diff --git a/app/jobs/delay_expired_issue_and_milestone_job.rb b/app/jobs/delay_expired_issue_and_milestone_job.rb
new file mode 100644
index 000000000..4bba7aaf1
--- /dev/null
+++ b/app/jobs/delay_expired_issue_and_milestone_job.rb
@@ -0,0 +1,16 @@
+class DelayExpiredIssueAndMilestoneJob < ApplicationJob
+  queue_as :message
+
+  def perform
+    Issue.where(due_date: Date.today + 1.days).find_each do |issue|
+      SendTemplateMessageJob.perform_later('IssueExpire', issue.id) if Site.has_notice_menu?
+    end
+    Version.where(effective_date: Date.today + 1.days).find_each do |version| 
+      SendTemplateMessageJob.perform_later('ProjectMilestoneEarlyExpired', version.id) if Site.has_notice_menu?
+    end
+    Version.where(effective_date: Date.today - 1.days).find_each do |version|
+      SendTemplateMessageJob.perform_later('ProjectMilestoneExpired', version.id) if Site.has_notice_menu?
+    end
+  end
+
+end
\ No newline at end of file
diff --git a/app/jobs/delay_expired_issue_job.rb b/app/jobs/delay_expired_issue_job.rb
deleted file mode 100644
index ed390e15b..000000000
--- a/app/jobs/delay_expired_issue_job.rb
+++ /dev/null
@@ -1,10 +0,0 @@
-class DelayExpiredIssueJob < ApplicationJob
-  queue_as :message
-
-  def perform
-    Issue.where(due_date: Date.today + 1.days).find_each do |issue|
-      SendTemplateMessageJob.perform_later('IssueExpire', issue.id) if Site.has_notice_menu?
-    end
-  end
-
-end
\ No newline at end of file
diff --git a/app/jobs/send_template_message_job.rb b/app/jobs/send_template_message_job.rb
index 05572d451..82f41cad2 100644
--- a/app/jobs/send_template_message_job.rb
+++ b/app/jobs/send_template_message_job.rb
@@ -221,6 +221,20 @@ class SendTemplateMessageJob < ApplicationJob
         receivers_email_string, email_title, email_content = MessageTemplate::ProjectMilestone.get_email_message_content(receiver, operator, milestone)
         Notice::Write::EmailCreateService.call(receivers_email_string, email_title, email_content)
       end
+    when 'ProjectMilestoneExpired'
+      milestone_id = args[0]
+      milestone = Version.find_by_id(milestone_id)
+      return unless milestone.present? && milestone&.project.present?
+      receivers = User.where(id: milestone.user_id)
+      receivers_string, content, notification_url = MessageTemplate::ProjectMilestoneExpired.get_message_content(receivers, milestone)
+      Notice::Write::CreateService.call(receivers_string, content, notification_url, source, {milestone_id: milestone_id, operator_id: operator_id})
+    when 'ProjectMilestoneEarlyExpired'
+      milestone_id = args[0]
+      milestone = Version.find_by_id(milestone_id)
+      return unless milestone.present? && milestone&.project.present?
+      receivers = User.where(id: milestone.user_id)
+      receivers_string, content, notification_url = MessageTemplate::ProjectMilestoneEarlyExpired.get_message_content(receivers, milestone)
+      Notice::Write::CreateService.call(receivers_string, content, notification_url, source, {milestone_id: milestone_id, operator_id: operator_id})
     when 'ProjectPraised'
       operator_id, project_id = args[0], args[1]
       operator = User.find_by_id(operator_id)
diff --git a/app/models/message_template.rb b/app/models/message_template.rb
index 7ab7fdad8..75d64fa95 100644
--- a/app/models/message_template.rb
+++ b/app/models/message_template.rb
@@ -52,6 +52,8 @@ class MessageTemplate < ApplicationRecord
     self.create(type: 'MessageTemplate::ProjectMilestone', sys_notice: '{nickname1}在 <b>{nickname2}/{repository}</b> 创建了一个里程碑：<b>{name}</b>', notification_url: '{baseurl}/{owner}/{identifier}/milestones/{id}', email: email_html, email_title: "#{PLATFORM}: {nickname1} 在 {nickname2}/{repository} 新建了一个里程碑")
     email_html = File.read("#{email_template_html_dir}/project_milestone_completed.html")
     self.create(type: 'MessageTemplate::ProjectMilestoneCompleted', sys_notice: '在 <b>{nickname}/{repository}</b> 仓库，里程碑 <b>{name}</b> 的完成度已达到100%', notification_url: '{baseurl}/{owner}/{identifier}/milestones/{id}', email: email_html, email_title: "#{PLATFORM}: 仓库 {nickname}/{repository} 有里程碑已完成")
+    self.create(type: 'MessageTemplate::ProjectMilestoneEarlyExpired', sys_notice: '您创建的里程碑 <b>{name}</b> 已临近截止日期，请尽快处理.', notification_url: '{baseurl}/{owner}/{identifier}/milestones/{id}')
+    self.create(type: 'MessageTemplate::ProjectMilestoneExpired', sys_notice: '您创建的里程碑 <b>{name}</b> 已逾期，请及时更新进度或联系项目团队.', notification_url: '{baseurl}/{owner}/{identifier}/milestones/{id}')
     self.create(type: 'MessageTemplate::ProjectPraised', sys_notice: '<b>{nickname1}</b> 点赞了你管理的仓库 <b>{nickname2}/{repository}</b>', notification_url: '{baseurl}/{login}')
     self.create(type: 'MessageTemplate::ProjectOpenDevOps', sys_notice: '您的仓库 <b>{repository}</b> 已成功开通引擎服务，可通过简单的节点编排完成自动化集成与部署。欢迎体验！', notification_url: '{baseurl}/{owner}/{identifier}/devops')
     email_html = File.read("#{email_template_html_dir}/project_pull_request.html")
diff --git a/app/models/message_template/project_milestone_early_expired.rb b/app/models/message_template/project_milestone_early_expired.rb
new file mode 100644
index 000000000..5539fc362
--- /dev/null
+++ b/app/models/message_template/project_milestone_early_expired.rb
@@ -0,0 +1,70 @@
+# == Schema Information
+#
+# Table name: message_templates
+#
+#  id               :integer          not null, primary key
+#  type             :string(255)
+#  sys_notice       :text(65535)
+#  email            :text(65535)
+#  created_at       :datetime         not null
+#  updated_at       :datetime         not null
+#  notification_url :string(255)
+#  email_title      :string(255)
+#
+
+# 我管理的仓库有里程碑完成
+class MessageTemplate::ProjectMilestoneEarlyExpired < MessageTemplate
+
+  # MessageTemplate::ProjectMilestoneEarlyExpired.get_message_content(User.where(login: 'yystopf'), Version.find(7))
+  def self.get_message_content(receivers, milestone)
+    receivers.each do |receiver|
+      if receiver.user_template_message_setting.present? 
+        send_setting = receiver.user_template_message_setting.notification_body["ManageProject::MilestoneEarlyExpired"]
+        send_setting = send_setting.nil? ? UserTemplateMessageSetting.init_notification_body["ManageProject::MilestoneEarlyExpired"] : send_setting
+        receivers = receivers.where.not(id: receiver.id) unless send_setting
+      end
+    end
+    return '', '', '' if receivers.blank?
+    project = milestone&.project 
+    owner = project&.owner 
+    content = sys_notice.gsub('{nickname}', owner&.real_name).gsub('{repository}', project&.name).gsub('{name}', milestone&.name)
+    url = notification_url.gsub('{owner}', owner&.login).gsub('{identifier}', project&.identifier).gsub('{id}', milestone&.id.to_s)
+    
+    return receivers_string(receivers), content, url
+  rescue => e
+    Rails.logger.info("MessageTemplate::MilestoneEarlyExpired.get_message_content [ERROR] #{e}")
+    return '', '', ''
+  end
+
+  def self.get_email_message_content(receiver, milestone)
+    if receiver.user_template_message_setting.present? 
+      send_setting = receiver.user_template_message_setting.email_body["ManageProject::MilestoneEarlyExpired"]
+      send_setting = send_setting.nil? ? UserTemplateMessageSetting.init_email_body["ManageProject::MilestoneEarlyExpired"] : send_setting
+      return '', '', '' unless send_setting
+      project = milestone&.project 
+      owner = project&.owner 
+      title = email_title
+      title.gsub!('{nickname}', owner&.real_name)
+      title.gsub!('{repository}', project&.name)
+  
+      content = email 
+      content.gsub!('{receiver}', receiver&.real_name)
+      content.gsub!('{baseurl}', base_url)
+      content.gsub!('{nickname}', owner&.real_name)
+      content.gsub!('{repository}', project&.name)
+      content.gsub!('{login}', owner&.login)
+      content.gsub!('{identifier}', project&.identifier)
+      content.gsub!('{id}', milestone&.id.to_s)
+      content.gsub!('{name}', milestone&.name)
+      content.gsub!('{platform}', PLATFORM)
+      
+      return receiver&.mail, title, content
+    else
+      return '', '', ''
+    end
+   
+  rescue => e
+    Rails.logger.info("MessageTemplate::MilestoneEarlyExpired.get_email_message_content [ERROR] #{e}")
+    return '', '', ''
+  end
+end
diff --git a/app/models/message_template/project_milestone_expired.rb b/app/models/message_template/project_milestone_expired.rb
new file mode 100644
index 000000000..de6b8c10c
--- /dev/null
+++ b/app/models/message_template/project_milestone_expired.rb
@@ -0,0 +1,70 @@
+# == Schema Information
+#
+# Table name: message_templates
+#
+#  id               :integer          not null, primary key
+#  type             :string(255)
+#  sys_notice       :text(65535)
+#  email            :text(65535)
+#  created_at       :datetime         not null
+#  updated_at       :datetime         not null
+#  notification_url :string(255)
+#  email_title      :string(255)
+#
+
+# 我管理的仓库有里程碑完成
+class MessageTemplate::ProjectMilestoneExpired < MessageTemplate
+
+  # MessageTemplate::ProjectMilestoneExpired.get_message_content(User.where(login: 'yystopf'), Version.find(7))
+  def self.get_message_content(receivers, milestone)
+    receivers.each do |receiver|
+      if receiver.user_template_message_setting.present? 
+        send_setting = receiver.user_template_message_setting.notification_body["ManageProject::MilestoneExpired"]
+        send_setting = send_setting.nil? ? UserTemplateMessageSetting.init_notification_body["ManageProject::MilestoneExpired"] : send_setting
+        receivers = receivers.where.not(id: receiver.id) unless send_setting
+      end
+    end
+    return '', '', '' if receivers.blank?
+    project = milestone&.project 
+    owner = project&.owner 
+    content = sys_notice.gsub('{nickname}', owner&.real_name).gsub('{repository}', project&.name).gsub('{name}', milestone&.name)
+    url = notification_url.gsub('{owner}', owner&.login).gsub('{identifier}', project&.identifier).gsub('{id}', milestone&.id.to_s)
+    
+    return receivers_string(receivers), content, url
+  rescue => e
+    Rails.logger.info("MessageTemplate::ProjectMilestoneExpired.get_message_content [ERROR] #{e}")
+    return '', '', ''
+  end
+
+  def self.get_email_message_content(receiver, milestone)
+    if receiver.user_template_message_setting.present? 
+      send_setting = receiver.user_template_message_setting.email_body["ManageProject::MilestoneExpired"]
+      send_setting = send_setting.nil? ? UserTemplateMessageSetting.init_email_body["ManageProject::MilestoneExpired"] : send_setting
+      return '', '', '' unless send_setting
+      project = milestone&.project 
+      owner = project&.owner 
+      title = email_title
+      title.gsub!('{nickname}', owner&.real_name)
+      title.gsub!('{repository}', project&.name)
+  
+      content = email 
+      content.gsub!('{receiver}', receiver&.real_name)
+      content.gsub!('{baseurl}', base_url)
+      content.gsub!('{nickname}', owner&.real_name)
+      content.gsub!('{repository}', project&.name)
+      content.gsub!('{login}', owner&.login)
+      content.gsub!('{identifier}', project&.identifier)
+      content.gsub!('{id}', milestone&.id.to_s)
+      content.gsub!('{name}', milestone&.name)
+      content.gsub!('{platform}', PLATFORM)
+      
+      return receiver&.mail, title, content
+    else
+      return '', '', ''
+    end
+   
+  rescue => e
+    Rails.logger.info("MessageTemplate::ProjectMilestoneExpired.get_email_message_content [ERROR] #{e}")
+    return '', '', ''
+  end
+end
diff --git a/app/models/user_template_message_setting.rb b/app/models/user_template_message_setting.rb
index 49db51d4d..7e855b768 100644
--- a/app/models/user_template_message_setting.rb
+++ b/app/models/user_template_message_setting.rb
@@ -44,6 +44,8 @@ class UserTemplateMessageSetting < ApplicationRecord
       "ManageProject::Forked": true,
       "ManageProject::Milestone": true,
       "ManageProject::MilestoneCompleted": true,
+      "ManageProject::MilestoneExpired": true,
+      "ManageProject::MilestoneEarlyExpired": true,
     }.stringify_keys!
   end
 
@@ -65,6 +67,8 @@ class UserTemplateMessageSetting < ApplicationRecord
       "ManageProject::Forked": false,
       "ManageProject::Milestone": false,
       "ManageProject::MilestoneCompleted": false,
+      "ManageProject::MilestoneExpired": false,
+      "ManageProject::MilestoneEarlyExpired": false,
     }.stringify_keys!
   end
 
diff --git a/app/models/version.rb b/app/models/version.rb
index 82474f55e..5787116db 100644
--- a/app/models/version.rb
+++ b/app/models/version.rb
@@ -68,5 +68,7 @@ class Version < ApplicationRecord
 
   def send_update_message_to_notice_system
     SendTemplateMessageJob.perform_later('ProjectMilestoneCompleted', self.id) if Site.has_notice_menu? && self.issue_percent == 1.0
+    SendTemplateMessageJob.perform_later('ProjectMilestoneEarlyExpired', self.id) if Site.has_notice_menu? && self.effective_date == Date.today + 1.days 
+    SendTemplateMessageJob.perform_later('ProjectMilestoneExpired', self.id) if Site.has_notice_menu? && self.effective_date == Date.today - 1.days 
   end
 end
diff --git a/config/sidekiq_cron.yml b/config/sidekiq_cron.yml
index 448e9c945..c31ce2575 100644
--- a/config/sidekiq_cron.yml
+++ b/config/sidekiq_cron.yml
@@ -5,5 +5,5 @@ sync_gitea_repo_update_time:
 
 delay_expired_issue:
   cron: "0 0 * * *"
-  class: "DelayExpiredIssueJob"
+  class: "DelayExpiredIssueAndMilestoneJob"
   queue: message