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Visual Studio iOS Debug Build Failure

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Good day everyone,

I've been unsuccessfully trying, for some time now, to solve issues I am facing with building iOS applications from Visual Studio. I've done a great deal of searching, in these forums and the broader internet, and have found a number of seemingly related problems but not a solution to this one in particular. That said, if I have missed something obvious, I apologise.

To the matter at hand, I am unable to start applications with 'Enabled Debugging' selected in the iOS build configuration panel. That is to say, the (or any valid) application will successfully deploy to, and run on, a device or emulator when the 'Release' configuration is selected or if the 'Debug' configuration is modified by unchecking the 'Enabled Debugging' option. Similarly, the same application (with only the reference paths changed as necessary) will successfully deploy to, and run on, a device or emulator with full debugging support from Xamarin Studio on the Mac.

In short, the issue seems isolated to the 'Enable Debugging' option. I have encountered the same outcome with Xamarin samples, templates from third parties, and with my own projects. The problem has persisted in the face of physically resetting hardware, repairing with the server and resetting content and settings on the simulator.

On the Visual Studio side I am simply informed that 'There were deployment errors.' In the case of the 'AnalogClock' sample, the output displays:

2>Target "_BuildNativeApplication" in file "C:\Program Files (x86)\MSBuild\Xamarin\iOS\Xamarin.MonoTouch.Common.targets" from project "D:\User Data\Visual Studio 2012\Projects\Xamarin Samples\Analog Clock\AnalogClock.iOS\AnalogClock.iOS.csproj" (target "_RemoteBuild" depends on it):
2>Server command 'Build': application remote build failed
2>Command execution task ended with exception
2>Exception System.Net.WebException: The remote server returned an error: (500) Internal Server Error.
2>Exception details can be found in the log file
2>
2>
2>Remote build step failed.
2>Done building target "_BuildNativeApplication" in project "AnalogClock.iOS.csproj" -- FAILED.
2>Done building project "AnalogClock.iOS.csproj" -- FAILED.
2>Build FAILED.

The mtbserver.log file is a little more helpful and detailed. The problem section, in the same example, appears to be:

06-Apr-2014 00:14:42] Starting pdb2mdb "AnalogClockiOS.exe"
[06-Apr-2014 00:14:42] Exception: Exception type: System.ComponentModel.Win32Exception
ApplicationName='pdb2mdb', CommandLine='"AnalogClockiOS.exe"', CurrentDirectory='/Users/Nathan/Library/Caches/Xamarin/mtbs/builds/AnalogClockiOS/69dc2865-6bff-4172-857f-64da4787a033/assemblies', Native error= Cannot find the specified file
  at System.Diagnostics.Process.Start_noshell (System.Diagnostics.ProcessStartInfo startInfo, System.Diagnostics.Process process) [0x00000] in <filename unknown>:0 
  at System.Diagnostics.Process.Start_common (System.Diagnostics.ProcessStartInfo startInfo, System.Diagnostics.Process process) [0x00000] in <filename unknown>:0 
  at System.Diagnostics.Process.Start () [0x00000] in <filename unknown>:0 
  at (wrapper remoting-invoke-with-check) System.Diagnostics.Process:Start ()
  at MonoTouch.Tools.Tools.ToolBase.RunInner (MonoTouch.Tools.Tools.RunInfo ri) [0x00000] in <filename unknown>:0 
[06-Apr-2014 00:14:42] Command [Build: CommmandUrl=Build] finished (32)
[06-Apr-2014 00:14:42] Error: Application not connected, cannot establish logging connection with VS
[06-Apr-2014 00:14:42] Error: Application not connected, cannot establish debugger connection with VS
[06-Apr-2014 00:14:42] Command [DebugApplication: CommmandUrl=DebugApplication] finished (22)

The specific file that cannot be found obviously varies between projects. In this case it's an/the executable, in the case of the project I am most interested in getting to work it is the alphabetically first of the referenced assemblies. The exception is the same in each case, however. I find it very puzzling that this only occurs with debugging enabled. Any help would certainly be appreciated.

Additional Information:

Windows OS: Windows 8.1
Visual Studio Version: 12.030110.00 Update 1
.Net Framework Version: 4.5.51641
Windows Xamarin.iOS Extension Version: 1.10.47
Mac Xamarin iOS Version: 7.2.0.2

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