diff --git a/src/calibre/gui2/tweak_book/boss.py b/src/calibre/gui2/tweak_book/boss.py
index a99761940c..b8fe7bdb1d 100644
--- a/src/calibre/gui2/tweak_book/boss.py
+++ b/src/calibre/gui2/tweak_book/boss.py
@@ -1102,6 +1102,8 @@ class Boss(QObject):
         self.apply_current_editor_state()
         if is_modified:
             self.set_modified()
+            self.global_undo.truncate()
+            self.update_global_history_actions()
     # }}}
 
     def apply_current_editor_state(self):
diff --git a/src/calibre/gui2/tweak_book/undo.py b/src/calibre/gui2/tweak_book/undo.py
index 1fbfb02246..f67fedc735 100644
--- a/src/calibre/gui2/tweak_book/undo.py
+++ b/src/calibre/gui2/tweak_book/undo.py
@@ -81,13 +81,7 @@ class GlobalUndoHistory(QAbstractListModel):
         self.pos = 0
         self.reset()
 
-    def add_savepoint(self, new_container, message):
-        try:
-            self.states[self.pos].rewind_message = self.states[self.pos].message
-            self.states[self.pos].message = message
-        except IndexError:
-            raise IndexError('The checkpoint stack has an incorrect position pointer. This should never happen: self.pos = %r, len(self.states) = %r' % (
-                self.pos, len(self.states)))
+    def truncate(self):
         extra = self.states[self.pos+1:]
         if extra:
             self.beginRemoveRows(ROOT, self.pos+1, len(self.states) - 1)
@@ -95,6 +89,15 @@ class GlobalUndoHistory(QAbstractListModel):
         self.states = self.states[:self.pos+1]
         if extra:
             self.endRemoveRows()
+
+    def add_savepoint(self, new_container, message):
+        try:
+            self.states[self.pos].rewind_message = self.states[self.pos].message
+            self.states[self.pos].message = message
+        except IndexError:
+            raise IndexError('The checkpoint stack has an incorrect position pointer. This should never happen: self.pos = %r, len(self.states) = %r' % (
+                self.pos, len(self.states)))
+        self.truncate()
         self.beginInsertRows(ROOT, self.pos+1, self.pos+1)
         self.states.append(State(new_container))
         self.pos += 1