iOS Debugger Challenge

Challenge: Bypass anti-Frida check thread names
Challenge: Understand Jailbreak detections
Challenge: Method Swizzling on non-jailbroken device
Challenge: Bypass anti-debug ptrace
Challenge: Bypass ptrace asm Syscall
Challenge: Bypass anti-debug sysctl
Challenge: Bypass anti-debug sysctl, more advanced
Challenge: Bypass anti-debug Exception Ports
Challenge: Hook Apple's Random String function
Challenge: Find Encryption key
Challenge: Dancing with Threads
Challenge: Certificate Pinning bypass with Frida
Challenge: Certificate Pinning bypass more advanced
Challenge: Adding Entitlements

Challenge: Bypass anti-Frida check ( thread names )

Running Frida on a Clean device

Since Frida version ~12.7 it is super simple to run on any iOS device. Why is it so good?

No need to repackage the iOS app.
No requirement for a Jailbroken device.

Setup Frida-Gadget

Get Frida-Gadget for iOS from https://github.com/frida/frida/releases
Copy file to new folder: cp frida-gadget.dylib ~/.cache/frida/gadget-ios.dylib

Run frida or frida-trace

With a Jailed device from the command line:

frida -U -f funky-chicken.debugger-challenge --no-pause							// frida-gadget. The --no-pause flags means the app loads as normal, after Frida is injected
frida-trace -U -f funky-chicken.debugger-challenge									// frida-trace

Get all Named Threads

How do you get all the Thread Names with iOS?

NSThread gets you the main thread and currentThread. What about threads - like Frida threads - that you did not start? An answer is defined inside of #include <mach/mach.h>. You ask the Kernel for a Thread List.

task_threads() gives you all the threads inside of app's process. After that, you call pthread_from_mach_thread_np() to converts the mach thread ID to pthreads ID. Then pthread_getname_np() to get the thread name.

Run Frida-Gadget

Now get your clean device. Make sure frida is installed on your host machine. Just connect via USB:

That got us Frida related Thread names. The detection worked.

Selecting a bypass

There are lots of ways to stop this check of Thread Names working. I liked the idea to force fail the Kernel's response, when it got a request for a Thread List. That way, I could re-use the same bypass script on other code that called into the Kernel.

In short, I would write a Frida script that is executed when the app starts. It will patch the variable named kr:

kern_return_t kr = task_threads (this_task, &thread_list, &thread_count);
if (kr != KERN_SUCCESS) {
	// handle the error.
}

There were over 50 error codes returned from the kernal. The return code was passed back as a kern_return_t type. kern_return_t was just an integer: typedef int kern_return_t;.

#include <mach/machine/kern_return.h>
	#define KERN_SUCCESS                    0
	#define KERN_INVALID_ADDRESS            1
	#define KERN_PROTECTION_FAILURE         2
	#define KERN_NO_SPACE                   3
	#define KERN_INVALID_ARGUMENT           4
	......
	....
	...

Avoiding crashes

I didn't want the bypass to disrupt other code. Let's check if task_threads is called by anybody else on my clean device:

frida-trace -i "task_threads" -U -f funky-chicken.debugger-challenge
Instrumenting functions...                                              
task_threads: Loaded handler at "/.../__handlers__/libperfcheck.dylib/task_threads.js"
Started tracing 1 function. Press Ctrl+C to stop.                       
           /* TID 0x407 */
  7387 ms  task_threads()

Ok. The calls to this api were isolated to the Frida detection only. Good news.

Double check work

I was not expecting task_threads() to be inside of libperfcheck.dylib. I was expecting it to be inside of libsystem_kernel.dylib.

Let's double-check with Frida:

frida -U -f funky-chicken.debugger-challenge --no-pause -q --eval 'var x={};Process.enumerateModulesSync().forEach(function(m){x[m.name] = Module.enumerateExportsSync(m.name)});' | | grep -B 1 -A 1 task_threads

            "address": "0x1c1c4645c",
            "name": "task_threads",
            "type": "function"

Now search for the Module, with the Exports' Address

frida -U -f funky-chicken.debugger-challenge --no-pause -q --eval 'var x={};Process.findModuleByAddress("0x1c1c4645c");'

{
    "base": "0x1c1c2a000",
    "name": "libsystem_kernel.dylib",
    "path": "/usr/lib/system/libsystem_kernel.dylib",
    "size": 200704
}

Writing a Frida Interceptor Script

Now, we can to write a script. We will invoke it with the -l flag:

frida -l task_thread.js -U -f funky-chicken.debugger-challenge --no-pause

Below is our task_threads.js script:

const module_name = "libsystem_kernel.dylib";
const exp_name = "task_threads";

function prettyExportDetail(message) {
    return '[*]' + message + '\t' + exp_name + '()\tinside: ' + module_name;
}

if (ObjC.available) {
    console.log("[*]Frida running. ObjC API available!");
    try {
        const ptrToExport = Module.findExportByName(module_name, exp_name);
        if (!ptrToExport) {
            throw new Error(prettyExportDetail('Cannot find Export:'));
        }
        console.log(prettyExportDetail('Pointer to'));

        Interceptor.attach(ptrToExport, {
            onEnter: function (args) {
                console.log(prettyExportDetail('onEnter() interceptor ->'));
                this._threadCountPointer = new NativePointer(args[2]);
                console.log('[*]Address of Thread Count:' + this._threadCountPointer );
            },

            onLeave: function (retValue) {
                this._patchInt = 4
                console.log(JSON.stringify({
                    return_value: retValue,
                    patched_return_value: this._patchInt,
                    function: exp_name,
                    thread_count: this._threadCountPointer.readPointer().toInt32()
                }));
                retValue.replace(this._patchInt)
            }
        });
    }
    catch(err){
        console.error(err.message);
    }
}
else {
    console.log("[!]Objective-C Runtime is not available!");
}

Complete

The bypass works.

Now, the code, stops checking for Frida with Named Threads because it got a kern_return_t code that it was not able to digest.

Spawned `funky-chicken.debugger-challenge`. Resuming main thread!       
[*]onEnter() interceptor ->	task_threads()	inside: libsystem_kernel.dylib
[*]Address of Thread Count:0x16f5811d4
{"return_value":"0x0","patched_return_value":4,"function":"task_threads","thread_count":15}

Challenge: Understand Jailbreak detections

Writing Jailbreak detections

Writing a self-built Jailbreak detection is tempting. But there are elegant libraries available to detect Elevated Privilege. Check out an open-source Swift version: https://github.com/securing/IOSSecuritySuite.

if IOSSecuritySuite.amIJailbroken() {
	print("This device is jailbroken")
} else {
	print("This device is not jailbroken")
}

Most of the libraries have a true/false response, at a high-level. But what happens if Apple change an API? What happens if ARM change something? What happens if a detection fails or is forced to fail? You hit two common problem in Security;false positives and a fail close / fail open policy.

A third party library can probably give you the Jailbreak == true/false plus a confidence level whether stuff failed or it was a definite jailbreak.

static func amIJailbrokenWithFailedChecks() -> (jailbroken: Bool, failedChecks: [FailedCheck]) {
    let status = performChecks()
    return (!status.passed, status.failedChecks)
}

Layers of detections are required

Not all jailbreaks are equal. You need layers of code to account for this. For example, the below code is ineffective on a device that has only has a basic jailbreak applied:

/* Loop through all loaded Dynamic libraries at run-time */
-(void)checkModules{
    unsigned int count = 0;
    NSArray *suspectLibraries = [[NSArray alloc] initWithObjects:
                                    @"SubstrateLoader.dylib",
                                    @"MobileSubstrate.dylib",
                                    @"TweakInject.dylib",
                                    @"CydiaSubstrate",
                                    @"cynject",
                                    nil];

For example, with the Electra jailbreak for iOS it could be set in two modes. Tweaks off: you can ssh to the device, start Frida manually, run a debugger. The above code is not triggered. Tweaks on will dynamically inject TweakInject.dylib at run-time, so the detection becomes useful.

Consider another example; it was common to test a write call from your app's sandbox to directory like private, root or /:

-(void)checkSandboxWrite{
	...
	..
	[stringToBeWritten writeToFile:@"/private/foobar.txt" atomically:YES encoding:NSUTF8StringEncoding error:&error];
	...
	..

This generated Code=513 "You don’t have permission to save the file “foobar.txt” in the folder “private”." {Error Domain=NSPOSIXErrorDomain Code=1 "Operation not permitted"}} on an Electra jailbroken device.

Jailbroken == YES

There are tonnes of internet articles on patching out a Boolean response to amIJailbroken(). But what happens if there no Boolean return type to find? There is likely to be a counter that increments when it finds evidence of Jailbreak. That is what this challenge offers.

Challenge: Method Swizzling on non-jailbroken device

Why Swizzle? If you understand swizzling you understand part of Objective-C's beauty. Read this from Apple :

The Objective-C language defers as many decisions as it can from compile time and link time to runtime. Whenever possible, it does things dynamically.

My goal was to method swizzle. I wanted to swap out a real random value with a value that I had chosen (42), as the below picture describes:

Step 1: Use a debugger to find information

(lldb) dclass -m YDObjCFramework
Dumping classes
************************************************************
YDHelloClass

(lldb) methods YDHelloClass
<YDHelloClass: 0x10ef63128>:
in YDHelloClass:
	Class Methods:
		+ (void) sayStaticHello; (0x10ef62ec0)
	Instance Methods:
		- (long) getRandomNumber; (0x10ef62e90)
(NSObject ...)

(lldb) exp import YDObjCFramework

(lldb) exp let $a = YDHelloClass()

(lldb) exp $a.getRandomNumber()
(Int) $R4 = 7981
(lldb) exp $a.getRandomNumber()
(Int) $R6 = 1021
(lldb) exp $a.getRandomNumber()
(Int) $R8 = 1614

Step 2: Write Swizzle code

I needed to write the code that would target the following information:

Class = YDHelloClass
Instance Method = getRandomNumber

I went back to xCode and selected New\Project\iOS\Framework\Objective-C. Using Objective-C runtime APIs, I wrote code that would target Alice's SDK.

+ (void)load
{
    Class orignalClass = objc_getClass("YDHelloClass");

    if (orignalClass != nil) {
        NSLog(@"\n[+] 🎣 Found YDHelloClass\n[+] 🎣 Placing hook on getRandomNumber\n");
        Method original, swizzled;
        original = class_getInstanceMethod(orignalClass, @selector(getRandomNumber));
        swizzled = class_getInstanceMethod(self, @selector(fakeRandomNumber));
        if(original != nil && swizzled != nil)
            method_exchangeImplementations(original, swizzled);
    }
}

@end

Step 3: Place the Swizzle

Let's start on an iOS Simulator. I used my trusty debugger connected to the app running on an XCode simulator:

lldb) process load /Users/.../swizzle_framework.framework/swizzle_framework
[+] 🎣 Found YDHelloClass

  [70b2d1d9]: https://github.com/rustymagnet3000/YDObjCFramework "YDObjCFramework"

Loading "/Users/.../swizzle_framework.framework/swizzle_framework"...ok
Image 0 loaded.

COMPLETE ( IOS SIMULATOR )

After applying the method swizzle you would always get a 42 value...

Repackage app

The way to solve this challenge on a real iOS device depended on whether you had a jailed or jailbroken device. I had a clean, jailed iOS12 device. I chose to repackage the debuggerChallenge.ipa file. This involves taking it apart, adding the dynamic framework that contained the Swizzle code and putting the app back together.

For more info on repackaging apps read here.

Approach

Build and run Debugger Challenge within xCode.
Copy the Product (which is a folder called DebuggerChallenge.app from Finder).
Copy Bob's framework to the DebuggerChallenge.app/Framework folder.
Insert a load command with Optool to the app's binary.
Put the DebuggerChallenge.app directory inside a new, empty folder named Payload.
Compress the Payload folder to unsigned.ipa.
Use Applesign to re-sign everything inside the IPA.
Use iOS-deploy to get the freshly signed app onto the Jailed device.

It all sounded simple. But I hit roadblocks:

Hiccup: OpTool

OpTool is a small repo that allows you to insert or remove Load Commands. These commands fire when your app opens and decides what dynamically linked files to load into the process.

First, you need a local copy of OpTool. You also need to ensure that you added submodules. This last step tripped me up.

git clone https://github.com/alexzielenski/optool.git
Make initialize optool’s submodules:
cd optool/
git submodule update --init --recursive

You tell the main app binary to load this new framework.

optool install -c load -p "@executable_path/Frameworks/YDBobSwizzle.framework/YDBobSwizzle" -t Payload/debugger_challenge.app/debugger_challenge

If it worked you would see..

Found FAT Header
Found thin header...
Found thin header...
Inserting a LC_LOAD_DYLIB command for architecture: arm
Successfully inserted a LC_LOAD_DYLIB command for arm
Inserting a LC_LOAD_DYLIB command for architecture: arm64
Successfully inserted a LC_LOAD_DYLIB command for arm64
Writing executable to debugger_challenge.app/debugger_challenge...

Verify it..

jtool -arch arm64 -l Payload/debugger_challenge.app/debugger_challenge

Hiccup: Code signatures

If you forgot to code sign anything, you would hit obscure Apple errors when you tried to install the app on the iPhone.

applesign -7 -i <DEVELOPER CODE SIGNING ID> -m embedded.mobileprovision unsigned.ipa -o ready.ipa
ios-deploy -b ready.ipa
ios-deploy -b debugger_challenge.app
No code signature found. AMDeviceSecureInstallApplication(0, device, url, options, install_callback, 0)

Hiccup: Entitlements

ios-deploy -b debugger_challenge.app
The executable was signed with invalid entitlements.

What had gone wrong, when I code signed the IPA? Check the file the provisioning file you passed to Applesign.

security cms -D -i embedded.mobileprovision

Expiry date, device ID were good. Had I chosen the wrong developer Code Signing ID?

<key>Entitlements</key>
<key>ExpirationDate</key>
	<date>2019-05-21T11:01:06Z</date>
<key>ProvisionedDevices</key>
	<string>0ec8227a5f623d0f4f6d257438730d79858a977f</string>
<key>TeamName</key>
	<string>Rusty Magnet</string>
<key>TeamIdentifier</key>
		<string>2N3CU4HVH8</string>

Let's try again with a new code signing ID!

security find-identity -v -p codesigning
applesign -7 -i <NEW DEVELOPER CODE SIGNING ID> -m embedded.mobileprovision debugger_chall_unsigned.ipa -o ready.ipa

That worked. I could install the app on the device.

Hiccup 4: White screen of death

Argh. The app won't open but it generated a crash log [] which you could get from XCode ].

Exception Type:  EXC_CRASH (SIGABRT)
Exception Codes: 0x0000000000000000, 0x0000000000000000
Exception Note:  EXC_CORPSE_NOTIFY
Termination Description: DYLD, Library not loaded: @executable_path/YDBobSwizzle.dylib | Referenced from: /var/containers/Bundle/Application/3F9EDE3F-7BCF-4F25-B438-9145FD3A21B7/debugger_challenge.app/debugger_challenge | Reason: image not found
Triggered by Thread:  0

I had forgotten to copy the actual framework! So I had the Load Command but no code to load!

COMPLETE ( real device )

Repeat all the above. It worked! The Swizzle was placed and working on a jailed device.

Challenge: Bypass anti-debug (ptrace)

Using ptrace on iOS is still a common technique to stop a debugger attaching to an iOS app. If you tried to attach a debugger after PT_DENY_ATTACH was issued, you would see something like this...

(lldb) process attach --pid 93791
error: attach failed: lost connection

If you attached a debugger before ptrace PT_DENY_ATTACH was set, you would see a process crash.

Use dtrace to observe the ptrace call

Unlike macOS, the header files for ptrace were not available on iOS. But You could still dynamically link to the ptrace symbol at runtime on iOS.

To see this call on an iOS Simulator, run DebuggerChallenge and hit the ptrace button, after writing this command:

sudo dtrace -qn 'syscall::ptrace:entry { printf("%s(%d, %d, %d, %d) from %s\n", probefunc, arg0, arg1, arg2, arg3, execname); }'
// ptrace(31, 0, 0, 0) from debugger_challen

This will crash your app, if XCode is attached.

Bypass steps

attach to process

process attach --pid 96441

set a regex breakpoint for ptrace

rb ptrace -s libsystem_kernel.dylib

continue after breakpoint

continue

look for the syscall

dis

print thread list

thread list

sidestep the real result

(lldb) thread return 0

COMPLETE

Challenge: Bypass ptrace (asm Syscall)

If you want to make it harder to stop ptrace being sidestepped, you could write inline assembly code. Extended inline assembly allows C language Symbols within the asm code.

Bypass steps ( manual method )

(lldb) image lookup -r -n Ptrace
****************************************************
1 hits in: debugger_challenge
****************************************************
+[YDDebuggerPtrace setPtraceWithASM]

disassemble that function:

(lldb) disas -n "+[YDDebuggerPtrace setPtraceWithASM]"
    .....
    0x104539dac <+80>:  mov    x0, #0x1a          
    0x104539db0 <+84>:  mov    x1, #0x1f
    0x104539db4 <+88>:  mov    x2, #0x0
    0x104539db8 <+92>:  mov    x3, #0x0
    0x104539dbc <+96>:  mov    x16, #0x0
    0x104539dc0 <+100>: svc    #0x1a
    .....
    ....
    ...
    ..
    .
    0x104539e0c <+176>: ret

Check value of registers:

(lldb) p/d 0x1a
(int) $5 = 26         // syscall for ptrace on arm

(lldb) p/d 0x1f
(int) $6 = 31         // PT_DENY_ATTACH == 31

Set breakpoint on the svc call: (lldb) b *0x104539dc0.

COMPLETE

When the breakpoint fires, you set the (lldb) po $x1 = 0. Depending on how the code is written, that may provide an effective bypass. That set the x1 register to the value PTRACE_TRACEME.

Challenge: Bypass anti-debug (sysctl)

The C API, Sysctl was the Apple recommended way to check if a debugger was attached to your app.

The sysctl utility retrieves kernel state and allows processes with appropriate privilege to set kernel tate.

To avoid repeating the ptrace trick, create a new, empty Swift framework that loaded a C function API named sysctl. This code would be injected into my app's process at run-time.

Create an empty Swift framework

Create an empty Swift project. Add the following C code ( from Apple ). You don't need a C header file.

Write your fake sysctl API

int sysctl(int * mib, u_int byte_size, void *info, size_t *size, void *temp, size_t(f)){

    static void *handle;
    static void *real_sysctl;
    static int fake_result = 0;

    static dispatch_once_t onceToken;
    dispatch_once(&onceToken, ^{  // ensure this is only called once & not on every function call
        handle = dlopen("/usr/lib/system/libsystem_c.dylib", RTLD_NOW);
        real_sysctl = dlsym(handle, "sysctl");  // get actual pointer
    });

    printf("Real sysctl address: %p\nFake sysctl address: %p\n", real_sysctl, sysctl);
    printf("HOOKED SYSCTL");
    return fake_result;
}

Use LLDB to load your hooking framework

(lldb) image list -b rusty_bypass
error: no modules found that match 'rusty_bypass'

Load dylib from Mac into device

Now load the process...

(lldb) process load /Users/PATH_TO_FRAMEWORK/rusty_bypass.framework/rusty_bypass
Loading "/Users/PATH_TO_FRAMEWORK/rusty_bypass.framework/rusty_bypass"...ok
Image 0 loaded.

(lldb) image lookup -s sysctl

dlopen and dlsym

Find the load address for the sysctl function inside the iOS app.

Find the load addresses for C API sysctl() in the symbol table

(lldb) expression (void*)dlopen("/usr/lib/system/libsystem_c.dylib",0x2)
(void *) $2 = 0x000000010e7086e0
(lldb) expression (void*)dlsym($2,"sysctl")
(void *) $3 = 0x0000000113be7c04

Ok, now check my address of my bypass...

(lldb) expression (void*)dlopen("/Users/..../rusty_bypass.framework/rusty_bypass",0x2)
(lldb) ) $4 = 0x0000604000133ec0
(lldb) expression (void*)dlsym($4,"sysctl")
(void *) $5 = 0x000000012e292dc0

Challenge - failed first attempt

Now the rusty_bypass framework was loaded, I half expected it to work. No. the libsystem_kernel sysctl was called before my own code.

Symbol table to the rescue

(lldb) image dump symtab -m libsystem_c.dylib
Now check your Load Address:  0x0000000113be7c04  for `sysctl`

Verify what you found, the easy way

(lldb) image lookup -a $rip
      Address: libsystem_c.dylib[0x0000000113be7c04]
      (libsystem_c.dylib.__TEXT.__text + 170512)
      Summary: libsystem_c.dylib`sysctl

Set a breakpoint

(lldb) b 0x0000000113be7c04           
(lldb) register read

Whoop whoop

This was the killer step. The fruits of labor...

General Purpose Registers:
       rax = 0x000000000000028e
        .....
        .....
        .....
       rip = 0x0000000113be7c04  libsystem_c.dylib sysctl

Change load address of API call

(lldb) register write rip 0x000000012e292dc0
rip = 0x000000012e292dc0  rusty_bypass`sysctl at hook_debugger_check.c:5
(lldb) continue

COMPLETE

This was a cumbersome way to overwrite a register. There is a much simpler and reliable way to patch out anto-debug registers at run-time.

Challenge: Bypass anti-debug ( sysctl, more advanced )

sysctl asks the Kernel to detect if a process is being debugged. The result is the P_TRACED flag gets set. This is defined inside of /sys/proc.h. How does sysctl tell the Kernel which process ID it wants to check ? Let's inspect.

(lldb) b sysctl
Breakpoint 3: where = libsystem_c.dylib`sysctl, address = 0x00007fff5214c304

At this point, you can read what is inside the registers.

sysctl(mib, sizeof(mib) / sizeof(*mib), &info, &size, NULL, 0);

You could read memory to understand what was passed into each register. Is there a better simpler way ? You can use the call stack and move to frame before sysctl:

(lldb) bt
(lldb) frame select 1

Now you can observe the real variable settings:

(lldb) frame variable -A
(lldb) p mib
(int [4]) $14 = ([0] = 1, [1] = 14, [2] = 1, [3] = 23490)

Now - with the Apple documentation - we can see that the interesting value in mib[3] is the app's process ID.

  mib[0] = CTL_KERN;
  mib[1] = KERN_PROC;
  mib[2] = KERN_PROC_PID;		/* by process id */
  mib[3] = getpid();		/* current process ID */

If you did want to read memory instead of using the call stack, you could:

(lldb) po (int *) mib
0x00007ffee5f99610

(lldb) mem read 0x00007ffee646e610  -f d -c 4
0x7ffee5f99610: 1
0x7ffee5f99614: 14
0x7ffee5f99618: 1
0x7ffee5f9961c: 23490

COMPLETE

Now we can bypass the check by patching out the value inside of mib[3]:

(lldb) p/x 0x00007ffee646e610 + 12      // mib[3]
(long) $16 = 0x00007ffee646e61c

(lldb) po getppid()
23493

(lldb) po mib[3]=23493
23493   // overwrite the getpid() with getppid()

Challenge: Bypass anti-debug (Exception Ports)

Another anti-debug technique on macOS / iOS was to check if a debugger was attached by looking if any of the Ports used by a Debugger returned a valid response.

This relied on the C task_get_exception_ports API. You passed in the Exception Port you wanted to check. This was always argument 2 ( arg2) to the function.

This was less well known tha ptrace or sysctl. The following references were great:

https://alexomara.com/blog/defeating-anti-debug-techniques-macos-mach-exception-ports/

http://web.mit.edu/darwin/src/modules/xnu/osfmk/man/task_get_exception_ports.html

https://zgcoder.net/ramblings/osx-debugger-detection.html

https://github.com/apple/darwin-xnu/blob/master/osfmk/mach/exception_types.h

Bypass steps

set breakpoint

(lldb) b task_get_exception_ports
Breakpoint 3: where = libsystem_kernel.dylib`task_get_exception_ports, address = 0x00007fff6a530675

continue

(lldb) c

print values found by exception ports

(lldb) p $arg2

write new value

(lldb) reg w rsi 0

continue

(lldb) c

COMPLETE

No debugger detected.

Challenge: Hook Apple's Random String function

I started with some simple Swift code. Could I whiten the UUID to a value I predefined?

@IBAction func random_string_btn(_ sender: Any) {
    let randomString = NSUUID().uuidString
    present_alert_controller(user_message: "Random string: \(randomString)")
}

Use debugger to find the API

(lldb) image lookup -rn uuidString
<nothing returned >

(lldb) lookup NSUUID -m Foundation
****************************************************
14 hits in: Foundation
****************************************************
-[NSUUID init]
-[NSUUID hash]
+[NSUUID UUID]

Although the API was called via Swift, it was an Objective-C Class.I attached frida to learn more.

[iPhone::Debug CrackMe]-> ObjC.classes.NSUUID.UUID().toString();
"6C402B55-6AFC-494A-B976-BCA781801A0A"

You could invoke the class with lldb:

(lldb) po [NSUUID UUID]
<__NSConcreteUUID 0x6000006374a0> 6BC8E049-2EFD-4BAA-B2AB-456E69AC74F8

(lldb) po [NSUUID UUID]
<__NSConcreteUUID 0x60400043fbc0> A41E59A5-C7C6-470F-88ED-48130BD85D1F

This was interesting. Every time you called that static method it would add the pointer to the heap. They were not deallocated. Perhaps this was a way to ensure a repeated GUID was never given?

A disassemble revealed some interesting elements.

(lldb) disassemble -n "+[NSUUID UUID]" -c10

If you move to the init call - in the asm code, the 32-byte field was set to zeros.

(lldb) po (char*) $rax
<__NSConcreteUUID 0x6040006234a0> 00000000-0000-0000-0000-000000000000

Failed on first attempt....

It appeared you could not trust the return register. As it did not match what Swift presented to the user.

failed on 2nd, 3rd, 4th, n attempts

frida-trace -m "*[NSUUID **]" -U -f funky-chicken.debugger-challenge

Instrumenting 27 functions.

The 4 I cared about were as follows:

+[NSUUID UUID]:
-[NSUUID init]:
-[NSUUID UUIDString]:
-[__NSConcreteUUID UUIDString]:

Frida-Trace generated a javascript file template when the above command ran. I changed the javascript code to:

  onLeave: function (log, retval, state) {
     var message = ObjC.Object(retval);
     log("[+][__NSConcreteUUID UUIDString] -->\n\"" + message.toString() + "\"");
  }

FAILED

Something was odd about this API. It generated multiple UUID's every time you called the API. But with Frida or lldb I could never find the actual return value going back to the swift code which was simply:

let randomString = UUID()
print(randomString.uuidString)

Challenge: Find Encryption key

I added a popular RNCryptor wrapper around Apple's CommonCrypto library. I statically embedded this into the Debugger Challenge instead of adding as a CocoaPod.

The CommonCrypto API CCCryptorCreate init was the target. It was invoked behind this Swift code that called into the RNCryptor.encrypt API:

    // Encrypt
    let myString = "Ewoks don't wear pyjamas."
    let myData = myString.data(using: String.Encoding.utf8)! as Data  // note, not using NSData
    let password = "AAAAAAAA" // eight 0x41 values in hex
    let ciphertext = RNCryptor.encrypt(data: myData, withPassword: password)

Leverage Frida-Trace

frida-trace -i "CCCryptorCreate*" -U "Debug CrackMe"

Out of the box, this tells you interesting information.

Trace	RNCryptor Definition
op=0x0	Encrypt
alg=0x0	kCCAlgorithmAES128
options=0x1	kCCOptionPKCS7Padding
keyLength=0x20	kCCKeySizeAES256 = 32 (0x20 in hex)
key	A pointer to the Binary key (Data encoded)
iv	A pointer to the Binary I.V. (Data encoded)
cryptorRef	Opaque reference to a CCCryptor object

Watch the encryption key with a Frida-Script

/* Usage:   frida -U "Debug CrackMe" -l cc_hook.js --no-pause */

console.log("[+] script started...")
if (ObjC.available)
{
  if (Process.isDebuggerAttached() == true)
  {
    console.log("[+] Debugger attached, in addition to Frida.");
  }
  var a = Process.arch.toString()
  console.log("[+] Device chip: " + a);

  var f = Module.findExportByName("libcommonCrypto.dylib","CCCryptorCreate");

  if (f){
      console.log("[+] Found common crypto: " + f);
      Interceptor.attach(f, {
          onEnter: function (args) {
              console.log("inside init statement for CCCryptorCreate. Key, IV and algorithm available");
          }
      });
  }
}
else
{
    console.log("[+] Objective-C Runtime not available!");
}
console.log("[+] ...script completed")

Where is the plaintext about to be encrypted?

If you look at http://www.manpagez.com/man/3/CCCryptorCreate/ this API will lead to the Encryption Key. But what if I want the actual plaintext that is being encrypted? You can use lldb to show the lifecycle of the CommonCrypto API calls. The flow is the same for encrypt and decrypt.

(lldb) rb CCCrypt

The man page tells you the plaintext is sent into this API:

CCCryptorUpdate(CCCryptorRef cryptorRef, const void *dataIn,
         size_t dataInLength, void *dataOut, size_t dataOutAvailable,
         size_t *dataOutMoved);

Now we have our target - argument 2 - let's use lldb to reveal the plaintext.

RDI - first arg, RSI - second arg, RCX - fourth arg

lldb) rb CCCryptorUpdate
Breakpoint 1: where = libcommonCrypto.dylib`CCCryptorUpdate, address = 0x000000010b91092c
(lldb) c
Process 11315 resuming

(lldb) register read
General Purpose Registers:
       rsi = 0x000060400044a2a0

Note ->  RSI can be access via $arg2 in lldb
(lldb) po (char*) $arg2
"Ewoks don't wear pyjamas."

(lldb) memory read 0x000060400044a2a0
0x60400044a2a0: 45 77 6f 6b 73 20 64 6f 6e 27 74 20 77 65 61 72  Ewoks don't wear
0x60400044a2b0: 20 70 79 6a 61 6d 61 73 2e 00 00 00 00 00 00 00   pyjamas........

What is the decrypted plaintext?

(lldb) b CCCryptorFinal
(lldb) c
(lldb) po (char*) $arg2
(lldb) po (char*) $rsi
(lldb) mem read 0x00006040000106a0 -c10

Sometimes, the decrypted text was not together. I had an assumption this related to the C Malloc API - that was used the hood by CommonCrypto. Malloc was not always given sequential blocks of memory from the O/S.

Failed to get raw key

(lldb) rb CCCryptorCreateWithMode
Breakpoint 1: where = libcommonCrypto.dylib`CCCryptorCreateWithMode, address = 0x00000001826c8474
(lldb) rb CCCryptorCreateWithMode

API definition from Apple:
CCCryptorCreateWithMode(op, mode, alg, padding, iv, key, keyLength, tweak, tweakLength, numRounds, modeOptions, cryptorRef);

To get the Key Length.....
(lldb) po (size_t) $arg7
32  // 256 bit key

To get the raw key...
(lldb) memory read -s4 -fx -c32 $arg6
<< never get an understandble key, in here. >>

COMPLETE

Using the CCCryptorCreate API spec, we can see which arguments to read.

CCCryptorCreate(CCOperation op, CCAlgorithm alg, CCOptions options,
         const void *key, size_t keyLength, const void *iv,
         CCCryptorRef *cryptorRef);

With a pre-defined key 16 byte key (128 bits), I can read it with the following debugger commands.

(lldb) b CCCryptorCreate
Breakpoint 1: where = libcommonCrypto.dylib`CCCryptorCreate, address = 0x000000010a6d51b7

(lldb) reg read $arg4
     rcx = 0x000060800003a590

(lldb) mem read 0x000060800003a590
0x60800003a590: 41 41 41 41 41 41 41 41 41 41 41 41 41 41 41 41  AAAAAAAAAAAAAAAA

(lldb) memory read -s16 -fC $arg4
0x60800003a590: AAAAAAAAAAAAAAAA

(lldb) memory read -s16 -fx -c1 $arg4
0x60800003a590: 0x41414141414141414141414141414141

If you read the Initialization vector, lldb cannot display a lot of the characters. That is because the code callinto into the API SecRandomCopyBytes which gives a lot of extended / non-Ascii characters. You can still read it by forcing it to print in hex.

(lldb) mem read -s1 -fx $arg6
0x6080002668c0: 0x46 0xbc 0x72 0xc9 0x04 0xfb 0xb5 0xd6

Useful references

https://richardwarrender.com/2016/04/encrypt-data-using-aes-and-256-bit-keys/

https://stackoverflow.com/questions/25754147/issue-using-cccrypt-commoncrypt-in-swift

Challenge: Dancing with Threads

The idea of this challenge was to manipulate an iOS that used multiple background Threads to achieve a task. For this, I wanted to re-order the Cars and Airplanes.

Attempt 1 - NSThread sleepForTimeInterval

As there were two background threads - each adding to a single array - I had to set a good breakpoint on a specific thread:

 (lldb) exp NSTimeInterval $blockThreadTimer = 0.5;
 (lldb) exp [NSThread sleepForTimeInterval:$blockThreadTimer];

Something was wrong, with my first attempt. What happened to the Airplanes? Well, it was a bug in the code. The line of code that blocked the main thread from returning from the Thread Chomper code only waited for a single background thread. After adding:

dispatch_semaphore_wait(semaphore, DISPATCH_TIME_FOREVER);

Bypass steps

Breakpoints are better when set on a specific Thread. Type the following into your debugger:

breakpoint set after one of the dispatch_async calls
breakpoint set  --file thread_chomper.m --line 34 thread 5
(lldb) expression
NSTimeInterval $blockThreadTimer = 2;
[NSThread sleepForTimeInterval:$blockThreadTimer];
// ENTER to finish expression

COMPLETE

I was not satisfied with attempt 1. It was only available on debug builds, where you could set simple breakpoints. Better would be to alter the parameters passed into Apple's Grand Central Dispatch Quality of Service. This was called was asking - in code - " I want a background thread, please ".

dispatch_async(dispatch_get_global_queue(DISPATCH_QUEUE_PRIORITY_DEFAULT, 0), ^{

Challenge: Certificate Pinning bypass ( with Frida )

Do I trust this server, before establishing a connection to this server?

That question is what Certificate Pinning adds to a mobile app. It derives the answer by comparing Public Keys it has stored locally against Public Keys sent by the Server during a secured network setup.

Hardened iOS app's often ignore the default iOS Truststore and add their own, smaller list of Root and Intermediary Certificate Authorities. This smaller list was called a pinlist.

Why ignore the iOS Truststore? It contained a lot of Certificate Authorities. Refer to https://en.wikipedia.org/wiki/DigiNotar if you want details of why this is a bad thing. More relevant for this Challenge, a user could add an all powerful Self-Signed Certificate via the Settings app on iOS. This would be "trusted" by iOS.

This challenge was written to show how to get around checks performed when sending a network request with Apple's NSURLSession class.

If you send traffic with NSURLSession and it was https [ the default since iOS 9 ] the NSURLSessionDelegate would invoke the following method:

func urlSession(_ session: URLSession, didReceive challenge: URLAuthenticationChallenge, completionHandler: @escaping (URLSession.AuthChallengeDisposition, URLCredential?) -> Void) {

This was a great place for a developer to add Cert Pinning checks. If an app is Pinning against the iOS Truststore you would see code like this:

guard let trust: SecTrust = challenge.protectionSpace.serverTrust else {
    return
}
var secResult = SecTrustResultType.invalid
var osStatus = SecTrustEvaluate(trust, &secResult)

If the app code could not verify the Certificate Chain the secResult would be set to negative value. Afterwards, the app would probably call completionHandler(.cancelAuthenticationChallenge, nil) to cancel the attempted TLS connection.

Attempt 1 - Bypass iOS Truststore

Using Frida I used a script that would write over the secResult variable. This was written to with this call SecTrustEvaluate(trust, &secResult). I would effectively be changing a DENY to a PROCEED.

const moduleName = 'Security';
const functionName = 'SecTrustEvaluate';
const SecTrustEvaluatePtr = Module.findExportByName(moduleName, functionName);

try {
    if (SecTrustEvaluatePtr == null) {
        throw '[*] %s not found', moduleName, functionName;
    }
    console.log('[*] Script loaded. ' + moduleName + '.' + functionName + '\tpointer: '+ SecTrustEvaluatePtr);

    Interceptor.replace(SecTrustEvaluatePtr,new NativeCallback(function(trust,result) {

        console.log('[*]SecTrustEvaluate called');
        console.log('\tDefault SecTrustResultType: ', Memory.readU32(result));
        Memory.writeU32(result,1);
        console.log('\tnew SecTrustResultType: ', Memory.readU32(result));
        return 0;   // Return errSecSuccess to OSStatus call
    } ,'int',['pointer','pointer']));
}
catch(err){
    console.log('[!] Exception: ' + err.message);
}

COMPLETE

[*]SecTrustEvaluate called
	Default SecTrustResultType:  3
	new SecTrustResultType:  1
[*]SecTrustEvaluate called
	Default SecTrustResultType:  0
	new SecTrustResultType:  1

Challenge: Certificate Pinning bypass ( more advanced )

The Frida bypass worked well for trivial iOS Truststore pinning. But what happened if the app checked a locally held list of Public Keys ( the pinlist ) against the Public Keys it received during the client-server TLS setup Z?

I could use Frida trace to get me so far. I could also statically patch out the code. But the latter is hard and takes a lot of analysis. How about I Method Swizzle to avoid this line of code?

completionHandler(.cancelAuthenticationChallenge, nil)

I wrote the following Method Swizzle to ignore all checks and proceed with the TLS setup?

- (void)YDHappyChallenge:(NSURLSession *)session didReceiveChallenge:(NSURLAuthenticationChallenge *)challenge completionHandler:(void (^)(NSURLSessionAuthChallengeDisposition, NSURLCredential *))completionHandler{

    NSLog(@"🍭NSURLSession on: %@", [[challenge protectionSpace] host]);
    completionHandler(NSURLSessionAuthChallengePerformDefaultHandling, NULL);
}

COMPLETE

The swizzle was a lot more effective. The only trick was to ensure that the Swizzle inherited from NSObject instead of NSURLSession.

Not all Cert Pinning checks were bypassed using these methods.

Challenge: Adding Entitlements

Let's try and add a basic entitlement, after the app is in the wild. Normally you have to add entitlement by creating a new provisioning profile at: https://developer.apple.com/.

There was a long list of available entitlements:

https://developer.apple.com/documentation/bundleresources/entitlements

Open XCode and select /File/New/PropertyList. Now add com.apple.developer.contacts.notes as a Boolean set to 1.

If you want to read the file from the command line:

plistutil -i entitlements.plist -f xml:

<?xml version="1.0" encoding="UTF-8"?>
<!DOCTYPE plist PUBLIC "-//Apple//DTD PLIST 1.0//EN" "http://www.apple.com/DTDs/PropertyList-1.0.dtd">
<plist version="1.0">
<dict>
	<key>com.apple.developer.contacts.notes</key>
	<true/>
</dict>
</plist>

Now let's get ready to code sign an already generated ipa file:

get code signing ID

security find-identity -v -p codesigning

Find the "Apple Development" ID, if the developer license is paid

create variable for key

export CODESIGNID=xxxx

code sign

Now we need to code sign EVERYTHING that is inside of the app bundle. There are a few articles online about code signing that only sign the binary. But all the dynamic frameworks, bundles, assets also get signed.

I used applesign which was a NodeJS module and command line utility for re-signing iOS applications.

applesign -7 -i ${CODESIGNID} -m embedded.mobileprovision -e entitlements.plist extracted.ipa

install app

ios-deploy -W -b signed.ipa

Error - invalid entitlements

The first error is:Error 0xe8008016: The executable was signed with invalid entitlements.

Create new Bundle ID

applesign -7 -i ${CODESIGNID} -m embedded.mobileprovision -e entitlements.plist extracted.ipa -b com.fresh.id

The same error.

TBC.

Name		Name	Last commit message	Last commit date
Latest commit History 122 Commits
.github/workflows		.github/workflows
Frameworks		Frameworks
RNCryptor		RNCryptor
debugger_challenge.xcodeproj		debugger_challenge.xcodeproj
debugger_challenge		debugger_challenge
images/2021/01		images/2021/01
README.md		README.md
entitlements.plist		entitlements.plist

rustymagnet3000/ios_debugger_challenge

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iOS Debugger Challenge

Challenge: Bypass anti-Frida check ( thread names )

Running Frida on a Clean device

Setup Frida-Gadget

Run frida or frida-trace

Get all Named Threads

Run Frida-Gadget

Selecting a bypass

Avoiding crashes

Double check work

Writing a Frida Interceptor Script

Complete

Challenge: Understand Jailbreak detections

Writing Jailbreak detections

Layers of detections are required

Jailbroken == YES

Challenge: Method Swizzling on non-jailbroken device

Step 1: Use a debugger to find information

Step 2: Write Swizzle code

Step 3: Place the Swizzle

COMPLETE ( IOS SIMULATOR )

Repackage app

Approach

Hiccup: OpTool

Hiccup: Code signatures

Hiccup: Entitlements

Hiccup 4: White screen of death

COMPLETE ( real device )

Challenge: Bypass anti-debug (ptrace)

Use dtrace to observe the ptrace call

Bypass steps

attach to process

set a regex breakpoint for ptrace

continue after breakpoint

look for the syscall

print thread list

sidestep the real result

COMPLETE

Challenge: Bypass ptrace (asm Syscall)

Bypass steps ( manual method )

COMPLETE

Challenge: Bypass anti-debug (sysctl)

Create an empty Swift framework

Write your fake sysctl API

Use LLDB to load your hooking framework

Load dylib from Mac into device

dlopen and dlsym

Find the load addresses for C API sysctl() in the symbol table

Challenge - failed first attempt

Symbol table to the rescue

Verify what you found, the easy way

Set a breakpoint

Whoop whoop

Change load address of API call

COMPLETE

Challenge: Bypass anti-debug ( sysctl, more advanced )

COMPLETE

Challenge: Bypass anti-debug (Exception Ports)

Bypass steps

set breakpoint

continue

print values found by exception ports

write new value

continue

COMPLETE

Challenge: Hook Apple's Random String function

Use debugger to find the API

Failed on first attempt....

failed on 2nd, 3rd, 4th, n attempts

FAILED

Challenge: Find Encryption key

Leverage Frida-Trace

Watch the encryption key with a Frida-Script

Where is the plaintext about to be encrypted?

What is the decrypted plaintext?