when run "mono Fiddler.exe", i am getting below error, any idea?
WARNING: The Carbon driver has not been ported to 64bits, and very few parts of Windows.Forms will work properly, or at all
exception inside UnhandledException handler: The type initializer for 'Fiddler.CONFIG' threw an exception.
[ERROR] FATAL UNHANDLED EXCEPTION: System.TypeInitializationException: The type initializer for 'System.Windows.Forms.WindowsFormsSynchronizationContext' threw an exception. ---> System.TypeInitializationException: The type initializer for 'System.Windows.Forms.ThemeEngine' threw an exception. ---> System.TypeInitializationException: The type initializer for 'System.Windows.Forms.ThemeWin32Classic' threw an exception. ---> System.TypeInitializationException: The type initializer for 'System.Drawing.KnownColors' threw an exception. ---> System.TypeInitializationException: The type initializer for 'System.Drawing.GDIPlus' threw an exception. ---> System.DllNotFoundException: libgdiplus.dylib
at (wrapper managed-to-native) System.Drawing.GDIPlus:GdiplusStartup (ulong&,System.Drawing.GdiplusStartupInput&,System.Drawing.GdiplusStartupOutput&)
at System.Drawing.GDIPlus..cctor () <0x109dba840 + 0x001d5> in <filename unknown>:0
--- End of inner exception stack trace ---
at System.Drawing.KnownColors..cctor () <0x109dba5a0 + 0x00064> in <filename unknown>:0
--- End of inner exception stack trace ---
at System.Drawing.Color.get_Black () <0x10a8ca4e0 + 0x0001e> in <filename unknown>:0
at System.Windows.Forms.ThemeWin32Classic..cctor () <0x10a8ca3d0 + 0x00015> in <filename unknown>:0
--- End of inner exception stack trace ---
at System.Windows.Forms.ThemeVisualStyles..ctor () <0x10a8ca2f0 + 0x00014> in <filename unknown>:0
at System.Windows.Forms.ThemeEngine..cctor () <0x10a8ca1d0 + 0x0008f> in <filename unknown>:0
--- End of inner exception stack trace ---
at System.Windows.Forms.SystemInformation.get_MenuAccessKeysUnderlined () <0x10a8c9da0 + 0x00010> in <filename unknown>:0
at System.Windows.Forms.Control..ctor () <0x10a8c86e0 + 0x00288> in <filename unknown>:0
at (wrapper remoting-invoke-with-check) System.Windows.Forms.Control:.ctor ()
at System.Windows.Forms.WindowsFormsSynchronizationContext..cctor () <0x10a8c9c90 + 0x00031> in <filename unknown>:0
--- End of inner exception stack trace ---
at System.Windows.Forms.Control..ctor () <0x10a8c86e0 + 0x0005e> in <filename unknown>:0
at System.Windows.Forms.ScrollableControl..ctor () <0x10a8c8080 + 0x00017> in <filename unknown>:0
at System.Windows.Forms.ContainerControl..ctor () <0x10a8c7ea0 + 0x0002d> in <filename unknown>:0
at System.Windows.Forms.Form..ctor () <0x10a8c7510 + 0x000f9> in <filename unknown>:0
at ...ctor () <0x10a8c5080 + 0x0002d> in <filename unknown>:0
at (wrapper remoting-invoke-with-check) .:.ctor ()
at Fiddler.frmViewer. (System.String[] ) <0x109db3870 + 0x00136> in <filename unknown>:0
at Fiddler.frmViewer. (System.String[] ) <0x109db2da0 + 0x0009b> in <filename unknown>:0
16 Answers, 1 is accepted
It looks like you have a custom built 64-bit Mono version. Is that the case? Mono still doesn't offer support for WinForms in their 64-bit implementation and that is why you get this exception. You will have to switch to 32-bit mono to run Fiddler.
Regards,
Tsviatko Yovtchev
Telerik by Progress


http://www.mono-project.com/download/#download-mac
I miss Fiddler :(
You are right - there is no installer for 32-bit version of Mono. But there seems to be a switch, which can be used to run an assembly on the 32-bit Mono VM. You can find more information here.
Regards,
Alexander
Progress Telerik

Hi Alexander,
Can you give specifics on how to change mono from 64 bit to 32 bit? The steps were not clear in the link you provided. I am very new to MAC's and using this MAC, including the steps of installing mono to use Fiddler for my testing has been a google search. By new, I am learning how to navigate Finder and just started with the Terminal today and Fiddler is my 3rd program manually installed. Any extra help is appreciated.
Cheers,
Andy

Alexander,
I typed in "mono --arch=32" in a terminal. When I do I get a list of commands.
Andrews-MBP-2:fiddler-mac searsa$ mono --arch=32
Usage is: mono [options] program [program-options]
Development:
--aot[=<options>] Compiles the assembly to native code
--debug[=<options>] Enable debugging support, use --help-debug for details
--debugger-agent=options Enable the debugger agent
--profile[=profiler] Runs in profiling mode with the specified profiler module
--trace[=EXPR] Enable tracing, use --help-trace for details
--jitmap Output a jit method map to /tmp/perf-PID.map
--help-devel Shows more options available to developers
Runtime:
--config FILE Loads FILE as the Mono config
--verbose, -v Increases the verbosity level
--help, -h Show usage information
--version, -V Show version information
--runtime=VERSION Use the VERSION runtime, instead of autodetecting
--optimize=OPT Turns on or off a specific optimization
Use --list-opt to get a list of optimizations
--security[=mode] Turns on the unsupported security manager (off by default)
mode is one of cas, core-clr, verifiable or validil
--attach=OPTIONS Pass OPTIONS to the attach agent in the runtime.
Currently the only supported option is 'disable'.
--llvm, --nollvm Controls whenever the runtime uses LLVM to compile code.
--gc=[sgen,boehm] Select SGen or Boehm GC (runs mono or mono-sgen)
--arch=[32,64] Select architecture (runs mono32 or mono64)
--handlers Install custom handlers, use --help-handlers for details.
--aot-path=PATH List of additional directories to search for AOT images.
The command you should use is
mono --arch=32 Fiddler.exe
This will run Fiddler in a 32-bit Mono.
Regards,
Alexander
Progress Telerik

When I tried to switch to mono32, it failed too:
$ mono --arch=32
Error: --arch=32 Failed to switch to 'mono32'.
Hey qingqing,
The above command tells the mono to run the application as a 32-bit app, while the modern macOS versions no longer support 32-bit architecture. That said, the Fiddler Mono builds are no longer officially supported, but you could try Fiddler Everywhere, which comes with official support for macOS, WIndows, and Linux distributions.



mono --arch=32 Fiddler.exe

I had some troubles so did a walk through and posted it here. I ran in to the ARCH issue and accepting the eula for Mono: https://blogs.msdn.microsoft.com/jpsanders/2018/02/08/usinginstalling-fiddler-on-mac-os/


Hi,
Tried everything mentioned but still ran out of options !!!
GSBNG-C02VV0DTG8WN:~ avkbabu$ mono /Users/avkbabu/Documents/fiddler-mac/fiddler.exe
WARNING: The Carbon driver has not been ported to 64bits, and very few parts of Windows.Forms will work properly, or at all
Fontconfig warning: ignoring UTF-8: not a valid region tag
Fontconfig warning: ignoring UTF-8: not a valid region tag
Fontconfig warning: ignoring UTF-8: not a valid region tag
Fontconfig warning: ignoring UTF-8: not a valid region tag
Fontconfig warning: ignoring UTF-8: not a valid region tag
Fontconfig warning: ignoring UTF-8: not a valid region tag
Fontconfig warning: ignoring UTF-8: not a valid region tag
Stacktrace:
at <unknown> <0xffffffff>
at (wrapper managed-to-native) System.Windows.Forms.XplatUICarbon.CGDisplayBounds (intptr) [0x00002] in <1141838629e74c21a3b96d0a06337bad>:0
at System.Windows.Forms.XplatUICarbon.get_WorkingArea () [0x00005] in <1141838629e74c21a3b96d0a06337bad>:0
at System.Windows.Forms.XplatUICarbon.get_VirtualScreen () [0x00000] in <1141838629e74c21a3b96d0a06337bad>:0
at System.Windows.Forms.XplatUI.get_VirtualScreen () [0x00000] in <1141838629e74c21a3b96d0a06337bad>:0
at System.Windows.Forms.Screen..cctor () [0x00034] in <1141838629e74c21a3b96d0a06337bad>:0
at (wrapper runtime-invoke) object.runtime_invoke_void (object,intptr,intptr,intptr) [0x0001e] in <ede5cf6930dc4b9a8366f15f6c89bbd0>:0
at <unknown> <0xffffffff>
at System.Windows.Forms.Form.get_CreateParams () [0x00157] in <1141838629e74c21a3b96d0a06337bad>:0
at System.Windows.Forms.Control.CreateHandle () [0x0002a] in <1141838629e74c21a3b96d0a06337bad>:0
at System.Windows.Forms.Form.CreateHandle () [0x00000] in <1141838629e74c21a3b96d0a06337bad>:0
at System.Windows.Forms.Control.CreateControl () [0x00039] in <1141838629e74c21a3b96d0a06337bad>:0
at System.Windows.Forms.Control.SetVisibleCore (bool) [0x0003a] in <1141838629e74c21a3b96d0a06337bad>:0
at System.Windows.Forms.Form.SetVisibleCore (bool) [0x00065] in <1141838629e74c21a3b96d0a06337bad>:0
at System.Windows.Forms.Control.set_Visible (bool) [0x00009] in <1141838629e74c21a3b96d0a06337bad>:0
at System.Windows.Forms.Control.Show () [0x00000] in <1141838629e74c21a3b96d0a06337bad>:0
at (wrapper remoting-invoke-with-check) System.Windows.Forms.Control.Show () [0x00031] in <1141838629e74c21a3b96d0a06337bad>:0
at Fiddler.frmViewer. (string[]) [0x00081] in <09623c708fdb40a483cea147bbea7a7f>:0
at Fiddler.frmViewer. (string[]) [0x00016] in <09623c708fdb40a483cea147bbea7a7f>:0
at (wrapper runtime-invoke) <Module>.runtime_invoke_void_object (object,intptr,intptr,intptr) [0x0004e] in <09623c708fdb40a483cea147bbea7a7f>:0
Native stacktrace:
0 mono 0x000000010bb4cc01 mono_handle_native_crash + 257
1 mono 0x000000010bbb7236 altstack_handle_and_restore + 70
2 SkyLight 0x00007fff6aa42fa8 SLDisplayBounds + 83
3 ??? 0x0000000112cd08de 0x0 + 4610394334
4 ??? 0x000000010c522486 0x0 + 4501677190
5 mono 0x000000010baa34c7 mono_jit_runtime_invoke + 1383
6 mono 0x000000010bc63ed4 do_runtime_invoke + 84
7 mono 0x000000010bc60024 mono_runtime_class_init_full + 996
8 mono 0x000000010ba9c7ce mono_jit_compile_method_inner + 2478
9 mono 0x000000010ba9f683 mono_jit_compile_method_with_opt + 1363
10 mono 0x000000010bb4f0c1 common_call_trampoline + 1217
11 mono 0x000000010bb4ebbc mono_magic_trampoline + 60
12 ??? 0x000000010bf6639e 0x0 + 4495664030
13 ??? 0x000000010edf2b4b 0x0 + 4544473931
14 ??? 0x000000010c7fbb7f 0x0 + 4504664959
15 ??? 0x000000010c7fb7f7 0x0 + 4504664055
16 ??? 0x000000010c522043 0x0 + 4501676099
17 mono 0x000000010baa34c7 mono_jit_runtime_invoke + 1383
18 mono 0x000000010bc63ed4 do_runtime_invoke + 84
19 mono 0x000000010bc674f9 do_exec_main_checked + 137
20 mono 0x000000010bb104bf mono_jit_exec + 287
21 mono 0x000000010bb12cb4 mono_main + 9140
22 mono 0x000000010ba92e8d main + 253
23 mono 0x000000010ba92d84 start + 52
24 ??? 0x0000000000000002 0x0 + 2
Debug info from gdb:
(lldb) command source -s 0 '/tmp/mono-gdb-commands.HaOWSg'
Executing commands in '/tmp/mono-gdb-commands.HaOWSg'.
(lldb) process attach --pid 30527
warning: (x86_64) /Library/Frameworks/Mono.framework/Versions/5.8.0/lib/mono/4.5/mscorlib.dll.dylib empty dSYM file detected, dSYM was created with an executable with no debug info.
warning: (x86_64) /Library/Frameworks/Mono.framework/Versions/5.8.0/lib/libglib-2.0.0.dylib empty dSYM file detected, dSYM was created with an executable with no debug info.
Process 30527 stopped
* thread #1, name = 'tid_307', queue = 'com.apple.main-thread', stop reason = signal SIGSTOP
frame #0: 0x00007fff709e3502 libsystem_kernel.dylib`__wait4 + 10
libsystem_kernel.dylib`__wait4:
-> 0x7fff709e3502 <+10>: jae 0x7fff709e350c ; <+20>
0x7fff709e3504 <+12>: movq %rax, %rdi
0x7fff709e3507 <+15>: jmp 0x7fff709da0dd ; cerror
0x7fff709e350c <+20>: retq
Target 0: (mono) stopped.
Executable module set to "/Library/Frameworks/Mono.framework/Home/bin/mono".
Architecture set to: x86_64h-apple-macosx.
(lldb) thread list
Process 30527 stopped
* thread #1: tid = 0x2a6e13, 0x00007fff709e3502 libsystem_kernel.dylib`__wait4 + 10, name = 'tid_307', queue = 'com.apple.main-thread', stop reason = signal SIGSTOP
thread #2: tid = 0x2a6e18, 0x00007fff709e2cee libsystem_kernel.dylib`__psynch_cvwait + 10, name = 'SGen worker'
thread #3: tid = 0x2a6e1b, 0x00007fff709d97fe libsystem_kernel.dylib`semaphore_wait_trap + 10, name = 'Finalizer'
thread #4: tid = 0x2a6e1c, 0x00007fff709e3562 libsystem_kernel.dylib`__workq_kernreturn + 10
thread #5: tid = 0x2a6e1d, 0x00007fff709e3562 libsystem_kernel.dylib`__workq_kernreturn + 10
thread #6: tid = 0x2a6e32, 0x00007fff709e3562 libsystem_kernel.dylib`__workq_kernreturn + 10
thread #7: tid = 0x2a6e41, 0x00007fff709e2cee libsystem_kernel.dylib`__psynch_cvwait + 10, name = 'Timer-Scheduler'
(lldb) thread backtrace all
* thread #1, name = 'tid_307', queue = 'com.apple.main-thread', stop reason = signal SIGSTOP
* frame #0: 0x00007fff709e3502 libsystem_kernel.dylib`__wait4 + 10
frame #1: 0x000000010bb4cc8e mono`mono_handle_native_crash(signal=<unavailable>, ctx=<unavailable>, info=<unavailable>) at mini-exceptions.c:2731 [opt]
frame #2: 0x000000010bbb7236 mono`altstack_handle_and_restore(ctx=0x00007ffee416e490, obj=0x0000000000000000, stack_ovf=0) at exceptions-amd64.c:856 [opt]
frame #3: 0x00007fff6aa42fa8 SkyLight`SLDisplayBounds + 83
frame #4: 0x0000000112cd08de
frame #5: 0x000000010c522486
frame #6: 0x000000010baa34c7 mono`mono_jit_runtime_invoke(method=<unavailable>, obj=<unavailable>, params=0x0000000000000000, exc=0x0000000112cd0260, error=<unavailable>) at mini-runtime.c:2800 [opt]
frame #7: 0x000000010bc63ed4 mono`do_runtime_invoke(method=0x00007f81d40cf748, obj=0x0000000000000000, params=0x0000000000000000, exc=0x00007ffee416eb88, error=0x00007ffee416ed60) at object.c:2849 [opt]
frame #8: 0x000000010bc60024 mono`mono_runtime_class_init_full [inlined] mono_runtime_try_invoke(method=<unavailable>, obj=<unavailable>, params=<unavailable>, error=0x00007ffee416ed60) at object.c:2956 [opt]
frame #9: 0x000000010bc5ffdf mono`mono_runtime_class_init_full(vtable=0x00007f81d413bbf0, error=0x00007ffee416ed60) at object.c:473 [opt]
frame #10: 0x000000010ba9c7ce mono`mono_jit_compile_method_inner(method=0x00007f81d40cf5d0, target_domain=<unavailable>, opt=<unavailable>, error=0x00007ffee416ed60) at mini.c:4343 [opt]
frame #11: 0x000000010ba9f683 mono`mono_jit_compile_method_with_opt(method=0x00007f81d40cf5d0, opt=<unavailable>, jit_only=0, error=<unavailable>) at mini-runtime.c:2129 [opt]
frame #12: 0x000000010bb4f0c1 mono`common_call_trampoline(regs=0x00007ffee416ee28, code="H\x8b?H??\xa8H\x8b??8, m=0x00007f81d40cf5d0, vt=<unavailable>, vtable_slot=<unavailable>, error=<unavailable>) at mini-trampolines.c:715 [opt]
frame #13: 0x000000010bb4ebbc mono`mono_magic_trampoline(regs=0x00007ffee416ee28, code="H\x8b?H??\xa8H\x8b??8, arg=0x00007f81d40cf5d0, tramp=<unavailable>) at mini-trampolines.c:846 [opt]
frame #14: 0x000000010bf6639e
frame #15: 0x000000010edf2b4b
frame #16: 0x000000010c7fbb7f
frame #17: 0x000000010c7fb7f7
frame #18: 0x000000010c522043
frame #19: 0x000000010baa34c7 mono`mono_jit_runtime_invoke(method=<unavailable>, obj=<unavailable>, params=0x00007ffee416f698, exc=0x000000010c852548, error=<unavailable>) at mini-runtime.c:2800 [opt]
frame #20: 0x000000010bc63ed4 mono`do_runtime_invoke(method=0x00007f81d2700528, obj=0x0000000000000000, params=0x00007ffee416f698, exc=0x0000000000000000, error=0x00007ffee416f6d8) at object.c:2849 [opt]
frame #21: 0x000000010bc674f9 mono`do_exec_main_checked [inlined] mono_runtime_invoke_checked(method=<unavailable>, obj=<unavailable>, error=<unavailable>) at object.c:3002 [opt]
frame #22: 0x000000010bc674b8 mono`do_exec_main_checked(method=0x00007f81d2700528, args=<unavailable>, error=0x00007ffee416f6d8) at object.c:4726 [opt]
frame #23: 0x000000010bb104bf mono`mono_jit_exec(domain=<unavailable>, assembly=<unavailable>, argc=1, argv=0x00007ffee416f9f8) at driver.g.c:1040 [opt]
frame #24: 0x000000010bb12cb4 mono`mono_main [inlined] main_thread_handler at driver.g.c:1109 [opt]
frame #25: 0x000000010bb12c81 mono`mono_main(argc=2, argv=<unavailable>) at driver.g.c:2222 [opt]
frame #26: 0x000000010ba92e8d mono`main [inlined] mono_main_with_options(argc=<unavailable>, argv=<unavailable>) at main.c:46 [opt]
frame #27: 0x000000010ba92e79 mono`main(argc=2, argv=<unavailable>) at main.c:339 [opt]
frame #28: 0x000000010ba92d84 mono`start + 52
thread #2, name = 'SGen worker'
frame #0: 0x00007fff709e2cee libsystem_kernel.dylib`__psynch_cvwait + 10
frame #1: 0x00007fff70b1f662 libsystem_pthread.dylib`_pthread_cond_wait + 732
frame #2: 0x000000010bd1cc9e mono`thread_func [inlined] mono_os_cond_wait(mutex=<unavailable>) at mono-os-mutex.h:173 [opt]
frame #3: 0x000000010bd1cc8b mono`thread_func at sgen-thread-pool.c:165 [opt]
frame #4: 0x000000010bd1cc7d mono`thread_func(data=0x0000000000000000) at sgen-thread-pool.c:196 [opt]
frame #5: 0x00007fff70b1e6c1 libsystem_pthread.dylib`_pthread_body + 340
frame #6: 0x00007fff70b1e56d libsystem_pthread.dylib`_pthread_start + 377
frame #7: 0x00007fff70b1dc5d libsystem_pthread.dylib`thread_start + 13
thread #3, name = 'Finalizer'
frame #0: 0x00007fff709d97fe libsystem_kernel.dylib`semaphore_wait_trap + 10
frame #1: 0x000000010bcc941c mono`finalizer_thread [inlined] mono_os_sem_wait(flags=MONO_SEM_FLAGS_ALERTABLE) at mono-os-semaphore.h:90 [opt]
frame #2: 0x000000010bcc9411 mono`finalizer_thread at mono-coop-semaphore.h:43 [opt]
frame #3: 0x000000010bcc9405 mono`finalizer_thread(unused=<unavailable>) at gc.c:866 [opt]
frame #4: 0x000000010bc856d0 mono`start_wrapper [inlined] start_wrapper_internal at threads.c:1003 [opt]
frame #5: 0x000000010bc85633 mono`start_wrapper(data=<unavailable>) at threads.c:1063 [opt]
frame #6: 0x00007fff70b1e6c1 libsystem_pthread.dylib`_pthread_body + 340
frame #7: 0x00007fff70b1e56d libsystem_pthread.dylib`_pthread_start + 377
frame #8: 0x00007fff70b1dc5d libsystem_pthread.dylib`thread_start + 13
thread #4
frame #0: 0x00007fff70b1dc40 libsystem_pthread.dylib`start_wqthread
thread #5
frame #0: 0x00007fff709e3562 libsystem_kernel.dylib`__workq_kernreturn + 10
frame #1: 0x00007fff70b1e06a libsystem_pthread.dylib`_pthread_wqthread + 1035
frame #2: 0x00007fff70b1dc4d libsystem_pthread.dylib`start_wqthread + 13
thread #6
frame #0: 0x00007fff709e3562 libsystem_kernel.dylib`__workq_kernreturn + 10
frame #1: 0x00007fff70b1e26f libsystem_pthread.dylib`_pthread_wqthread + 1552
frame #2: 0x00007fff70b1dc4d libsystem_pthread.dylib`start_wqthread + 13
thread #7, name = 'Timer-Scheduler'
frame #0: 0x00007fff709e2cee libsystem_kernel.dylib`__psynch_cvwait + 10
frame #1: 0x00007fff70b1f69b libsystem_pthread.dylib`_pthread_cond_wait + 789
frame #2: 0x000000010bd285d4 mono`mono_os_cond_timedwait(cond=0x00007f81d382b160, mutex=0x00007f81d382b120, timeout_ms=498) at mono-os-mutex.c:44 [opt]
frame #3: 0x000000010bca6884 mono`mono_w32handle_timedwait_signal_handle [inlined] mono_w32handle_timedwait_signal_naked(cond=<unavailable>, mutex=<unavailable>, timeout=498, poll=0, alerted=<unavailable>) at w32handle.c:871 [opt]
frame #4: 0x000000010bca687c mono`mono_w32handle_timedwait_signal_handle(handle=<unavailable>, timeout=<unavailable>, poll=0, alerted=<unavailable>) at w32handle.c:988 [opt]
frame #5: 0x000000010bca66a0 mono`mono_w32handle_wait_one(handle=0x0000000000000002, timeout=498, alertable=<unavailable>) at w32handle.c:1109 [opt]
frame #6: 0x000000010bca69b6 mono`mono_w32handle_wait_multiple(handles=<unavailable>, nhandles=<unavailable>, waitall=<unavailable>, timeout=<unavailable>, alertable=<unavailable>) at w32handle.c:1145 [opt]
frame #7: 0x000000010bc80c64 mono`ves_icall_System_Threading_WaitHandle_Wait_internal(handles=<unavailable>, numhandles=<unavailable>, waitall=<unavailable>, timeout=-1, error=0x0000700007f817a8) at threads.c:1930 [opt]
frame #8: 0x0000000112ccb9dd
frame #9: 0x000000010de2edd0 mscorlib.dll.dylib`System_Threading_WaitHandle_InternalWaitOne_System_Runtime_InteropServices_SafeHandle_long_bool_bool + 64
frame #10: 0x000000010de2ed7c mscorlib.dll.dylib`System_Threading_WaitHandle_WaitOne_long_bool + 44
frame #11: 0x000000010de2ebe3 mscorlib.dll.dylib`System_Threading_WaitHandle_WaitOne_int_bool + 51
frame #12: 0x000000010de2ed0c mscorlib.dll.dylib`System_Threading_WaitHandle_WaitOne_int + 28
frame #13: 0x000000010de35cef mscorlib.dll.dylib`System_Threading_Timer_Scheduler_SchedulerThread + 2495
frame #14: 0x000000010de27b77 mscorlib.dll.dylib`System_Threading_ThreadHelper_ThreadStart_Context_object + 151
frame #15: 0x000000010de257b1 mscorlib.dll.dylib`System_Threading_ExecutionContext_Run_System_Threading_ExecutionContext_System_Threading_ContextCallback_object_bool + 33
frame #16: 0x000000010de25740 mscorlib.dll.dylib`System_Threading_ExecutionContext_Run_System_Threading_ExecutionContext_System_Threading_ContextCallback_object + 80
frame #17: 0x000000010de27cbf mscorlib.dll.dylib`System_Threading_ThreadHelper_ThreadStart + 47
frame #18: 0x000000010c52dba9
frame #19: 0x000000010baa34c7 mono`mono_jit_runtime_invoke(method=<unavailable>, obj=<unavailable>, params=0x0000700007f81ea8, exc=0x000000010c8517c8, error=<unavailable>) at mini-runtime.c:2800 [opt]
frame #20: 0x000000010bc63ed4 mono`do_runtime_invoke(method=0x00007f81d30cbcb8, obj=0x000000010c851920, params=0x0000700007f81ea8, exc=0x0000000000000000, error=0x0000700007f81e40) at object.c:2849 [opt]
frame #21: 0x000000010bc856fb mono`start_wrapper at threads.c:1011 [opt]
frame #22: 0x000000010bc85633 mono`start_wrapper(data=<unavailable>) at threads.c:1063 [opt]
frame #23: 0x00007fff70b1e6c1 libsystem_pthread.dylib`_pthread_body + 340
frame #24: 0x00007fff70b1e56d libsystem_pthread.dylib`_pthread_start + 377
frame #25: 0x00007fff70b1dc5d libsystem_pthread.dylib`thread_start + 13
(lldb) detach
=================================================================
Got a SIGSEGV while executing native code. This usually indicates
a fatal error in the mono runtime or one of the native libraries
used by your application.
=================================================================
(lldb) quit
Process 30527 detached
Abort trap: 6
Just opens a blank file and nothing happens...

Try this Nail: https://blogs.msdn.microsoft.com/jpsanders/2018/02/08/usinginstalling-fiddler-on-mac-os/

For others who may be having problems, this is what worked for me:
1. Install the cask instead of the brew:
brew cask install mono-mdk
2. Accept the xcodebuild EULA (not sure if this is necessary, but I did it so it's on here)
sudo xcodebuild -license
3. Use the --arch=32 option
mono --arch=32 Fiddler.exe
It took quite some time to come up initially, but subsequent starts are super quick.