Under Windows we seem to have an issue where the Insert menu stops working Feedback Case #50157. This means you have to close down the IDE and reopen everything. While this might seem like a minor inconvenience its really jarring when you're in a good flow, you have your set up just as you want it and all the projects open that you're working on.
Maybe some additional logging could be put into the Windows version to actually see what is failing when we click something on the Insert menu and it does literally nothing.
Bookmark this thread, If you see this happen, just post below "Happened again" and someone might actually look into the problem when they see how often if happens to us.