Fetch a new GAIA picture every time chrome://settings/manageProfile comes up.

chrome/browser/resources/options/manage_profile_overlay.js

 // Copyright (c) 2012 The Chromium Authors. All rights reserved.
 // Use of this source code is governed by a BSD-style license that can be
 // found in the LICENSE file.
 
 cr.define('options', function() {
   var OptionsPage = options.OptionsPage;
   var ArrayDataModel = cr.ui.ArrayDataModel;
 
   /**
    * ManageProfileOverlay class
@@ skipping 483 matching lines @@
                     [this.profileInfo_.filePath, iconURL]);
       }
     },
 
     /**
      * Updates the contents of the "Manage Profile" section of the dialog,
      * and shows that section.
      * @private
      */
     prepareForManageDialog_: function() {
+      chrome.send('refreshGaiaPicture');
       var profileInfo = BrowserOptions.getCurrentProfile();
       ManageProfileOverlay.setProfileInfo(profileInfo, 'manage');
       $('manage-profile-overlay-create').hidden = true;
       $('manage-profile-overlay-manage').hidden = false;
       $('manage-profile-overlay-delete').hidden = true;
       $('manage-profile-overlay-disconnect-managed').hidden = true;
       $('manage-profile-name').disabled = profileInfo.isManaged;
       this.hideErrorBubble_('manage');
     },
 
@@ skipping 337 matching lines @@
       return instance[name + '_'].apply(instance, arguments);
     };
   });
 
   // Export
   return {
     ManageProfileOverlay: ManageProfileOverlay,
     CreateProfileOverlay: CreateProfileOverlay,
   };
 });