Luke,
Sounds like you have a mouseEvent listener attached to the map that is preventing the right click context menu from receiving the event (just a guess).
Luke,
I think the featurelayer that has the context menu listener, but I would see if you have a map mouse listener attached that is preventing the graphics from receiving the event. Or do you have a widget that is firing a setMapAction as that by default sets the mouse events to not listen, until the drawtool is deactivated.
Luke,
It depends. I think that the DrawTool disables or removes all listeners when it is activated by default, unless you choose to add it's addition argument of false.
drawTool.activate(tool);and change it to
drawTool.activate(tool, true);and see if that makes a difference. Also search your custom code for things that add event listeners to the map or graphics.