diff --git a/data/interfaces/default/settings.html b/data/interfaces/default/settings.html
index fd234da2..7cd614e0 100644
--- a/data/interfaces/default/settings.html
+++ b/data/interfaces/default/settings.html
@@ -132,12 +132,6 @@
                             </label>
                             <p class="help-block">Change the "<em>Play by day of week</em>" graph to start on Monday. Default is start on Sunday.</p>
                         </div>
-                        <div class="checkbox advanced-setting">
-                            <label>
-                                <input type="checkbox" id="group_history_tables" name="group_history_tables" value="1" ${config['group_history_tables']}> Group Play History
-                            </label>
-                            <p class="help-block">Group play history for the same item and user as a single entry when progress is less than the watched percent.</p>
-                        </div>
                         <div class="checkbox advanced-setting">
                             <label>
                                 <input type="checkbox" id="history_table_activity" name="history_table_activity" value="1" ${config['history_table_activity']}> Current Activity in History Tables
@@ -227,6 +221,25 @@
                             </div>
                             <p class="help-block">Decide whether to use end credits markers to determine the 'watched' state of video items. When markers are not available the selected threshold percentage will be used.</p>
                         </div>
+                        <div class="checkbox advanced-setting">
+                            <label>
+                                <input type="checkbox" id="group_history_tables" name="group_history_tables" value="1" ${config['group_history_tables']}> Group Play History
+                            </label>
+                            <p class="help-block">Group play history for the same item and user as a single entry when progress is less than the watched percent.</p>
+                        </div>
+                        <div class="form-group advanced-setting">
+                            <label>Regroup Play History</label>
+                            <p class="help-block">
+                                Fix grouping of play history in the database.<br />
+                            </p>
+                            <div class="row">
+                                <div class="col-md-4">
+                                    <div class="btn-group">
+                                        <button class="btn btn-form" type="button" id="regroup_history">Regroup</button>
+                                    </div>
+                                </div>
+                            </div>
+                        </div>
                         <div class="form-group advanced-setting">
                             <label>Flush Temporary Sessions</label>
                             <p class="help-block">
@@ -2484,6 +2497,12 @@ $(document).ready(function() {
         confirmAjaxCall(url, msg);
     });
 
+    $("#regroup_history").click(function () {
+        var msg = 'Are you sure you want to regroup play history in the database?';
+        var url = 'regroup_history';
+        confirmAjaxCall(url, msg, null, 'Regrouping play history...');
+    });
+
     $("#delete_temp_sessions").click(function () {
         var msg = 'Are you sure you want to flush the temporary sessions?<br /><br /><strong>This will reset all currently active sessions.</strong>';
         var url = 'delete_temp_sessions';
diff --git a/plexpy/activity_processor.py b/plexpy/activity_processor.py
index 6851263b..b1558a56 100644
--- a/plexpy/activity_processor.py
+++ b/plexpy/activity_processor.py
@@ -709,7 +709,8 @@ class ActivityProcessor(object):
 
     def regroup_history(self):
         logger.info("Tautulli ActivityProcessor :: Creating database backup...")
-        database.make_backup()
+        if not database.make_backup():
+            return False
 
         logger.info("Tautulli ActivityProcessor :: Regrouping session history...")
 
@@ -720,6 +721,11 @@ class ActivityProcessor(object):
         results = self.db.select(query)
 
         for session in results:
-            self.group_history(session['id'], session)
+            try:
+                self.group_history(session['id'], session)
+            except Exception as e:
+                logger.error("Tautulli ActivityProcessor :: Error regrouping session history: %s", e)
+                return False
 
         logger.info("Tautulli ActivityProcessor :: Regrouping session history complete.")
+        return True
diff --git a/plexpy/webserve.py b/plexpy/webserve.py
index 72eb9170..06a9a802 100644
--- a/plexpy/webserve.py
+++ b/plexpy/webserve.py
@@ -51,6 +51,7 @@ if sys.version_info >= (3, 6):
 import plexpy
 if plexpy.PYTHON2:
     import activity_pinger
+    import activity_processor
     import common
     import config
     import database
@@ -85,6 +86,7 @@ if plexpy.PYTHON2:
         import macos
 else:
     from plexpy import activity_pinger
+    from plexpy import activity_processor
     from plexpy import common
     from plexpy import config
     from plexpy import database
@@ -434,6 +436,20 @@ class WebInterface(object):
             logger.warn("Unable to retrieve data for get_recently_added.")
             return serve_template(template_name="recently_added.html", data=None)
 
+    @cherrypy.expose
+    @cherrypy.tools.json_out()
+    @requireAuth(member_of("admin"))
+    @addtoapi()
+    def regroup_history(self, **kwargs):
+        """ Regroup play history in the database."""
+
+        result = activity_processor.ActivityProcessor().regroup_history()
+
+        if result:
+            return {'result': 'success', 'message': 'Regrouped play history.'}
+        else:
+            return {'result': 'error', 'message': 'Regrouping play history failed.'}
+
     @cherrypy.expose
     @cherrypy.tools.json_out()
     @requireAuth(member_of("admin"))