --git a/db/structure.sql b/db/structure.sql
index 52369090416..bde64076670 100644
--- a/db/structure.sql
+++ b/db/structure.sql
@@ -9338,6 +9338,7 @@ CREATE TABLE approval_merge_request_rules (
     rule_type smallint DEFAULT 1 NOT NULL,
     report_type smallint,
     section text,
+    modified_from_project_rule boolean DEFAULT false NOT NULL,
     CONSTRAINT check_6fca5928b2 CHECK ((char_length(section) <= 255))
 );
 
diff --git a/doc/user/project/integrations/webhooks.md b/doc/user/project/integrations/webhooks.md
index 800eb1d3359..7adea5ebcd6 100644
--- a/doc/user/project/integrations/webhooks.md
+++ b/doc/user/project/integrations/webhooks.md
@@ -1303,7 +1303,12 @@ Note that `commit.id` is the ID of the pipeline, not the ID of the commit.
 
 ### Deployment events
 
-Triggered when deployment is finished/failed/canceled.
+Triggered when a deployment:
+
+- Starts ([Introduced](https://gitlab.com/gitlab-org/gitlab/-/merge_requests/41214) in GitLab 13.5.)
+- Succeeds
+- Fails
+- Is cancelled
 
 **Request Header**:
 
diff --git a/lib/gitlab/background_migration/add_modified_to_approval_merge_request_rule.rb b/lib/gitlab/background_migration/add_modified_to_approval_merge_request_rule.rb
new file mode 100644
index 00000000000..2148e96f6b4
--- /dev/null
+++ b/lib/gitlab/background_migration/add_modified_to_approval_merge_request_rule.rb
@@ -0,0 +1,73 @@
+# frozen_string_literal: true
+
+module Gitlab
+  module BackgroundMigration
+    # Compare all current rules to project rules
+    class AddModifiedToApprovalMergeRequestRule
+      # Stubbed class to access the Group table
+      class Group < ActiveRecord::Base
+        self.table_name = 'namespaces'
+        self.inheritance_column = :_type_disabled
+      end
+
+      # Stubbed class to access the ApprovalMergeRequestRule table
+      class ApprovalMergeRequestRule < ActiveRecord::Base
+        self.table_name = 'approval_merge_request_rules'
+
+        has_one :approval_merge_request_rule_source, class_name: 'AddModifiedToApprovalMergeRequestRule::ApprovalMergeRequestRuleSource'
+        has_one :approval_project_rule, through: :approval_merge_request_rule_source
+        has_and_belongs_to_many :groups,
+          class_name: 'AddModifiedToApprovalMergeRequestRule::Group', join_table: "#{self.table_name}_groups"
+      end
+
+      # Stubbed class to access the ApprovalProjectRule table
+      class ApprovalProjectRule < ActiveRecord::Base
+        self.table_name = 'approval_project_rules'
+
+        has_many :approval_merge_request_rule_sources, class_name: 'AddModifiedToApprovalMergeRequestRule::ApprovalMergeRequestRuleSource'
+        has_and_belongs_to_many :groups,
+          class_name: 'AddModifiedToApprovalMergeRequestRule::Group', join_table: "#{self.table_name}_groups"
+      end
+
+      # Stubbed class to access the ApprovalMergeRequestRuleSource table
+      class ApprovalMergeRequestRuleSource < ActiveRecord::Base
+        self.table_name = 'approval_merge_request_rule_sources'
+
+        belongs_to :approval_merge_request_rule, class_name: 'AddModifiedToApprovalMergeRequestRule::ApprovalMergeRequestRule'
+        belongs_to :approval_project_rule, class_name: 'AddModifiedToApprovalMergeRequestRule::ApprovalProjectRule'
+      end
+
+      def perform(start_id, stop_id)
+        approval_merge_requests_rules = ApprovalMergeRequestRule
+          .joins(:groups, :approval_merge_request_rule_source)
+          .where(id: start_id..stop_id)
+          .pluck(
+            'approval_merge_request_rule_sources.id as ars_id',
+            'approval_merge_request_rules_groups.id as amrg_id'
+          )
+
+        approval_project_rules = ApprovalProjectRule
+          .joins(:groups, approval_merge_request_rule_sources: :approval_merge_request_rule)
+          .where(approval_merge_request_rules: { id: start_id..stop_id })
+          .pluck(
+            'approval_merge_request_rule_sources.id as ars_id',
+            'approval_project_rules_groups.id as apg_id'
+          )
+
+        different_names_or_approval_sources = ApprovalMergeRequestRule.joins(:approval_project_rule, :approval_merge_request_rule_source)
+          .where(id: start_id..stop_id)
+          .where('approval_merge_request_rules.name != approval_project_rules.name OR ' \
+                'approval_merge_request_rules.approvals_required != approval_project_rules.approvals_required')
+          .pluck('approval_merge_request_rule_sources.id as ars_id')
+
+        intersected_set = approval_merge_requests_rules.to_set ^ approval_project_rules.to_set
+        source_ids = intersected_set.collect { |rule| rule[0] }.uniq
+
+        rule_sources = ApprovalMergeRequestRuleSource.where(id: source_ids + different_names_or_approval_sources)
+        changed_merge_request_rules = ApprovalMergeRequestRule.where(id: rule_sources.select(:approval_merge_request_rule_id))
+
+        changed_merge_request_rules.update_all(modified_from_project_rule: true)
+      end
+    end
+  end
+end
diff --git a/lib/gitlab/data_builder/deployment.rb b/lib/gitlab/data_builder/deployment.rb
index 70587b3132a..87ebe832862 100644
--- a/lib/gitlab/data_builder/deployment.rb
+++ b/lib/gitlab/data_builder/deployment.rb
@@ -20,8 +20,8 @@ module Gitlab
           environment: deployment.environment.name,
           project: deployment.project.hook_attrs,
           short_sha: deployment.short_sha,
-          user: deployment.user.hook_attrs,
-          user_url: Gitlab::UrlBuilder.build(deployment.user),
+          user: deployment.deployed_by.hook_attrs,
+          user_url: Gitlab::UrlBuilder.build(deployment.deployed_by),
           commit_url: Gitlab::UrlBuilder.build(deployment.commit),
           commit_title: deployment.commit.title
         }
diff --git a/locale/gitlab.pot b/locale/gitlab.pot
index d4048b717ff..8fdea2bcb15 100644
--- a/locale/gitlab.pot
+++ b/locale/gitlab.pot
@@ -20015,7 +20015,7 @@ msgstr ""
 msgid "ProjectService|Event will be triggered when a confidential issue is created/updated/closed"
 msgstr ""
 
-msgid "ProjectService|Event will be triggered when a deployment finishes"
+msgid "ProjectService|Event will be triggered when a deployment starts or finishes"
 msgstr ""
 
 msgid "ProjectService|Event will be triggered when a merge request is created/updated/merged"
@@ -28857,15 +28857,15 @@ msgstr ""
 msgid "Webhooks|Tag push events"
 msgstr ""
 
+msgid "Webhooks|This URL is triggered when a deployment starts, finishes, fails, or is canceled"
+msgstr ""
+
 msgid "Webhooks|This URL will be triggered by a push to the repository"
 msgstr ""
 
 msgid "Webhooks|This URL will be triggered when a confidential issue is created/updated/merged"
 msgstr ""
 
-msgid "Webhooks|This URL will be triggered when a deployment is finished/failed/canceled"
-msgstr ""
-
 msgid "Webhooks|This URL will be triggered when a merge request is created/updated/merged"
 msgstr ""
 
diff --git a/qa/Rakefile b/qa/Rakefile
index 844d8ff898d..1ecce8fdce9 100644
--- a/qa/Rakefile
+++ b/qa/Rakefile
@@ -2,6 +2,7 @@ require_relative 'qa/tools/revoke_all_personal_access_tokens'
 require_relative 'qa/tools/delete_subgroups'
 require_relative 'qa/tools/generate_perf_testdata'
 require_relative 'qa/tools/delete_test_ssh_keys'
+require_relative 'qa/tools/initialize_gitlab_auth'
 
 desc "Revokes all personal access tokens"
 task :revoke_personal_access_tokens do
@@ -13,6 +14,11 @@ task :delete_subgroups do
   QA::Tools::DeleteSubgroups.new.run
 end
 
+desc "Initialize GitLab with an access token"
+task :initialize_gitlab_auth, [:address] do |t, args|
+  QA::Tools::InitializeGitLabAuth.new(args).run
+end
+
 desc "Generate Performance Testdata"
 task :generate_perf_testdata, :type do |t, args|
   args.with_defaults(type: :all)
diff --git a/qa/qa/tools/initialize_gitlab_auth.rb b/qa/qa/tools/initialize_gitlab_auth.rb
new file mode 100644
index 00000000000..b06ddcab040
--- /dev/null
+++ b/qa/qa/tools/initialize_gitlab_auth.rb
@@ -0,0 +1,30 @@
+# frozen_string_literal: true
+
+require_relative '../../qa'
+
+module QA
+  module Tools
+    # Task to set default password from Runtime::Env.default_password if not set already
+    # Also creates a personal access token
+    # @example
+    #   $ bundle exec rake  'initialize_gitlab_auth[http://gitlab.test]'
+    class InitializeGitLabAuth
+      attr_reader :address
+
+      def initialize(address:)
+        @address = address
+      end
+
+      def run
+        Runtime::Scenario.define(:gitlab_address, address)
+
+        puts "Signing in and creating the default password for the root user if it's not set already..."
+        QA::Runtime::Browser.visit(:gitlab, QA::Page::Main::Login)
+        Flow::Login.sign_in
+
+        puts "Creating an API scoped access token for the root user..."
+        puts "Token: #{Resource::PersonalAccessToken.fabricate!.access_token}"
+      end
+    end
+  end
+end
diff --git a/spec/lib/gitlab/background_migration/add_modified_to_approval_merge_request_rule_spec.rb b/spec/lib/gitlab/background_migration/add_modified_to_approval_merge_request_rule_spec.rb
new file mode 100644
index 00000000000..81b8b5dde08
--- /dev/null
+++ b/spec/lib/gitlab/background_migration/add_modified_to_approval_merge_request_rule_spec.rb
@@ -0,0 +1,61 @@
+# frozen_string_literal: true
+
+require 'spec_helper'
+
+RSpec.describe Gitlab::BackgroundMigration::AddModifiedToApprovalMergeRequestRule, schema: 20200817195628 do
+  let(:determine_if_rules_are_modified) { described_class.new }
+
+  let(:namespace) { table(:namespaces).create!(name: 'gitlab', path: 'gitlab') }
+  let(:projects) { table(:projects) }
+  let(:normal_project) { projects.create!(namespace_id: namespace.id) }
+  let(:overridden_project) { projects.create!(namespace_id: namespace.id) }
+  let(:rules) { table(:approval_merge_request_rules) }
+  let(:project_rules) { table(:approval_project_rules) }
+  let(:sources) { table(:approval_merge_request_rule_sources) }
+  let(:merge_requests) { table(:merge_requests) }
+  let(:groups) { table(:namespaces) }
+  let(:mr_groups) { table(:approval_merge_request_rules_groups) }
+  let(:project_groups) { table(:approval_project_rules_groups) }
+
+  before do
+    project_rule = project_rules.create!(project_id: normal_project.id, approvals_required: 3, name: 'test rule')
+    overridden_project_rule = project_rules.create!(project_id: overridden_project.id, approvals_required: 5, name: 'other test rule')
+    overridden_project_rule_two = project_rules.create!(project_id: overridden_project.id, approvals_required: 7, name: 'super cool rule')
+
+    merge_request = merge_requests.create!(target_branch: 'feature', source_branch: 'default', source_project_id: normal_project.id, target_project_id: normal_project.id)
+    overridden_merge_request = merge_requests.create!(target_branch: 'feature-2', source_branch: 'default', source_project_id: overridden_project.id, target_project_id: overridden_project.id)
+
+    merge_rule = rules.create!(merge_request_id: merge_request.id, approvals_required: 3, name: 'test rule')
+    overridden_merge_rule = rules.create!(merge_request_id: overridden_merge_request.id, approvals_required: 6, name: 'other test rule')
+    overridden_merge_rule_two = rules.create!(merge_request_id: overridden_merge_request.id, approvals_required: 7, name: 'super cool rule')
+
+    sources.create!(approval_project_rule_id: project_rule.id, approval_merge_request_rule_id: merge_rule.id)
+    sources.create!(approval_project_rule_id: overridden_project_rule.id, approval_merge_request_rule_id: overridden_merge_rule.id)
+    sources.create!(approval_project_rule_id: overridden_project_rule_two.id, approval_merge_request_rule_id: overridden_merge_rule_two.id)
+
+    group1 = groups.create!(name: "group1", path: "test_group1", type: 'Group')
+    group2 = groups.create!(name: "group2", path: "test_group2", type: 'Group')
+    group3 = groups.create!(name: "group3", path: "test_group3", type: 'Group')
+
+    project_groups.create!(approval_project_rule_id: overridden_project_rule_two.id, group_id: group1.id)
+    project_groups.create!(approval_project_rule_id: overridden_project_rule_two.id, group_id: group2.id)
+    project_groups.create!(approval_project_rule_id: overridden_project_rule_two.id, group_id: group3.id)
+
+    mr_groups.create!(approval_merge_request_rule_id: overridden_merge_rule.id, group_id: group1.id)
+    mr_groups.create!(approval_merge_request_rule_id: overridden_merge_rule_two.id, group_id: group2.id)
+  end
+
+  describe '#perform' do
+    it 'changes the correct rules' do
+      original_count = rules.all.count
+
+      determine_if_rules_are_modified.perform(rules.minimum(:id), rules.maximum(:id))
+
+      results = rules.where(modified_from_project_rule: true)
+
+      expect(results.count).to eq 2
+      expect(results.collect(&:name)).to eq(['other test rule', 'super cool rule'])
+      expect(rules.count).to eq original_count
+    end
+  end
+end
diff --git a/spec/lib/gitlab/data_builder/deployment_spec.rb b/spec/lib/gitlab/data_builder/deployment_spec.rb
index 155e66e2fcd..8fb7ab25b17 100644
--- a/spec/lib/gitlab/data_builder/deployment_spec.rb
+++ b/spec/lib/gitlab/data_builder/deployment_spec.rb
@@ -19,7 +19,7 @@ RSpec.describe Gitlab::DataBuilder::Deployment do
       deployment = create(:deployment, status: :failed, environment: environment, sha: commit.sha, project: project)
       deployable = deployment.deployable
       expected_deployable_url = Gitlab::Routing.url_helpers.project_job_url(deployable.project, deployable)
-      expected_user_url = Gitlab::Routing.url_helpers.user_url(deployment.user)
+      expected_user_url = Gitlab::Routing.url_helpers.user_url(deployment.deployed_by)
       expected_commit_url = Gitlab::UrlBuilder.build(commit)
 
       data = described_class.build(deployment)
@@ -30,7 +30,7 @@ RSpec.describe Gitlab::DataBuilder::Deployment do
       expect(data[:environment]).to eq("somewhere")
       expect(data[:project]).to eq(project.hook_attrs)
       expect(data[:short_sha]).to eq(deployment.short_sha)
-      expect(data[:user]).to eq(deployment.user.hook_attrs)
+      expect(data[:user]).to eq(deployment.deployed_by.hook_attrs)
       expect(data[:user_url]).to eq(expected_user_url)
       expect(data[:commit_url]).to eq(expected_commit_url)
       expect(data[:commit_title]).to eq(commit.title)
diff --git a/spec/lib/gitlab/import_export/all_models.yml b/spec/lib/gitlab/import_export/all_models.yml
index 7c33f29ebf3..45f48cd8a57 100644
--- a/spec/lib/gitlab/import_export/all_models.yml
+++ b/spec/lib/gitlab/import_export/all_models.yml
@@ -159,6 +159,8 @@ merge_requests:
 - assignees
 - reviews
 - approval_rules
+- approval_merge_request_rule_sources
+- approval_project_rules
 - approvals
 - approvers
 - approver_users
@@ -467,6 +469,8 @@ project:
 - feature_usage
 - approval_rules
 - approval_merge_request_rules
+- approval_merge_request_rule_sources
+- approval_project_rules
 - approvers
 - approver_users
 - audit_events
diff --git a/spec/models/ci/build_spec.rb b/spec/models/ci/build_spec.rb
index cb29cbcbb72..49731757593 100644
--- a/spec/models/ci/build_spec.rb
+++ b/spec/models/ci/build_spec.rb
@@ -1109,7 +1109,8 @@ RSpec.describe Ci::Build do
     let(:environment) { deployment.environment }
 
     before do
-      allow(Deployments::FinishedWorker).to receive(:perform_async)
+      allow(Deployments::LinkMergeRequestWorker).to receive(:perform_async)
+      allow(Deployments::ExecuteHooksWorker).to receive(:perform_async)
     end
 
     it 'has deployments record with created status' do
@@ -1129,7 +1130,8 @@ RSpec.describe Ci::Build do
 
     context 'when transits to success' do
       before do
-        allow(Deployments::SuccessWorker).to receive(:perform_async)
+        allow(Deployments::UpdateEnvironmentWorker).to receive(:perform_async)
+        allow(Deployments::ExecuteHooksWorker).to receive(:perform_async)
         build.success!
       end
 
diff --git a/spec/models/deployment_spec.rb b/spec/models/deployment_spec.rb
index 1c7b11257ce..80bd47ec102 100644
--- a/spec/models/deployment_spec.rb
+++ b/spec/models/deployment_spec.rb
@@ -98,16 +98,36 @@ RSpec.describe Deployment do
     context 'when deployment runs' do
       let(:deployment) { create(:deployment) }
 
-      before do
-        deployment.run!
-      end
-
       it 'starts running' do
         freeze_time do
+          deployment.run!
+
           expect(deployment).to be_running
           expect(deployment.finished_at).to be_nil
         end
       end
+
+      it 'executes Deployments::ExecuteHooksWorker asynchronously' do
+        expect(Deployments::ExecuteHooksWorker)
+            .to receive(:perform_async).with(deployment.id)
+
+        deployment.run!
+      end
+
+      it 'does not execute Deployments::ExecuteHooksWorker when feature is disabled' do
+        stub_feature_flags(ci_send_deployment_hook_when_start: false)
+        expect(Deployments::ExecuteHooksWorker)
+            .not_to receive(:perform_async).with(deployment.id)
+
+        deployment.run!
+      end
+
+      it 'executes Deployments::ForwardDeploymentWorker asynchronously' do
+        expect(Deployments::ForwardDeploymentWorker)
+            .to receive(:perform_async).once.with(deployment.id)
+
+        deployment.run!
+      end
     end
 
     context 'when deployment succeeded' do
@@ -122,15 +142,15 @@ RSpec.describe Deployment do
         end
       end
 
-      it 'executes Deployments::SuccessWorker asynchronously' do
-        expect(Deployments::SuccessWorker)
+      it 'executes Deployments::UpdateEnvironmentWorker asynchronously' do
+        expect(Deployments::UpdateEnvironmentWorker)
           .to receive(:perform_async).with(deployment.id)
 
         deployment.succeed!
       end
 
-      it 'executes Deployments::FinishedWorker asynchronously' do
-        expect(Deployments::FinishedWorker)
+      it 'executes Deployments::ExecuteHooksWorker asynchronously' do
+        expect(Deployments::ExecuteHooksWorker)
           .to receive(:perform_async).with(deployment.id)
 
         deployment.succeed!
@@ -149,12 +169,19 @@ RSpec.describe Deployment do
         end
       end
 
-      it 'executes Deployments::FinishedWorker asynchronously' do
-        expect(Deployments::FinishedWorker)
+      it 'executes Deployments::LinkMergeRequestWorker asynchronously' do
+        expect(Deployments::LinkMergeRequestWorker)
           .to receive(:perform_async).with(deployment.id)
 
         deployment.drop!
       end
+
+      it 'executes Deployments::ExecuteHooksWorker asynchronously' do
+        expect(Deployments::ExecuteHooksWorker)
+            .to receive(:perform_async).with(deployment.id)
+
+        deployment.drop!
+      end
     end
 
     context 'when deployment was canceled' do
@@ -169,12 +196,19 @@ RSpec.describe Deployment do
         end
       end
 
-      it 'executes Deployments::FinishedWorker asynchronously' do
-        expect(Deployments::FinishedWorker)
+      it 'executes Deployments::LinkMergeRequestWorker asynchronously' do
+        expect(Deployments::LinkMergeRequestWorker)
           .to receive(:perform_async).with(deployment.id)
 
         deployment.cancel!
       end
+
+      it 'executes Deployments::ExecuteHooksWorker asynchronously' do
+        expect(Deployments::ExecuteHooksWorker)
+            .to receive(:perform_async).with(deployment.id)
+
+        deployment.cancel!
+      end
     end
   end
 
@@ -580,9 +614,10 @@ RSpec.describe Deployment do
       expect(deploy).to be_success
     end
 
-    it 'schedules SuccessWorker and FinishedWorker when finishing a deploy' do
-      expect(Deployments::SuccessWorker).to receive(:perform_async)
-      expect(Deployments::FinishedWorker).to receive(:perform_async)
+    it 'schedules workers when finishing a deploy' do
+      expect(Deployments::UpdateEnvironmentWorker).to receive(:perform_async)
+      expect(Deployments::LinkMergeRequestWorker).to receive(:perform_async)
+      expect(Deployments::ExecuteHooksWorker).to receive(:perform_async)
 
       deploy.update_status('success')
     end
diff --git a/spec/models/project_services/chat_message/deployment_message_spec.rb b/spec/models/project_services/chat_message/deployment_message_spec.rb
index 9c361f90ae0..6bdf2120b36 100644
--- a/spec/models/project_services/chat_message/deployment_message_spec.rb
+++ b/spec/models/project_services/chat_message/deployment_message_spec.rb
@@ -70,6 +70,17 @@ RSpec.describe ChatMessage::DeploymentMessage do
 
       expect(message.pretext).to eq('Deploy to staging unknown')
     end
+
+    it 'returns a message for a running deployment' do
+      data = {
+          status: 'running',
+          environment: 'production'
+      }
+
+      message = described_class.new(data)
+
+      expect(message.pretext).to eq('Starting deploy to production')
+    end
   end
 
   describe '#attachments' do
diff --git a/spec/services/deployments/create_service_spec.rb b/spec/services/deployments/create_service_spec.rb
index d1f977c28d3..2d157c9d114 100644
--- a/spec/services/deployments/create_service_spec.rb
+++ b/spec/services/deployments/create_service_spec.rb
@@ -19,8 +19,9 @@ RSpec.describe Deployments::CreateService do
         status: 'success'
       )
 
-      expect(Deployments::SuccessWorker).to receive(:perform_async)
-      expect(Deployments::FinishedWorker).to receive(:perform_async)
+      expect(Deployments::UpdateEnvironmentWorker).to receive(:perform_async)
+      expect(Deployments::LinkMergeRequestWorker).to receive(:perform_async)
+      expect(Deployments::ExecuteHooksWorker).to receive(:perform_async)
 
       expect(service.execute).to be_persisted
     end
@@ -34,8 +35,9 @@ RSpec.describe Deployments::CreateService do
         tag: false
       )
 
-      expect(Deployments::SuccessWorker).not_to receive(:perform_async)
-      expect(Deployments::FinishedWorker).not_to receive(:perform_async)
+      expect(Deployments::UpdateEnvironmentWorker).not_to receive(:perform_async)
+      expect(Deployments::LinkMergeRequestWorker).not_to receive(:perform_async)
+      expect(Deployments::ExecuteHooksWorker).not_to receive(:perform_async)
 
       expect(service.execute).to be_persisted
     end
diff --git a/spec/services/deployments/after_create_service_spec.rb b/spec/services/deployments/update_environment_service_spec.rb
similarity index 95%
rename from spec/services/deployments/after_create_service_spec.rb
rename to spec/services/deployments/update_environment_service_spec.rb
index ee9b008c2f8..66564a1042f 100644
--- a/spec/services/deployments/after_create_service_spec.rb
+++ b/spec/services/deployments/update_environment_service_spec.rb
@@ -2,7 +2,7 @@
 
 require 'spec_helper'
 
-RSpec.describe Deployments::AfterCreateService do
+RSpec.describe Deployments::UpdateEnvironmentService do
   let(:user) { create(:user) }
   let(:project) { create(:project, :repository) }
   let(:options) { { name: 'production' } }
@@ -31,7 +31,8 @@ RSpec.describe Deployments::AfterCreateService do
   subject(:service) { described_class.new(deployment) }
 
   before do
-    allow(Deployments::FinishedWorker).to receive(:perform_async)
+    allow(Deployments::LinkMergeRequestWorker).to receive(:perform_async)
+    allow(Deployments::ExecuteHooksWorker).to receive(:perform_async)
     job.success! # Create/Succeed deployment
   end
 
@@ -100,8 +101,8 @@ RSpec.describe Deployments::AfterCreateService do
       end
 
       before do
-        environment.update(name: 'review-apps/master')
-        job.update(environment: 'review-apps/$CI_COMMIT_REF_NAME')
+        environment.update!(name: 'review-apps/master')
+        job.update!(environment: 'review-apps/$CI_COMMIT_REF_NAME')
       end
 
       it 'does not create a new environment' do
@@ -241,7 +242,7 @@ RSpec.describe Deployments::AfterCreateService do
         end
 
         it 'does not raise errors if the merge request does not have a metrics record' do
-          merge_request.metrics.destroy
+          merge_request.metrics.destroy!
 
           expect(merge_request.reload.metrics).to be_nil
           expect { service.execute }.not_to raise_error
diff --git a/spec/workers/deployments/execute_hooks_worker_spec.rb b/spec/workers/deployments/execute_hooks_worker_spec.rb
new file mode 100644
index 00000000000..fb1dc8cf290
--- /dev/null
+++ b/spec/workers/deployments/execute_hooks_worker_spec.rb
@@ -0,0 +1,51 @@
+# frozen_string_literal: true
+
+require 'spec_helper'
+
+RSpec.describe Deployments::ExecuteHooksWorker do
+  let(:worker) { described_class.new }
+
+  describe '#perform' do
+    before do
+      allow(ProjectServiceWorker).to receive(:perform_async)
+    end
+
+    it 'executes project services for deployment_hooks' do
+      deployment = create(:deployment, :running)
+      project = deployment.project
+      service = create(:service, type: 'SlackService', project: project, deployment_events: true, active: true)
+
+      expect(ProjectServiceWorker).to receive(:perform_async).with(service.id, an_instance_of(Hash))
+
+      worker.perform(deployment.id)
+    end
+
+    it 'does not execute an inactive service' do
+      deployment = create(:deployment, :running)
+      project = deployment.project
+      create(:service, type: 'SlackService', project: project, deployment_events: true, active: false)
+
+      expect(ProjectServiceWorker).not_to receive(:perform_async)
+
+      worker.perform(deployment.id)
+    end
+
+    it 'does not execute if a deployment does not exist' do
+      expect(ProjectServiceWorker).not_to receive(:perform_async)
+
+      worker.perform(non_existing_record_id)
+    end
+
+    it 'execute webhooks' do
+      deployment = create(:deployment, :running)
+      project = deployment.project
+      web_hook = create(:project_hook, deployment_events: true, project: project)
+
+      expect_next_instance_of(WebHookService, web_hook, an_instance_of(Hash), "deployment_hooks") do |service|
+        expect(service).to receive(:async_execute)
+      end
+
+      worker.perform(deployment.id)
+    end
+  end
+end
diff --git a/spec/workers/deployments/link_merge_request_worker_spec.rb b/spec/workers/deployments/link_merge_request_worker_spec.rb
new file mode 100644
index 00000000000..a55dd897bc7
--- /dev/null
+++ b/spec/workers/deployments/link_merge_request_worker_spec.rb
@@ -0,0 +1,71 @@
+# frozen_string_literal: true
+
+require 'spec_helper'
+
+RSpec.describe Deployments::LinkMergeRequestWorker do
+  subject(:worker) { described_class.new }
+
+  describe '#perform' do
+    it 'links merge requests to the deployment' do
+      deployment = create(:deployment)
+      service = instance_double(Deployments::LinkMergeRequestsService)
+
+      expect(Deployments::LinkMergeRequestsService)
+          .to receive(:new)
+                  .with(deployment)
+                  .and_return(service)
+
+      expect(service).to receive(:execute)
+
+      worker.perform(deployment.id)
+    end
+
+    it 'does not link merge requests when the deployment is not found' do
+      expect(Deployments::LinkMergeRequestsService).not_to receive(:new)
+
+      worker.perform(non_existing_record_id)
+    end
+  end
+
+  context 'idempotent' do
+    include_examples 'an idempotent worker' do
+      let(:project) { create(:project, :repository) }
+      let(:environment) { create(:environment, project: project) }
+      let(:deployment) { create(:deployment, :success, project: project, environment: environment) }
+      let(:job_args) { deployment.id }
+
+      it 'links merge requests to deployment' do
+        mr1 = create(
+          :merge_request,
+          :merged,
+          source_project: project,
+          target_project: project,
+          source_branch: 'source1',
+          target_branch: deployment.ref
+        )
+
+        mr2 = create(
+          :merge_request,
+          :merged,
+          source_project: project,
+          target_project: project,
+          source_branch: 'source2',
+          target_branch: deployment.ref
+        )
+
+        mr3 = create(
+          :merge_request,
+          :merged,
+          source_project: project,
+          target_project: project,
+          target_branch: 'foo'
+        )
+
+        subject
+
+        expect(deployment.merge_requests).to include(mr1, mr2)
+        expect(deployment.merge_requests).not_to include(mr3)
+      end
+    end
+  end
+end
diff --git a/spec/workers/deployments/success_worker_spec.rb b/spec/workers/deployments/success_worker_spec.rb
index 7c21a3147a7..d9996e66919 100644
--- a/spec/workers/deployments/success_worker_spec.rb
+++ b/spec/workers/deployments/success_worker_spec.rb
@@ -8,8 +8,8 @@ RSpec.describe Deployments::SuccessWorker do
   context 'when successful deployment' do
     let(:deployment) { create(:deployment, :success) }
 
-    it 'executes Deployments::AfterCreateService' do
-      expect(Deployments::AfterCreateService)
+    it 'executes Deployments::UpdateEnvironmentService' do
+      expect(Deployments::UpdateEnvironmentService)
         .to receive(:new).with(deployment).and_call_original
 
       subject
@@ -19,8 +19,8 @@ RSpec.describe Deployments::SuccessWorker do
   context 'when canceled deployment' do
     let(:deployment) { create(:deployment, :canceled) }
 
-    it 'does not execute Deployments::AfterCreateService' do
-      expect(Deployments::AfterCreateService).not_to receive(:new)
+    it 'does not execute Deployments::UpdateEnvironmentService' do
+      expect(Deployments::UpdateEnvironmentService).not_to receive(:new)
 
       subject
     end
@@ -29,8 +29,8 @@ RSpec.describe Deployments::SuccessWorker do
   context 'when deploy record does not exist' do
     let(:deployment) { nil }
 
-    it 'does not execute Deployments::AfterCreateService' do
-      expect(Deployments::AfterCreateService).not_to receive(:new)
+    it 'does not execute Deployments::UpdateEnvironmentService' do
+      expect(Deployments::UpdateEnvironmentService).not_to receive(:new)
 
       subject
     end
diff --git a/spec/workers/deployments/update_environment_worker_spec.rb b/spec/workers/deployments/update_environment_worker_spec.rb
new file mode 100644
index 00000000000..d67cbd62616
--- /dev/null
+++ b/spec/workers/deployments/update_environment_worker_spec.rb
@@ -0,0 +1,63 @@
+# frozen_string_literal: true
+
+require 'spec_helper'
+
+RSpec.describe Deployments::UpdateEnvironmentWorker do
+  subject(:worker) { described_class.new }
+
+  context 'when successful deployment' do
+    let(:deployment) { create(:deployment, :success) }
+
+    it 'executes Deployments::UpdateEnvironmentService' do
+      service = instance_double(Deployments::UpdateEnvironmentService)
+
+      expect(Deployments::UpdateEnvironmentService)
+          .to receive(:new)
+                  .with(deployment)
+                  .and_return(service)
+
+      expect(service).to receive(:execute)
+
+      worker.perform(deployment.id)
+    end
+  end
+
+  context 'when canceled deployment' do
+    let(:deployment) { create(:deployment, :canceled) }
+
+    it 'does not execute Deployments::UpdateEnvironmentService' do
+      expect(Deployments::UpdateEnvironmentService).not_to receive(:new)
+
+      worker.perform(deployment.id)
+    end
+  end
+
+  context 'when deploy record does not exist' do
+    it 'does not execute Deployments::UpdateEnvironmentService' do
+      expect(Deployments::UpdateEnvironmentService).not_to receive(:new)
+
+      worker.perform(non_existing_record_id)
+    end
+  end
+
+  context 'idempotent' do
+    include_examples 'an idempotent worker' do
+      let(:project) { create(:project, :repository) }
+      let(:environment) { create(:environment, name: 'production') }
+      let(:deployment) { create(:deployment, :success, project: project, environment: environment) }
+      let(:merge_request) { create(:merge_request, target_branch: 'master', source_branch: 'feature', source_project: project) }
+      let(:job_args) { deployment.id }
+
+      before do
+        merge_request.metrics.update!(merged_at: 1.hour.ago)
+      end
+
+      it 'updates merge requests metrics' do
+        subject
+
+        expect(merge_request.reload.metrics.first_deployed_to_production_at)
+            .to be_like_time(deployment.finished_at)
+      end
+    end
+  end
+end