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Before yesterdaysecret club

Abusing MacOS Entitlements for code execution

14 August 2020 at 23:00

Recently I disclosed some vulnerabilities to Dropbox and PortSwigger via H1 and Microsoft via MSRC pertaining to Application entitlements on MacOS. We’ll be exploring what entitlements are, what exactly you can do with them, and how they can be used to bypass security products.

These are all unpatched as of publish.

What’s an Entitlement?

On MacOS, an entitlement is a string that grants an Application specific permissions to perform specific tasks that may have an impact on the integrity of the system or user privacy. Entitlements can be viewed with the comand codesign -d --entitlements - $file.

Viewing the entitlements of the main Dropbox binary.

For the above image, we can see the key entitlements com.apple.security.cs.allow-unsigned-executable-memory and com.apple.security.cs.disable-library-validation - they allow exactly what they say on the tin. We’ll explore Dropbox first, as it’s the more involved of the two to exploit.


Just as Windows has PE and Linux has ELF, MacOS has its own executable format, Mach-O (short for Mach-Object). Mach-O files are used on all Apple products, ranging from iOS, to tvOS, to MacOS. In fact, all these operating systems share a common heritage stemming from NeXTStep, though that’s beyond the scope of this article.

MacOS has a variety of security protections in place, including Gatekeeper, AMFI (AppleMobileFileIntegrity), SIP (System Integrity Protection, a form of mandatory access control), code signing, etc. Gatekeeper is akin to Windows SmartScreen in that it fingerprints files, checks them against a list on Apple’s servers, and returns the value to determine if the file is safe to run. `

This is vastly simplified.

There are three configurable options, though the third is hidden by default - App Store only, App Store and identified developers, and “anywhere”, the third presumably hidden to minimize accidental compromise. Gatekeeper can also be managed by the command line tool, spctl(8), for more granular control of the system. One can even disable Gatekeeper entirely through spctl --master-disable, though this requires superuser access. It’s to be noted that this does not invalidate rules already in the System Policy database (/var/db/SystemPolicy), but allows anything not in the database, regardless of notarization, etc, to run unimpeded.

Now, back to Dropbox. Dropbox is compiled using the hardened runtime, meaning that without specific entitlements, JIT code cannot be executed, DYLD environment variables are automatically ignored, and unsigned libraries are not loaded (often resulting in a SIGKILL of the binary.) We can see that Dropbox allows unsigned executable memory, allowing shellcode injection, and has library validation disabled - meaning that any library can be inserted into the process. But how?

Using LIEF, we can easily add a new LoadCommand to Dropbox. In the following picture, you can see my tool, Coronzon, which is based off of yololib, doing the same.

Adding a LoadCommand to Dropbox

import lief

file = lief.parse('Dropbox')

Using code similar to the following, one can execute code within the context of the Dropbox process (albeit via voiding the code signature - you’re best off stripping the code signature, or it won’t run from /Applications/). You’ll either have to strip the code signature or ad-hoc sign it to get it to run from /Applications/, though the application will lose any entitlements and TCC rights previously granted. You’ll have to use a technique known as dylib proxying - which is to say, replacing a library that is part of the application bundle with one of the same name that re-exports the library it’s replacing. (Using the link-time flags `-Xlinker -reexport_library $(PATH_TO_LIBRARY)).

#include <stdio.h>
#include <stdlib.h>
#include <syslog.h>

static void customConstructor(int argc, const char **argv)
     printf("Hello from dylib!\n");
     syslog(LOG_ERR, "Dylib injection successful in %s\n", argv[0]);
     system("open -a Calculator");

This is a simple example, but combined with something like frida-gum the impact becomes much more severe - allowing application introspection and runtime modification without the user’s knowledge. This makes for a great, persistent usermode implant, as Dropbox is added as a LaunchItem.

Visual Studio

Microsoft releases a cut-down version of their premier IDE for MacOS, mainly for C# development with Xamarin, .NET Core, and Mono. Though ‘cut-down’, it still supports many features of the original, including NuGet, IntelliSense, and more.

It also has some interesting entitlements.

Viewing the entitlements of the main Visual Studio binary.

Of course, MacOS users are treated as second class citizens in Microsoft’s ecosystem and Microsoft could not give a damn about the impact this has on the end user - which is similar in impact to the above, albeit more severe. We can see that basically every single feature of the hardened runtime is disabled - enabling the simplest of code injection methods, via the DYLD_INSERT_LIBRARIES environment variable. The following video is a proof of concept of just how easily code can be executed within the context of Visual Studio.

Keep in mind: code executing in this context will inherit the entitlements and TCC values of the parent. It’s not hard to imagine a scenario in which IP (intellectual property) theft could result from Microsoft’s attempts at ‘hardening’ Visual Studio for Mac. As with Dropbox, all the security implications are the same, yet it’s about 30x easier to pull off as DYLD environment variables are allowed.

Burp Suite

I’m sure most reading this article are familiar with Burp Suite. If not - it’s a web exploitation Swiss army knife that aids in recon, pre, and post-exploitation. So why don’t we exploit it?

This time, we’ll be exploiting the Burp Suite installer. As you’ll probably guess by now, it has some… interesting entitlements.

Viewing the entitlements of the Burp Installer stub.

Aside from the output lacking newlines, exploitation in this case is different. There are no shell scripts in the install (nor is the entitlement for allowing DYLD environment variables present), and if we’re going to create a malicious installer, we need to use what’s already packaged. So, we’ll tamper with the included JRE (jre.tar.gz) that’s included with the installer.

There’s actually two approaches to this - replacing a dylib outright or dylib hijacking. Dylib hijacking is similar to it’s partner, DLL hijacking, on Windows, in that it abuses the executable searching for a library that may or may not be there, usually specified by @rpath or sometimes a ‘weakref’. A weakref is a library that doesn’t need to be loaded, but can be loaded. For more information on dylib hijacking, I reccomend this excellent presentation by Patrick Wardle of Objective-See. For brevity, however, we’ll just be replacing a .dylib in the JRE.

The way the installer executes is that it extracts the JRE to a temporary location during install, which is used for the rest of the install. This temporary location is randomized and actually adds a layer of obfuscation to our attack, as no two executions will have the JRE extracted into the same place. Once the JRE is extraced, it’s loaded and attempts to install Burp Suite. This allows us to execute unsigned code under the guise and context of Burp Suite, running code in the background unbenknownst to the user. Thankfully Burp Suite doesn’t (currently) require elevated privileges to install on macOS. Nonetheless, this is an issue due to the ease of forging a malicious installer and the fact that Gatekeeper is none the wiser.

A proof of concept can be viewed below.


Entitlements are both a valuable component of MacOS’ security model, but can also be a double edged sword. You’ve seen how trivivally Gatekeeper and existing OS protections can be bypassed by leveraging a weak application as a trampoline - the one with the most impact in this case I argue to be Dropbox, due to inheritance of Dropbox’s TCC permissions and being a LaunchItem, thus gaining persistence. Thus, entitlements provide a valuable addition to the attack surface of MacOS for any red-teamer or bug-bounty hunter. Your mileage may vary, however - Dropbox and Microsoft didn’t seem to care much. (PortSwigger, on the other hand, admitted that due to the design of Burp Suite and inherent language intrinsics it’s extremely hard to prevent such an attack - and I don’t fault them).

Happy hacking.

Disclosure Timelines


  • June 11th, initial disclosure.
  • June 17th, additional information added
  • June 20th, closed as Informative

Visual Studio

  • June 19th, initial disclosure
  • June 22nd, closed (“Upon investigation, we have determined that this submission does not meet the bar for security servicing. This report does not appear to identify a weakness in a Microsoft product or service that would enable an attacker to compromise the integrity, availability, or confidentiality of a Microsoft offering. “)

Burp Suite

  • June 27th, initial disclosure
  • June 30th, closed as Informative

Source Engine Memory Corruption via LUMP_PAKFILE

5 May 2020 at 23:00

A month or so ago I dropped a Source engine zero-day on Twitter without much explanation of what it does. After determining that it’s unfortunately not exploitable, we’ll be exploring it, and the mess that is Valve’s Source Engine.


Valve’s Source Engine was released initially on June 2004, with the first game utilizing the engine being Counter-Strike: Source, which was released itself on November 1, 2004 - 15 or so years ago. Despite being touted as a “complete rewrite” Source still inherits code from GoldSrc and it’s parent, the Quake Engine. Alongside the possibility of grandfathering in bugs from GoldSrc and Quake (GoldSrc itself a victim of this), Valve’s security model for the engine is… non-existent. Valve not yet being the powerhouse they are today, but we’re left with numerous stupid fucking mistakes, dude, including designing your own memory allocator (or rather, making a wrapper around malloc.).

Of note - it’s relatively common for games to develop their own allocator, but from a security perspective it’s still not the greatest.

The Bug

The byte at offset A47B98 in the .bsp file I released and the following three bytes (\x90\x90\x90\x90), parsed as UInt32, controls how much memory is allocated as the .bsp is being loaded, namely in CS:GO (though also affecting CS:S, TF2, and L4D2). That’s the short of it.

To understand more, we’re going to have to delve deeper. Recently the source code for CS:GO circa 2017’s Operation Hydra was released - this will be our main tool.

Let’s start with WinDBG. csgo.exe loaded with the arguments -safe -novid -nosound +map exploit.bsp, we hit our first chance exception at “Host_NewGame”.

---- Host_NewGame ----
(311c.4ab0): Break instruction exception - code 80000003 (first chance)
*** WARNING: Unable to verify checksum for C:\Users\triaz\Desktop\game\bin\tier0.dll
eax=00000001 ebx=00000000 ecx=7b324750 edx=00000000 esi=90909090 edi=7b324750
eip=7b2dd35c esp=012fcd68 ebp=012fce6c iopl=0         nv up ei pl nz na po nc
cs=0023  ss=002b  ds=002b  es=002b  fs=0053  gs=002b             efl=00000202
7b2dd35c cc              int     3

On the register $esi we can see the four responsible bytes, and if we peek at the stack pointer –

Full stack trace removed for succinctness.

00 012fce6c 7b2dac51 90909090 90909090 012fd0c0 tier0!CStdMemAlloc::SetCRTAllocFailed+0x1c [cstrike15_src\tier0\memstd.cpp @ 2880] 
01 (Inline) -------- -------- -------- -------- tier0!CStdMemAlloc::InternalAlloc+0x12c [cstrike15_src\tier0\memstd.cpp @ 2043] 
02 012fce84 77643546 00000000 00000000 00000000 tier0!CStdMemAlloc::Alloc+0x131 [cstrike15_src\tier0\memstd.cpp @ 2237] 
03 (Inline) -------- -------- -------- -------- filesystem_stdio!IMemAlloc::IndirectAlloc+0x8 [cstrike15_src\public\tier0\memalloc.h @ 135] 
04 (Inline) -------- -------- -------- -------- filesystem_stdio!MemAlloc_Alloc+0xd [cstrike15_src\public\tier0\memalloc.h @ 258] 
05 (Inline) -------- -------- -------- -------- filesystem_stdio!CUtlMemory<unsigned char,int>::Init+0x44 [cstrike15_src\public\tier1\utlmemory.h @ 502] 
06 012fce98 7762c6ee 00000000 90909090 00000000 filesystem_stdio!CUtlBuffer::CUtlBuffer+0x66 [cstrike15_src\tier1\utlbuffer.cpp @ 201]

Or, in a more succinct form -

0:000> dds esp
012fcd68  90909090

The bytes of $esi are directly on the stack pointer (duh). A wonderful start. Keep in mind that module - filesystem_stdio — it’ll be important later. If we continue debugging —

***** OUT OF MEMORY! attempted allocation size: 2425393296 ****
(311c.4ab0): Access violation - code c0000005 (first chance)
First chance exceptions are reported before any exception handling.
This exception may be expected and handled.
eax=00000032 ebx=03128f00 ecx=012fd0c0 edx=00000001 esi=012fd0c0 edi=00000000
eip=00000032 esp=012fce7c ebp=012fce88 iopl=0         nv up ei ng nz ac po nc
cs=0023  ss=002b  ds=002b  es=002b  fs=0053  gs=002b             efl=00010292
00000032 ??              ???

And there we see it - the memory allocator has tried to allocate 0x90909090, as UInt32. Now while I simply used HxD to validate this, the following Python 2.7 one-liner should also function.

print int('0x90909090', 0)

(For Python 3, you’ll have to encapsulate everything from int onward in that line in another set of parentheses. RTFM.)

Which will return 2425393296, the value Source’s spaghetti code tried to allocate. (It seems, internally, Python’s int handles integers much the same way as ctypes.c_uint32 - for simplicity’s sake, we used int, but you can easily import ctypes and replicate the finding. Might want to do it with 2.7, as 3 handles some things oddly with characters, bytes, etc.)

So let’s delve a bit deeper, shall we? We would be using macOS for the next part, love it or hate it, as everyone who writes cross-platform code for the platform (and Darwin in general) seems to forget that stripping binaries is a thing - we don’t have symbols for NT, so macOS should be a viable substitute - but hey, we have the damn source code, so we can do this on Windows.


One important thing to do before we go fully into exploitation is minimize the bug. The bug is a derivative of one found with a wrapper around zzuf, that was re-found with CERT’s BFF tool. If we look at the differences between our original map (cs_assault) and ours, we can see the differences are numerous.

Diff between files

Minimization was done manually in this case, using BSPInfo and extracting and comparing the lumps. As expected, the key error was in lump 40 - LUMP_PAKFILE. This lump is essentially a large .zip file. We can use 010 Editor’s ZIP file template to examine it.

Symbols and Source (Code)

The behavior between the Steam release and the leaked source will differ significantly.

No bug will function in a completely identical way across platforms. Assuming your goal is to weaponize this, or even get the maximum payout from Valve on H1, your main target should be Win32 - though other platforms are a viable substitute. Linux has some great tooling available and Valve regularly forgets strip is a thing on macOS (so do many other developers).

We can look at the stack trace provided by WinDBG to ascertain what’s going on.

WinDBG Stack Trace

Starting from frame 8, we’ll walk through what’s happening.

The first line of each snippet will denote where WinDBG decides the problem is.

		if ( pf->Prepare( packfile->filelen, packfile->fileofs ) )
			int nIndex;
			if ( addType == PATH_ADD_TO_TAIL )
				nIndex = m_SearchPaths.AddToTail();	
				nIndex = m_SearchPaths.AddToHead();	

			CSearchPath *sp = &m_SearchPaths[ nIndex ];

			sp->SetPackFile( pf );
			sp->m_storeId = g_iNextSearchPathID++;
			sp->SetPath( g_PathIDTable.AddString( newPath ) );
			sp->m_pPathIDInfo = FindOrAddPathIDInfo( g_PathIDTable.AddString( pPathID ), -1 );

			if ( IsDvdDevPathString( newPath ) )
				sp->m_bIsDvdDevPath = true;

			pf->SetPath( sp->GetPath() );
			pf->m_lPackFileTime = GetFileTime( newPath );

			Trace_FClose( pf->m_hPackFileHandleFS );
			pf->m_hPackFileHandleFS = NULL;

			//pf->m_PackFileID = m_FileTracker2.NotePackFileOpened( pPath, pPathID, packfile->filelen );
			m_ZipFiles.AddToTail( pf );
			delete pf;

It’s worth noting that you’re reading this correctly - LUMP_PAKFILE is simply an embedded ZIP file. There’s nothing too much of consequence here - just pointing out m_ZipFiles does indeed refer to the familiar archival format.

Frame 7 is where we start to see what’s going on.

	zipDirBuff.EnsureCapacity( rec.centralDirectorySize );
	zipDirBuff.ActivateByteSwapping( IsX360() || IsPS3() );
	ReadFromPack( -1, zipDirBuff.Base(), -1, rec.centralDirectorySize, rec.startOfCentralDirOffset );
	zipDirBuff.SeekPut( CUtlBuffer::SEEK_HEAD, rec.centralDirectorySize );

If one is to open LUMP_PAKFILE in 010 Editor and parse the file as a ZIP file, you’ll see the following.

010 Editor viewing LUMP_PAKFILE as Zipfile

elDirectorySize is our rec.centralDirectorySize, in this case. Skipping forward a frame, we can see the following.

Commented out lines highlight lines of interest.

CUtlBuffer::CUtlBuffer( int growSize, int initSize, int nFlags ) : 
	m_Memory.Init( growSize, initSize );
	m_Get = 0;
	m_Put = 0;
	m_nTab = 0;
	m_nOffset = 0;
	m_Flags = nFlags;
	if ( (initSize != 0) && !IsReadOnly() )
		m_nMaxPut = -1;
		AddNullTermination( m_Put );
		m_nMaxPut = 0;

followed by the next frame,

template< class T, class I >
void CUtlMemory<T,I>::Init( int nGrowSize /*= 0*/, int nInitSize /*= 0*/ )

	m_nGrowSize = nGrowSize;
	m_nAllocationCount = nInitSize;
	Assert( nGrowSize >= 0 );
	if (m_nAllocationCount)
		m_pMemory = (T*)malloc( m_nAllocationCount * sizeof(T) );

and finally,

inline void *MemAlloc_Alloc( size_t nSize )
	return g_pMemAlloc->IndirectAlloc( nSize );

where nSize is the value we control, or $esi. Keep in mind, this is all before the actual segfault and $eip corruption. Skipping ahead to that –

***** OUT OF MEMORY! attempted allocation size: 2425393296 ****
(311c.4ab0): Access violation - code c0000005 (first chance)
First chance exceptions are reported before any exception handling.
This exception may be expected and handled.
eax=00000032 ebx=03128f00 ecx=012fd0c0 edx=00000001 esi=012fd0c0 edi=00000000
eip=00000032 esp=012fce7c ebp=012fce88 iopl=0         nv up ei ng nz ac po nc
cs=0023  ss=002b  ds=002b  es=002b  fs=0053  gs=002b             efl=00010292
00000032 ??              ???

We’re brought to the same familiar fault. Of note is that $eax and $eip are the same value, and consistent throughout runs. If we look at the stack trace WinDBG provides, we see much of the same.

WinDBG Stack Trace

Picking apart the locals from CZipPackFile::Prepare, we can see the values on $eip and $eax repeated a few times. Namely, the tuple m_PutOverflowFunc.


So we’re able to corrupt this variable and as such, control $eax and $eip - but not to any useful extent, unfortunately. These values more or less seem arbitrary based on game version and map data. What we have, essentially - is a malloc with the value of nSize (0x90909090) with full control over the variable nSize. However, it doesn’t check if it returns a valid pointer – so the game just segfaults as we’re attempting to allocate 2 GB of memory (and returning zero.) In the end, we have a novel denial of service that does result in “control” of the instruction pointer - though not to an extent that we can pop a shell, calc, or do anything fun with it.

Thanks to mev for phrasing this better than I could.

I’d like to thank mev, another one of our members, for assisting with this writeup, alongside paracord and vmcall.

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