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For legacy application support reasons at my company, our Mac build host (OSX El Capitan) has multiple versions of xcode installed.
One is version 6.4 and located at /Applications/Xcode.app.
The other is version 7.3.1 and located at /Applications/xcode731/Xcode.app.
My Xamarin visual studio settings point the Xcode directory to use to /Applications/xcode731/Xcode.app.
When launching the app with the "remote to Windows" box unchecked, everything runs perfectly and appears on the simulator on the Mac as expected.
When the box is checked, I consistently get the "failed to install" error message. Unchecking the box and redeploying to the normal simulator, then checking the box again does not resolve this.
I found out by running "xcode-select-p" on the Mac that the command line tools version being used by default was at /Applications/Xcode.app/Contents/Developer (the 6.4 version).
I ran "xcode-select -switch /Applications/xcode731/Xcode.app/Contents/Developer" under an admin account to switch the default command line tools to be the 7.3.1 version. After doing this, the remote simulator to Windows works as expected (and when switching back to the 6.4 version once again does not work).
I would expect that the Xcode path indicated in the Visual Studio settings would dictate which version of the command line tools to use, i.e. the version of the command line tools that corresponds to the indicated xcode path should always be the version the remote simulator uses regardless of the machine's defaults.
It should be using the Visual Studio settings path, and then if there's nothing set there it will fall back to xcode-select.
Can you attach your server logs from an instance of the VS settings not matching xcode-select? You'll find them at ~/Library/Logs/Xamarin/Simulator.Server
*** Bug 53943 has been marked as a duplicate of this bug. ***
Internal reproduction discovered, fixing.
I'm not sure how I missed your first reply, but sorry for not responding with the logs earlier. Glad you were able to reproduce and thanks in advance!
This is fixed in 1.0.2
*** Bug 54046 has been marked as a duplicate of this bug. ***