diff --git a/app/models/concerns/issuable.rb b/app/models/concerns/issuable.rb
index db73588a948..4b21cf02919 100644
--- a/app/models/concerns/issuable.rb
+++ b/app/models/concerns/issuable.rb
@@ -37,8 +37,8 @@ module Issuable
     scope :closed, -> { with_state(:closed) }
 
     scope :left_joins_milestones,    -> { joins("LEFT OUTER JOIN milestones ON #{table_name}.milestone_id = milestones.id") }
-    scope :order_milestone_due_desc, -> { outer_join_milestone.reorder('milestones.due_date IS NULL ASC, milestones.due_date DESC, milestones.id DESC') }
-    scope :order_milestone_due_asc, -> { outer_join_milestone.reorder('milestones.due_date IS NULL ASC, milestones.due_date ASC, milestones.id ASC') }
+    scope :order_milestone_due_desc, -> { left_joins_milestones.reorder('CASE WHEN milestones.due_date IS NULL then 0 ELSE 1 END DESC, CASE WHEN milestones.id IS NULL then 0 ELSE 1 END DESC, milestones.due_date DESC') }
+    scope :order_milestone_due_asc,  -> { left_joins_milestones.reorder('CASE WHEN milestones.due_date IS NULL then 1 ELSE 0 END ASC, CASE WHEN milestones.id IS NULL then 1 ELSE 0 END ASC, milestones.due_date ASC') }
 
     scope :without_label, -> { joins("LEFT OUTER JOIN label_links ON label_links.target_type = '#{name}' AND label_links.target_id = #{table_name}.id").where(label_links: { id: nil }) }
     scope :join_project, -> { joins(:project) }
diff --git a/spec/features/issues/filter_by_milestone_spec.rb b/spec/features/issues/filter_by_milestone_spec.rb
index 99445185893..666993d19d4 100644
--- a/spec/features/issues/filter_by_milestone_spec.rb
+++ b/spec/features/issues/filter_by_milestone_spec.rb
@@ -15,14 +15,14 @@ feature 'Issue filtering by Milestone', feature: true do
   end
 
   context 'filters by upcoming milestone', js: true do
-    it 'should not show issues with no expiry' do
+    it 'should show issues with no expiry' do
       create(:issue, project: project)
       create(:issue, project: project, milestone: milestone)
 
       visit_issues(project)
       filter_by_milestone(Milestone::Upcoming.title)
 
-      expect(page).to have_css('.issue', count: 0)
+      expect(page).to have_css('.issue', count: 2)
     end
 
     it 'should show issues in future' do
@@ -36,7 +36,7 @@ feature 'Issue filtering by Milestone', feature: true do
       expect(page).to have_css('.issue', count: 1)
     end
 
-    it 'should not show issues in past' do
+    it 'should show issues in past' do
       milestone = create(:milestone, project: project, due_date: Date.yesterday)
       create(:issue, project: project)
       create(:issue, project: project, milestone: milestone)
@@ -44,7 +44,7 @@ feature 'Issue filtering by Milestone', feature: true do
       visit_issues(project)
       filter_by_milestone(Milestone::Upcoming.title)
 
-      expect(page).to have_css('.issue', count: 0)
+      expect(page).to have_css('.issue', count: 2)
     end
   end
 
diff --git a/spec/features/merge_requests/filter_by_milestone_spec.rb b/spec/features/merge_requests/filter_by_milestone_spec.rb
index e3ecd60a5f3..db3efca21c8 100644
--- a/spec/features/merge_requests/filter_by_milestone_spec.rb
+++ b/spec/features/merge_requests/filter_by_milestone_spec.rb
@@ -21,14 +21,14 @@ feature 'Merge Request filtering by Milestone', feature: true do
   end
 
   context 'filters by upcoming milestone', js: true do
-    it 'should not show issues with no expiry' do
+    it 'should show issues with no expiry' do
       create(:merge_request, :with_diffs, source_project: project)
       create(:merge_request, :simple, source_project: project, milestone: milestone)
 
       visit_merge_requests(project)
       filter_by_milestone(Milestone::Upcoming.title)
 
-      expect(page).to have_css('.merge-request', count: 0)
+      expect(page).to have_css('.merge-request', count: 2)
     end
 
     it 'should show issues in future' do
@@ -42,7 +42,7 @@ feature 'Merge Request filtering by Milestone', feature: true do
       expect(page).to have_css('.merge-request', count: 1)
     end
 
-    it 'should not show issues in past' do
+    it 'should show issues in past' do
       milestone = create(:milestone, project: project, due_date: Date.yesterday)
       create(:merge_request, :with_diffs, source_project: project)
       create(:merge_request, :simple, source_project: project, milestone: milestone)
@@ -50,7 +50,7 @@ feature 'Merge Request filtering by Milestone', feature: true do
       visit_merge_requests(project)
       filter_by_milestone(Milestone::Upcoming.title)
 
-      expect(page).to have_css('.merge-request', count: 0)
+      expect(page).to have_css('.merge-request', count: 2)
     end
   end
 
diff --git a/spec/models/concerns/issuable_spec.rb b/spec/models/concerns/issuable_spec.rb
index fa06a6f7ecf..2bb770df4fd 100644
--- a/spec/models/concerns/issuable_spec.rb
+++ b/spec/models/concerns/issuable_spec.rb
@@ -1,7 +1,7 @@
 require 'spec_helper'
 
 describe Issue, "Issuable" do
-  let!(:issue) { create(:issue) }
+  let(:issue) { create(:issue) }
   let(:user) { create(:user) }
 
   describe "Associations" do
@@ -119,6 +119,8 @@ describe Issue, "Issuable" do
     #Issues/MRs with milestones ordered by date
     #Issues/MRs with milestones without dates
     #Issues/MRs without milestones
+
+    let!(:issue) { create(:issue) }
     let(:project) { issue.project }
     let!(:early_milestone) { create(:milestone, project: project, due_date: 10.days.from_now) }
     let!(:late_milestone) { create(:milestone, project: project, due_date: 30.days.from_now) }