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Note that it is also possible to open two instances of Wing (with separate projects) - this can be very useful in some scenarios such as when your code consists of both a client and a server and you need to debug both or the interactions between them. This works best if you create two projects (e.g. one for client and one for server).
To do this on Windows - other platforms will differ right click on the task bar icon and select Wing from the pop-up menu.
You will be presented with a dialog telling you that the current project is going to be opened read only because it is locked by another instance but with a drop down option to open your other project.
Note that breakpoints, (and edit awareness), will only apply to the code that you are running from each specific window.
I would have screenshots but don't have the points to upload them yet - maybe later :-)