diff --git a/data/interfaces/default/settings.html b/data/interfaces/default/settings.html
index 7cd614e0..c5d8fe37 100644
--- a/data/interfaces/default/settings.html
+++ b/data/interfaces/default/settings.html
@@ -2498,9 +2498,9 @@ $(document).ready(function() {
     });
 
     $("#regroup_history").click(function () {
-        var msg = 'Are you sure you want to regroup play history in the database?';
+        var msg = 'Are you sure you want to regroup play history in the database?<br /><br /><strong>This make take a long time for large databases.<br />Regrouping will continue in the background.</strong>';
         var url = 'regroup_history';
-        confirmAjaxCall(url, msg, null, 'Regrouping play history...');
+        confirmAjaxCall(url, msg);
     });
 
     $("#delete_temp_sessions").click(function () {
diff --git a/plexpy/activity_processor.py b/plexpy/activity_processor.py
index b1558a56..0437d2d5 100644
--- a/plexpy/activity_processor.py
+++ b/plexpy/activity_processor.py
@@ -719,8 +719,14 @@ class ActivityProcessor(object):
             "JOIN session_history_metadata ON session_history.id = session_history_metadata.id"
         )
         results = self.db.select(query)
+        count = len(results)
+        progress = 0
+
+        for i, session in enumerate(results, start=1):
+            if int(i / count * 10) > progress:
+                progress = int(i / count * 10)
+                logger.info("Tautulli ActivityProcessor :: Regrouping session history: %d%%", progress * 10)
 
-        for session in results:
             try:
                 self.group_history(session['id'], session)
             except Exception as e:
@@ -729,3 +735,7 @@ class ActivityProcessor(object):
 
         logger.info("Tautulli ActivityProcessor :: Regrouping session history complete.")
         return True
+
+
+def regroup_history():
+    ActivityProcessor().regroup_history()
diff --git a/plexpy/webserve.py b/plexpy/webserve.py
index 7549aefa..b98c9e7c 100644
--- a/plexpy/webserve.py
+++ b/plexpy/webserve.py
@@ -443,12 +443,10 @@ class WebInterface(object):
     def regroup_history(self, **kwargs):
         """ Regroup play history in the database."""
 
-        result = activity_processor.ActivityProcessor().regroup_history()
+        threading.Thread(target=activity_processor.regroup_history).start()
 
-        if result:
-            return {'result': 'success', 'message': 'Regrouped play history.'}
-        else:
-            return {'result': 'error', 'message': 'Regrouping play history failed.'}
+        return {'result': 'success',
+                'message': 'Regrouping play history started. Check the logs to monitor any problems.'}
 
     @cherrypy.expose
     @cherrypy.tools.json_out()