diff --git a/orangecanvas/document/interactions.py b/orangecanvas/document/interactions.py
index 507c22d4..a94b42d6 100644
--- a/orangecanvas/document/interactions.py
+++ b/orangecanvas/document/interactions.py
@@ -116,6 +116,7 @@ def __init__(self, document, parent=None, deleteOnEnd=True):
         self.deleteOnEnd = deleteOnEnd
 
         self.cancelOnEsc = False
+        self.extendedOnShift = False
 
         self.__finished = False
         self.__canceled = False
@@ -1415,6 +1416,9 @@ def mouseReleaseEvent(self, event):
                 p1, p2 = map(self.arrow_item.mapFromScene, (p1, p2))
                 self.arrow_item.setLine(QLineF(p1, p2))
 
+            if event.modifiers() & Qt.ShiftModifier:
+                self.extendedOnShift = True
+
             self.end()
             return True
         else:
diff --git a/orangecanvas/document/schemeedit.py b/orangecanvas/document/schemeedit.py
index 5a2f60ba..91019d6b 100644
--- a/orangecanvas/document/schemeedit.py
+++ b/orangecanvas/document/schemeedit.py
@@ -1913,7 +1913,7 @@ def __toggleNewArrowAnnotation(self, checked):
             handler = self.__scene.user_interaction_handler
             if isinstance(handler, interactions.NewArrowAnnotation):
                 # Cancel the interaction and restore the state
-                handler.ended.disconnect(action.toggle)
+                handler.ended.disconnect(self.__toggleNewArrowAction)
                 handler.cancel(interactions.UserInteraction.UserCancelReason)
                 log.info("Canceled new arrow annotation")
 
@@ -1922,10 +1922,18 @@ def __toggleNewArrowAnnotation(self, checked):
             checked_action = self.__arrowColorActionGroup.checkedAction()
             handler.setColor(checked_action.data())
 
-            handler.ended.connect(action.toggle)
+            handler.ended.connect(self.__toggleNewArrowAction)
 
             self._setUserInteractionHandler(handler)
 
+    def __toggleNewArrowAction(self):
+        handler = self.sender()
+        action = self.__newArrowAnnotationAction
+        action.toggle()  # end current
+        if handler.extendedOnShift:
+            handler.extendedOnShift = False  # clear shift flag
+            action.toggle()  # start new
+
     def __onFontSizeTriggered(self, action):
         # type: (QAction) -> None
         if not self.__newTextAnnotationAction.isChecked():