That sounds similar to this bug report.
http://bugzilla.xamarin.com/show_bug.cgi?id=202
On Tuesday, September 20, 2011 at 5:07, jowi [via MonoTouch] wrote:
> After a fresh installation of xcode 3.6 and Monodevelop 2.6 on a Mac Mini
> running Lion, i noticed that the iPhone/iPad simulator only starts
> automatically after the first (re)build/run command.
>
> If i change some code, (re)build and run the app, the simulator will not
> start the application again. From that moment i have to click on the
> simulator with the mouse to give it focus, and only then the app starts on
> the simulator. If i use debug in stead of run, the simulator does work every
> time.
>
> Anyone experienced this behaviour? On my not-so-legal vmware osx machine
> running Snow Leopard, the simulator works perfect and every time i run the
> app from monodevelop 2.6.
>
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