Context:
I have placed a breakpoint on the problem line, cleared output window, Press F10, compared the output when I run that line (adding an object to an ObservableCollection, whose CollectionChanged handler has code that loads up the unmanaged piece)
Case 1: Double-click on EXE.. which works perfectly (slightly snipped)
'MyApp.DesktopApp.exe': Loaded 'D:\WordAutomation\MyApp_Source\Executables\MyApp\ManagedFrameworkWrapper.dll', Symbols loaded.
'MyApp.DesktopApp.exe': Loaded 'D:\WordAutomation\MyApp_Source\Executables\MyApp\Unmanaged.Framework.dll'
'MyApp.DesktopApp.exe': Loaded 'C:\WINDOWS\WinSxS\x86_Microsoft.VC90.DebugCRT_1fc8b3b9a1e18e3b_9.0.21022.8_x-ww_597c3456\msvcr90d.dll', Symbols loaded.
'MyApp.DesktopApp.exe': Loaded 'C:\WINDOWS\WinSxS\x86_Microsoft.VC90.DebugCRT_1fc8b3b9a1e18e3b_9.0.21022.8_x-ww_597c3456\msvcp90d.dll', Symbols loaded.
'MyApp.DesktopApp.exe': Loaded 'C:\WINDOWS\WinSxS\x86_Microsoft.VC90.DebugMFC_1fc8b3b9a1e18e3b_9.0.21022.8_x-ww_2a62a75b\mfc90ud.dll', Symbols loaded.
'MyApp.DesktopApp.exe': Loaded 'C:\WINDOWS\system32\msimg32.dll'
'MyApp.DesktopApp.exe': Loaded 'D:\WordAutomation\MyApp_Source\Executables\MyApp\HelperFunctions.dll'
'MyApp.DesktopApp.exe': Loaded 'C:\WINDOWS\system32\dbghelp.dll'
'MyApp.DesktopApp.exe': Loaded 'C:\WINDOWS\WinSxS\x86_Microsoft.VC90.DebugCRT_1fc8b3b9a1e18e3b_9.0.21022.8_x-ww_597c3456\msvcm90d.dll', Symbols loaded.
'MyApp.DesktopApp.exe': Loaded 'C:\WINDOWS\WinSxS\x86_Microsoft.VC90.MFCLOC_1fc8b3b9a1e18e3b_9.0.21022.8_x-ww_11f3ea3a\mfc90enu.dll', Binary was not built with debug information.
CCollectionDataType ConstCCollectionDataType ConstCCollectionDataType ConstCCollectionDataType ConstCCollectionDataType ConstCCollectionDataType Const'MyApp.DesktopApp.exe' (Managed): Loaded 'D:\WordAutomation\MyApp_Source\Executables\MyApp\ManagedFrameworkWrapper.dll', Symbols loaded.
'MyApp.DesktopApp.exe' (Managed): Loaded 'C:\WINDOWS\WinSxS\x86_Microsoft.VC90.DebugCRT_1fc8b3b9a1e18e3b_9.0.21022.8_x-ww_597c3456\msvcm90d.dll', Symbols loaded.
The thread 'Win32 Thread' (0x12ec) has exited with code 0 (0x0).
Case 2: Run the same line, but launched from within a Word code-behind .cs file
A first chance exception of type 'System.IO.FileNotFoundException' occurred in WindowsBase.dll
The program '[5320] WINWORD.EXE: Managed' has exited with code 0 (0x0).
I have tried
I notice that Word seems to be copying over the managed ref assemblies to a location as shown in below snippet.. which may be a line of investigation. But why is word doing this and how does it resolve unmanaged DLLs.. I don't know. Also in the first snippet, there are some DLLs loaded from a WinSXS path, that could also be another lead.
'WINWORD.EXE' (Managed): Loaded 'C:\Documents and Settings\pillaigi\Local Settings\Application Data\assembly\dl3\6HQYB5GK.LY0\KC4WN109.HT4\4d81c901\70abeb86_124ec901\MyWPFPlotPopup.DLL', Symbols loaded.
Finally to close off gracefully... Help!!
To find out what dll is causing the problem and where the dll is being looked for use ProcessMon (free from sysinternals).
See my answer here: Referenced answer