Apparently if you check the first box “show all filename extensions” you cannot debug your iOS apps in the simulator.
Took me some time to figure that one out.
Don’t get caught.
Did everyone except me already know this?
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This makes absolutely no sense to me. How did you discover it? Is there a thread somewhere like Apple or StackOverflow that you found?
Ha! This fixes the issue we’ve been trying to track down forever now.
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Well huh. He’s correct. This seems to be related to <https://xojo.com/issue/64582> for M1 users. Now, I always show file extensions, and Xcode can build to the simulator with file extensions showing. But hopefully it helps the engineers discover the issue with Xojo. Awesome!
Case updated.
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I had literally changed that this am and then looking at the console it just popped into my head. I could have easily overlooked it. Fluke.
But… phew… only lost 3 hours!
Fantastic!
Your three hours, a bunch of us have been trying to figure this one out for…what…months? Haha. Excellent work.
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Pure luck. I didn’t realize others were struggling with it.
Now I feel good for sharing. Nice way to end the week.
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There have been discussions… and testing… and clean installs… and you come along and click a checkbox… 
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Guys, I was having a really crappy day. Hearing I In any way contributed to you overcoming an issue makes my day.
Thanks for letting me know it helped.
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Excellent Find Chris! Now we have an internal reproducible case!
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My first thought was, “no way that’s true, someone else needs to test this.” Good thing I’m not in charge of these things. 
Nice find @Chris_Halford.
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Wow, you mean there are developers who DON’T change this preference as nearly one of the first things to do on a new install? I’ve always detested this default in both Windows and macOS.
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You, sir, are a legend.
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I’ve always assumed that most developers have file extensions showing. I can’t imagine working with them hidden!
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Personally I’m more of a visual guy and as such rely on the icons more so than the extensions. When I want an extension for a file, I tend to turn it on for that particular case.
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I have been surprised a few times, when loading a file and it wasn’t what I thought. Like a pdf vs png. I. like to see both picture and extension - but in general I agree with you. I am part of an extremely visual industry… we all like pictures.
I mean it’s general computer safety to have extensions on.
Launching the wrong item that looks correct is how people launch malware.
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And to me, having the extension visible makes me a visual guy. I like seeing it in the filename – and that is without the malware considerations that @Tim_Parnell references.
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Thanks a bunch! Finally can use the debugger. Note though that it appears to show or hide the extension .app. Example: Pdf files still show their extension when turning show all… off. So not checking, it seems to alleviate the general concern that it would hold for all files.