LIstbox has drag operation performed with DragDropManager. AllowDrag = True and DragVisual set on DragInitialize. RadToolTipService sets ToolTip for element in the ItemTemplate of the ListBox (for example TextBlock). While tooltip is open , dragging from listbox results in 2 issues: - tooltip is not properly closed - tooltip cannot be shown anymore on the listboxitems A possible workaround is to set telerik:DragDropManager.AllowCapturedDrag = True on the element which has RadToolTip.ToolTipContent set on itself.