diff --git a/plugins/media/library.js b/plugins/media/library.js
index 1295ad5..2cc4aa6 100644
--- a/plugins/media/library.js
+++ b/plugins/media/library.js
@@ -51,16 +51,66 @@
       // This is pretty hacked for now.
       //
       var imgElement = $(this.stripDivs(formattedMedia));
-      this.addImageAttributes(imgElement, mediaFile.fid, viewMode, options);
+      elements = this.correctlyApplyAttributes(imgElement, mediaFile.fid, viewMode, options);
 
-      var toInsert = this.outerHTML(imgElement);
-      // Create an inline tag
-      var inlineTag = Drupal.settings.ckeditor.plugins['media'].createTag(imgElement);
+      var toInsert = this.outerHTML(elements['imgElement']);
+      // Create an inline tag making sure to use the part of the insertion (the
+      // <img>) that should actually get tokenized.
+      var inlineTag = this.createTag(elements['actualImgElement']);
       // Add it to the tag map in case the user switches input formats
       Drupal.settings.tagmap[inlineTag] = toInsert;
       ckeditorInstance.insertHtml(toInsert);
     },
 
+    correctlyApplyAttributes: function (imgElement, fid, view_mode, additional) {
+
+      if (imgElement.is('img')) {
+        // Store the actual <img> for use later in the createTag call that
+        // creates the media token from the element.
+        var actualImgElement = imgElement;
+        // Add the correct classes that will cause the element to be tokenized.
+        this.addImageAttributes(imgElement, fid, view_mode, additional);
+        // Document tokens need to rerender the associated filename link next
+        // to the filetype icon.
+        if (imgElement.hasClass('document')) {
+          var attributes = this.getAttributesFromClass(actualImgElement.attr('class'));
+          if (attributes.filename && attributes.href) {
+            // Construct the link.
+            link = $('<a></a>').attr('href', attributes.href.value).text(attributes.filename.value);
+            // Reconstruct imgElement with the link attached.
+            imgElement = $('<span class="file"></span>').prepend(actualImgElement).append(link);
+          }
+        }
+      }
+      else {
+        // This is for inserting documents who come as a <span> wrapped around
+        // the document icon <img> and the filename linked to the file. In this
+        // case we need to apply the correct classes to the child <img> because
+        // it needs to become the media token, but we need to retain the
+        // wrapper <span> and linked filename.
+        var actualImgElement = $('img', imgElement);
+        // Remove the <img> that does not have the correct classes to make it a
+        // media token.
+        imgElement.remove('img');
+        // If element contains a filename link, add attributes that will be
+        // used later to rerender the link when converting the token back into
+        // html.
+        var link = $('a', imgElement);
+        if (link) {
+          actualImgElement.attr('filename', link.text()).attr('href', link.attr('href'));
+          actualImgElement.addClass('document');
+        }
+        // Add the correct classes that will cause the element to be tokenized.
+        this.addImageAttributes(actualImgElement, fid, view_mode, additional);
+        // Add back the <img>, this time with the correct classes to make it a
+        // media token.
+        imgElement = imgElement.prepend(actualImgElement);
+      }
+
+      return {'imgElement': imgElement, 'actualImgElement': actualImgElement};
+
+    },
+
     /**
        * Gets the HTML content of an element
        *
@@ -92,7 +142,7 @@
     stripDivs: function (formattedMedia) {
       // Check to see if the image tag has divs to strip
       var stripped = null;
-      if ($(formattedMedia).is('img')) {
+      if ($(formattedMedia).is('img') || $(formattedMedia).is('span')) {
         stripped = this.outerHTML($(formattedMedia));
       } else {
         stripped = this.outerHTML($('img', $(formattedMedia)));
@@ -128,8 +178,8 @@
             mediaObj = JSON.parse(_tag);
 
             var imgElement = $(mediaMarkup);
-            this.addImageAttributes(imgElement, mediaObj.fid, mediaObj.view_mode);
-            var toInsert = this.outerHTML(imgElement);
+            elements = this.correctlyApplyAttributes(imgElement, mediaObj.fid, mediaObj.view_mode, false);
+            var toInsert = this.outerHTML(elements['imgElement']);
             content = content.replace(inlineTag, toInsert);
           }
           else {
@@ -147,7 +197,12 @@
       var content = $('<div>' + content + '</div>');
       $('img.media-image',content).each(function (elem) {
         var tag = Drupal.settings.ckeditor.plugins['media'].createTag($(this));
-        $(this).replaceWith(tag);
+        if ($(this).hasClass('document') && $(this).parent('span').length > 0) {
+          $(this).parent('span').replaceWith(tag);
+        }
+        else {
+          $(this).replaceWith(tag);
+        }
         var newContent = content.html();
         var tagContent = $('<div></div>').append($(this)).html();
         Drupal.settings.tagmap[tag] = tagContent;
@@ -277,6 +332,14 @@
       if (typeOf) {
         imgElement.addClass('attr__typeof__' + typeOf);
       }
+      var filename = imgElement.attr('filename');
+      if (filename) {
+        imgElement.addClass('attr__filename__' + filename);
+      }
+      var href = imgElement.attr('href');
+      if (href) {
+        imgElement.addClass('attr__href__' + href);
+      }
       if (fid) {
         imgElement.addClass('img__fid__' + fid);
       }