diff --git a/app/models/issue.rb b/app/models/issue.rb
index 8ba261bb1f..a8810611cb 100644
--- a/app/models/issue.rb
+++ b/app/models/issue.rb
@@ -1930,6 +1930,13 @@ class Issue < ActiveRecord::Base
   # Closes duplicates if the issue is being closed
   def close_duplicates
     if Setting.close_duplicate_issues? && closing?
+      # Check that there are no circular dependency of relationships
+      duplicate_issue_ids = circular_dependency_duplicate_issue_ids(duplicates)
+      if duplicate_issue_ids.include?(self.id)
+        self.errors.add :base, :circular_dependency
+        throw :abort
+      end
+
       duplicates.each do |duplicate|
         # Reload is needed in case the duplicate was updated by a previous duplicate
         duplicate.reload
@@ -1946,6 +1953,17 @@ class Issue < ActiveRecord::Base
     end
   end
 
+  def circular_dependency_duplicate_issue_ids(issues, duplicate_ids = [])
+    issues.each do |issue|
+      next if duplicate_ids.include?(issue.id)
+
+      duplicate_ids << issue.id
+      duplicate_ids.concat(circular_dependency_duplicate_issue_ids(issue.duplicates, duplicate_ids))
+      duplicate_ids.uniq!
+    end
+    duplicate_ids
+  end
+
   # Make sure updated_on is updated when adding a note and set updated_on now
   # so we can set closed_on with the same value on closing
   def force_updated_on_change
diff --git a/app/models/issue_relation.rb b/app/models/issue_relation.rb
index 808686a162..a3dcffdf3b 100644
--- a/app/models/issue_relation.rb
+++ b/app/models/issue_relation.rb
@@ -238,6 +238,10 @@ class IssueRelation < ActiveRecord::Base
       issue_from.blocks? issue_to
     when 'blocks'
       issue_to.blocks? issue_from
+    when 'duplicated'
+      self.class.exists?(issue_from_id: issue_from, issue_to_id: issue_to, relation_type: TYPE_DUPLICATES)
+    when 'duplicates'
+      self.class.exists?(issue_from_id: issue_to, issue_to_id: issue_from, relation_type: TYPE_DUPLICATES)
     when 'relates'
       self.class.where(issue_from_id: issue_to, issue_to_id: issue_from).present?
     else
diff --git a/test/unit/issue_relation_test.rb b/test/unit/issue_relation_test.rb
index f2cf39dcc1..b857a17b8b 100644
--- a/test/unit/issue_relation_test.rb
+++ b/test/unit/issue_relation_test.rb
@@ -199,6 +199,27 @@ class IssueRelationTest < ActiveSupport::TestCase
     assert_not_equal [], r.errors[:base]
   end
 
+  def test_validates_circular_dependency_on_reverse_relations_using_duplicates
+    with_locale 'en' do
+      IssueRelation.delete_all
+      issue1 = issues(:issues_001)
+      issue2 = issues(:issues_002)
+      assert(
+        IssueRelation.create!(
+          :issue_from => issue1, :issue_to => issue2,
+          :relation_type => IssueRelation::TYPE_DUPLICATES
+        )
+      )
+      r =
+        IssueRelation.new(
+          :issue_from => issue2, :issue_to => issue1,
+          :relation_type => IssueRelation::TYPE_DUPLICATES
+        )
+      assert !r.save
+      assert_include 'This relation would create a circular dependency', r.errors.full_messages
+    end
+  end
+
   def test_create_with_initialized_journals_should_create_journals
     from = Issue.find(1)
     to   = Issue.find(2)
diff --git a/test/unit/issue_test.rb b/test/unit/issue_test.rb
index 95812376a4..d59959c595 100644
--- a/test/unit/issue_test.rb
+++ b/test/unit/issue_test.rb
@@ -1615,6 +1615,42 @@ class IssueTest < ActiveSupport::TestCase
     assert !issue1.reload.closed?
   end
 
+  def test_should_not_close_duplicated_issue_with_multiple_circular_dependencies
+    IssueRelation.delete_all
+    issue1 = Issue.generate!
+    issue2 = Issue.generate!
+    issue3 = Issue.generate!
+
+    IssueRelation.create(:issue_from => issue1, :issue_to => issue2,
+                         :relation_type => IssueRelation::TYPE_DUPLICATES).save!(:validate => false)
+    IssueRelation.create(:issue_from => issue2, :issue_to => issue3,
+                         :relation_type => IssueRelation::TYPE_DUPLICATES).save!(:validate => false)
+    IssueRelation.create(:issue_from => issue3, :issue_to => issue1,
+                         :relation_type => IssueRelation::TYPE_DUPLICATES).save!(:validate => false)
+
+    issue2_a = Issue.generate!
+    issue2_b = Issue.generate!
+
+    IssueRelation.create(:issue_from => issue2, :issue_to => issue2_a,
+                         :relation_type => IssueRelation::TYPE_DUPLICATES).save!(:validate => false)
+    IssueRelation.create(:issue_from => issue2_a, :issue_to => issue2_b,
+                         :relation_type => IssueRelation::TYPE_DUPLICATES).save!(:validate => false)
+    IssueRelation.create(:issue_from => issue2_b, :issue_to => issue2,
+                         :relation_type => IssueRelation::TYPE_DUPLICATES).save!(:validate => false)
+
+    assert_equal 1, issue1.duplicates.count
+    assert_equal [issue3], issue1.duplicates
+    assert_equal 1, issue3.duplicates.count
+    assert_equal [issue2], issue3.duplicates
+    assert_equal 2, issue2.duplicates.count
+    assert_equal [issue1, issue2_b], issue2.duplicates.sort
+
+    issue1.init_journal(users(:users_002), "Closing issue")
+    issue1.status = IssueStatus.where(:is_closed => true).first
+    assert !issue1.save
+    assert_include 'This relation would create a circular dependency', issue1.errors.full_messages
+  end
+
   def test_assignable_versions
     issue = Issue.new(:project_id => 1, :tracker_id => 1, :author_id => 1,
                       :status_id => 1, :fixed_version_id => 1,