Although DiagramControl doesn't provide such a feature out of the box, you can implement it manually. For this, calculate intersections between items and connectors. I suggest that you use the ShapeIntersectionHelper.GetIntersectionPoints method for this purpose. If the collection of intersections is not empty, create a new connector and attach the dragged shape to the existing and newly created connectors. I have attached a sample project to illustrate the main idea of this approach.