diff --git a/app/models/mailer.rb b/app/models/mailer.rb
index 468e6c21a..800fdde88 100644
--- a/app/models/mailer.rb
+++ b/app/models/mailer.rb
@@ -584,6 +584,7 @@ class Mailer < ActionMailer::Base
     issues_by_assignee.each do |assignee, issues|
       if assignee.is_a?(User) && assignee.active? && issues.present?
         visible_issues = issues.select {|i| i.visible?(assignee)}
+        visible_issues.sort!{|a, b| (b.due_date <=> a.due_date).nonzero? || (a.id <=> b.id)}
         reminder(assignee, visible_issues, days).deliver_later if visible_issues.present?
       end
     end
diff --git a/test/unit/mailer_test.rb b/test/unit/mailer_test.rb
index c340a41ff..913bce513 100644
--- a/test/unit/mailer_test.rb
+++ b/test/unit/mailer_test.rb
@@ -621,6 +621,25 @@ class MailerTest < ActiveSupport::TestCase
     end
   end
 
+  def test_reminders_should_sort_issues_by_due_date
+    user = User.find(2)
+    Issue.generate!(:assigned_to => user, :due_date => 5.days.from_now, :subject => 'baz')
+    Issue.generate!(:assigned_to => user, :due_date => 5.days.from_now, :subject => 'qux')
+    Issue.generate!(:assigned_to => user, :due_date => 6.days.from_now, :subject => 'foo')
+    Issue.generate!(:assigned_to => user, :due_date => 6.days.from_now, :subject => 'bar')
+    ActionMailer::Base.deliveries.clear
+
+    Mailer.reminders(:days => 7, :users => [user.id])
+    assert_equal 1, ActionMailer::Base.deliveries.size
+    assert_select_email do
+      assert_select 'li', 4
+      assert_select 'li:nth-child(1)', /foo/
+      assert_select 'li:nth-child(2)', /bar/
+      assert_select 'li:nth-child(3)', /baz/
+      assert_select 'li:nth-child(4)', /qux/
+    end
+  end
+
   def test_security_notification
     set_language_if_valid User.find(1).language
     with_settings :emails_footer => "footer without link" do