When navigating through context or drop-down menus containing sub-menus, hovering over the menu items can cause menus to show/hide during recording, but playback fails. This is because these hover events are not recorded by Squish.
At record-time, it is important that each menu item is explicitly clicked on, for an event to be properly recorded, including the first interaction with the menu bar. Reliable playback should be achievable this way.
Some context menus are not recordable or pickable, in which case, this link should help: