diff --git a/app/helpers/application_helper.rb b/app/helpers/application_helper.rb
index e181eea54..f923b7b6c 100644
--- a/app/helpers/application_helper.rb
+++ b/app/helpers/application_helper.rb
@@ -774,7 +774,7 @@ module ApplicationHelper
             end
           when 'attachment'
             attachments = options[:attachments] || (obj && obj.respond_to?(:attachments) ? obj.attachments : nil)
-            if attachments && attachment = attachments.detect {|a| a.filename == name }
+            if attachments && attachment = Attachment.latest_attach(attachments, name)
               link = link_to_attachment(attachment, :only_path => only_path, :download => true, :class => 'attachment')
             end
           when 'project'
diff --git a/test/object_helpers.rb b/test/object_helpers.rb
index 254b6040e..4b5fbdbbe 100644
--- a/test/object_helpers.rb
+++ b/test/object_helpers.rb
@@ -129,4 +129,16 @@ module ObjectHelpers
     board.save!
     board
   end
+
+  def Attachment.generate!(attributes={})
+    @generated_filename ||= 'testfile0'
+    @generated_filename.succ!
+    attributes = attributes.dup
+    attachment = Attachment.new(attributes)
+    attachment.container ||= Issue.find(1)
+    attachment.author ||= User.find(2)
+    attachment.filename = @generated_filename if attachment.filename.blank?
+    attachment.save!
+    attachment
+  end
 end
diff --git a/test/unit/helpers/application_helper_test.rb b/test/unit/helpers/application_helper_test.rb
index 2654a1017..f23417d1a 100644
--- a/test/unit/helpers/application_helper_test.rb
+++ b/test/unit/helpers/application_helper_test.rb
@@ -555,6 +555,15 @@ RAW
     to_test.each { |text, result| assert_equal "<p>#{result}</p>", textilizable(text, :attachments => Issue.find(3).attachments), "#{text} failed" }
   end
 
+  def test_attachment_link_should_link_to_latest_attachment
+    set_tmp_attachments_directory
+    a1 = Attachment.generate!(:filename => "test.txt", :created_on => 1.hour.ago)
+    a2 = Attachment.generate!(:filename => "test.txt")
+
+    assert_equal %(<p><a href="/attachments/download/#{a2.id}/test.txt" class="attachment">test.txt</a></p>),
+      textilizable('attachment:test.txt', :attachments => [a1, a2])
+  end
+
   def test_wiki_links
     to_test = {
       '[[CookBook documentation]]' => '<a href="/projects/ecookbook/wiki/CookBook_documentation" class="wiki-page">CookBook documentation</a>',