diff --git a/lib/gollum/frontend/public/gollum/javascript/editor/langs/markdown.js b/lib/gollum/frontend/public/gollum/javascript/editor/langs/markdown.js
index 923a5458..0e1c24f9 100644
--- a/lib/gollum/frontend/public/gollum/javascript/editor/langs/markdown.js
+++ b/lib/gollum/frontend/public/gollum/javascript/editor/langs/markdown.js
@@ -44,11 +44,22 @@ var MarkDown = {
                               search: /(.+)([\n]?)/g,
                               replace: "* $1$2"
                             },
-
-  /* This looks silly but is completely valid Markdown */
+  /* based on rdoc.js */
   'function-ol'   :         {
-                              search: /(.+)([\n]?)/g,
-                              replace: "1. $1$2"
+                                exec: function( txt, selText, $field ) {
+                                  var count = 1;
+                                  // split into lines
+                                  var repText = '';
+                                  var lines = selText.split("\n");
+                                  var hasContent = /[\w]+/;
+                                  for ( var i = 0; i < lines.length; i++ ) {
+                                    if ( hasContent.test(lines[i]) ) {
+                                      repText += (i + 1).toString() + '. ' +
+                                      lines[i] + "\n";
+                                    }
+                                  }
+                                  $.GollumEditor.replaceSelection( repText );
+                                }
                             },
 
   'function-blockquote' :   {