diff --git a/app/models/issue_query.rb b/app/models/issue_query.rb
index 7701cbfe2..155462c64 100644
--- a/app/models/issue_query.rb
+++ b/app/models/issue_query.rb
@@ -526,6 +526,9 @@ class IssueQuery < Query
       c = sql_contains("a.filename", value.first)
       e = (operator == "~" ? "EXISTS" : "NOT EXISTS")
       "#{e} (SELECT 1 FROM #{Attachment.table_name} a WHERE a.container_type = 'Issue' AND a.container_id = #{Issue.table_name}.id AND #{c})"
+    when "^", "$"
+      c = sql_contains("a.filename", value.first, (operator == "^" ? :starts_with : :ends_with) => true)
+      "EXISTS (SELECT 1 FROM #{Attachment.table_name} a WHERE a.container_type = 'Issue' AND a.container_id = #{Issue.table_name}.id AND #{c})"
     end
   end
 
diff --git a/test/unit/query_test.rb b/test/unit/query_test.rb
index 84bb1e939..9a8bb3c84 100644
--- a/test/unit/query_test.rb
+++ b/test/unit/query_test.rb
@@ -1353,6 +1353,20 @@ class QueryTest < ActiveSupport::TestCase
     assert_nil issues.detect {|issue| issue.attachments.any? {|attachment| attachment.filename.include?('error281')}}
   end
 
+  def test_filter_on_attachment_when_starts_with
+    query = IssueQuery.new(:name => '_')
+    query.filters = {"attachment" => {:operator => '^', :values =>  ['testfile']}}
+    issues = find_issues_with_query(query)
+    assert_equal [14], issues.collect(&:id).sort
+  end
+
+  def test_filter_on_attachment_when_ends_with
+    query = IssueQuery.new(:name => '_')
+    query.filters = {"attachment" => {:operator => '$', :values =>  ['zip']}}
+    issues = find_issues_with_query(query)
+    assert_equal [3, 4], issues.collect(&:id).sort
+  end
+
   def test_filter_on_subject_when_starts_with
     query = IssueQuery.new(:name => '_')
     query.filters = {'subject' => {:operator => '^', :values => ['issue']}}