iOS 6
Exploitation
280
Days Later
CanSecWest Vancouver
Stefan Esser <stefan.esser@sektioneins.de>
http://www.sektioneins.de
Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 • 
Who am I?
Stefan Esser
• from Cologne / Germany
• in information security since 1998
• initially did a lot of low level security
• from 2001 to 2010 focused on PHP / web app security
• since mid-2010 focused on iPhone security (ASLR, kernel exploitation)
• Head of Research and Development at SektionEins GmbH
2
Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 • 
What is this talk about?
• iOS 6 is the new major version of iOS with tons of new security features
• new kernel security mitigations already discussed by Mark Dowd/Tarjei Mandt
• but iOS 6.x has other not yet mentioned new security features
• and some kernel features require commentary
• basically an update to my CSW 2012 talk
• 280 days later because it was about 280 days later when I submitted to Dragos
3
Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 • 
Part I
iOS Security Timeline 2012-2013
4
Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 • 
CanSecWest 2012 - iOS 5 An Exploitation Nightmare?
• reasons why iOS 5 jailbreak took so long
• history of some iOS security features
• history of iOS security bugfixes
• getting kernel debugger running
on new devices
• abusing BPF as kernel weird machine
5
March 2012
URL: http://cansecwest.com/csw12/
CSW2012_StefanEsser_iOS5_An_Exploitation_Nightmare_FINAL.pdf
Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 • 
iOS Hacker‘s Handbook
• Charlie Miller - Dionysius Blazakis - Dino Dai Zovi
• Stefan Esser - Vincenzo Iozzo - Ralf-Philipp Weinmann
• covers iOS 4 to iOS 5
• iOS Security Basics, iOS in the Enterprise
• Encryption, Code Signing and Memory Protection
• Sandboxing, Fuzzing iOS Applications
• Exploitation, Return-Oriented-Programming
• Kernel-Debugging and Exploitation, Jailbreaking, Baseband Attacks
6
April 2012
URL: http://ca.wiley.com/WileyCDA/WileyTitle/
productCd-1118204123.html
Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 • 
SyScan 2012 - iOS Kernel Heap Armageddon
• different iOS kernel heap wrappers
• feasibility of cross zone / memory manager
attacks
• attacking IOKit application data / object
vtables instead of heap meta data
• using OSUnserializeXML() for generic
kernel level heap feng shui
• talk updated for BlackHat USA & XCon 2012
7
April 2012
URL 1: http://reverse.put.as/wp-content/uploads/2011/06/
SyScan2012_StefanEsser_iOS_Kernel_Heap_Armageddon.pdf
URL 2: http://media.blackhat.com/bh-us-12/Briefings/Esser/
BH_US_12_Esser_iOS_Kernel_Heap_Armageddon_WP.pdf
Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 • 
FinFisher Mobile - The Smartphone Who Loved Me
• by CitizenLab
• analysis of FinFisher for mobile devices
• samples caught in the wild
• iOS sample compiled for developer phones
• media wrongly assumed developer cert lets
you write spy applications
8
August 2012
URL: https://citizenlab.org/2012/08/the-smartphone-who-loved-me-
finfisher-goes-mobile/
Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 • 
FinSpy Moile: iOS and Apple UDID Leak
• by Alex Radocea^Crowdstrike
• deep analysis of FinFisher for iOS
• revealed that there was no iOS priv escape
0-day in FinFisher iOS - just empty placeholder
• instead seems to heavily rely on being jailbroken
with a public jailbreak prior to installation
9
September 2012
URL: http://www.crowdstrike.com/blog/finspy-mobile-ios-and-apple-
udid-leak/index.html
Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 • 
iOS 6 Released and J/“F“ailbroken on Day 1
• by Musclenerd
• iOS 6 on pre-A5 already tethered jailbroken on day one
• by CHPWN
• iOS 6 on iPhone 5 already failbroken on day one
• failbroken means Cydia runs but no kernel payload
10
September 2012
URL: https://twitter.com/chpwn/status/249249908094296064
Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 • 
HITB2012 - iOS 6 Kernel Security
• by Mark Dowd and Tarjei Mandt
• deep analysis of new iOS 6 kernel
exploit mitigations
• contained a 0-day kernel info leak vulnerability
• and the vm_map_copy exploitation technique
heavily used by latest iOS 6 jailbreak
11
October 2012
URL: http://conference.hackinthebox.org/hitbsecconf2012kul/
materials/D1T2%20-%20Mark%20Dowd%20&%20Tarjei%20Mandt%20-
%20iOS6%20Security.pdf
Video: http://www.youtube.com/watch?v=O-WZinEoki4
Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 • 
POC2012 - Find your own iOS kernel bug
• by Xu Hao and Chen Xiaobo
• analysis of previous IOKit vulnerability
• about fuzzing iOKit for vulnerabilities
• later repeated at SyScan360 in December
12
November 2012
URL: http://syscan.org/index.php/download/get/
328bf4b37e6ae8b799472ff230465339/
XuHao_Chen_Xiaobo_Find_your_own_iOS_kernel_bug.zip
Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 • 
Hackulo.us / Installous shutdown
• announcement that Hackulo.us shut down
• also took down Installous the notorious
application used by iOS application pirates
on jailbroken iPhones
• celebrated by media, jailbreak developers
and iOS app developers around the world
13
December 2012
URL: http://thanks-god-not-anymo.re
Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 • 
kuaiyong, Zeusmos, 25pp, ...
• after installous is dead more and more iOS
piracy solutions that do not require jailbreak
• solutions reportedly based on account
sharing and/or some undisclosed exploit
• still active ?!?
14
January 2013
URL 1: http://m.csoonline.com/article/725183/now-pirated-ios-
apps-can-be-installed-without-jailbreak
URL 2: http://no.you.dont.get.the.url.you.want Research Assistant: Marc Rogers
Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 • 
Community Milking and iOS 6 JB Release
• by evad3rs
• website with donation button and
multiple banner ads
• told people repeatedly for about a week
to check website for status updates
• about one week later release of iOS 6.0/6.1 jailbreak
• so far the most expensive jailbreak in terms of crowdfunding
15
February 2013
URL: http://www.evasi0n.com/
Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 • 
evasi0n Jailbreak‘s Userland Components
• by Braden Thomas^AccuvantLabs
• analysis of userland components of
evasi0n jailbreak
• covers most of the userland bugs
exploited by evasi0n
16
February 2013
URL: http://blog.accuvantlabs.com/blog/bthomas/evasi0n-
jailbreaks-userland-component
Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 • 
Dissecting the “evasi0n“ Kernel Exploit
• by Tarjei Mandt^Azimuth
• analysis of kernel components of
evasi0n jailbreak
• shows how evasi0n is based on techniques discussed
in the iOS 6 kernel security talk by azimuth
17
February 2013
URL: http://blog.azimuthsecurity.com/2013/02/from-usr-to-svc-
dissecting-evasi0n.html
Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 • 
Part II
iOS 6 Kernel Security “Improvements“
18
Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 • 
KASLR
• iOS 6 introduces KASLR - kernel address space layout randomization
• only 256 possible load addresses
• each 2 MB apart
• starting at 0x81200000 ending at 0xA1000000
19
Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 • 
KASLR: But why 2 MB Aligned?
• 2 MB alignment of KASLR seems arbitrary
• why not smaller alignment?
• big alignment is less secure
• right now:
• leak any address in __DATA and you know the
kernel‘s base address
(address - 0x200000) & 0xFFE00000
• leak any address from first 2 MB of kernel __TEXT
and know the kernel‘s base address
address & 0xFFE00000
20
Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 • 
Kernel Address Space Hardening
• kernel __TEXT no longer writable
➡ to stop kernel code hotpatching
• kernel heap no longer executable
➡ to stop just executing kernel data
• kernel address space is separated from user space processes
➡ to stop return into user space code
and offset from NULL-deref attacks
21
Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 • 
Kernel Stack Cookies
• iOS 6 added stack cookies to protect from kernel stack
buffer overflows
• implementation is rather unusual
• stack cookie on top of stack
• bottom of local stack contains ptr to the value it is
compared against
• second byte of stack cookie is forced to 0x00
22
Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 • 
Kernel Stack Cookie Verification
23
• stack cookie verification in function epilog
• verification against cookie pointed to
• fact that stack_cookie_ptr and stack_cookie are both on stack is a weakness
• wrong cookie value will lead to a kernel panic without message
Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 • 
Kernel Heap Cookies
• iOS 4 and iOS 5 kernel heap exploitation has always attacked the free list
• in iOS 6 Apple introduced heap protection cookies to protect free list
• distinguishes between small poisoned and larger non-poisoned blocks
• two different security cookies are used for this
➡ stops attacks against the free list as used before in public jailbreaks
24
Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 • 
Kernel Heap Cookies (larger blocks)
• for larger blocks the memory content is kept but end is trashed with cookie
• secret cookie has lowest bit cleared
• if data of freed block leaks this leaks
• a kernel heap address: 0x87b46500
• the secret cookie: 0x6b7769c8 ^ 0x87b46500 = 0xECC30CC8
25
87b46480: 00 65 b4 87 00 00 00 00 00 00 00 00 00 00 00 00 .e..............
87b46490: 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 ................
87b464a0: 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 ................
87b464b0: 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 ................
87b464c0: 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 ................
87b464d0: 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 ................
87b464e0: 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 ................
87b464f0: 00 00 00 00 00 00 00 00 00 00 00 00 c8 69 77 6b .............iwk
next_pointer
next_pointer^non_poisoned_cookie
Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 • 
Kernel Heap Cookies (small blocks)
• for small blocks the memory content is overwritten with 0xdeadbeef
• secret cookie has lowest bit set
• if data of freed block leaks this leaks
• a kernel heap address: 0x92f1c740
• the secret cookie: 0x7ec1387b ^ 0x92f1c740 = 0xEC30FF3B
26
92f1c700: 40 c7 f1 92 ef be ad de ef be ad de ef be ad de @...............
92f1c710: ef be ad de ef be ad de ef be ad de ef be ad de ................
92f1c720: ef be ad de ef be ad de ef be ad de ef be ad de ................
92f1c730: ef be ad de ef be ad de ef be ad de 7b 38 c1 7e ............{8.~
next_pointer
next_pointer^poisoned_cookie
Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 • 
Kernel Heap Cookies after allocation
• on allocation free list pointer and cookie are overwritten with 0xdeadbeef
• most probably as defense in depth against information leaks
27
9072b000: ef be ad de 00 00 00 ff 00 00 00 ff 00 00 00 ff ................
9072b010: 00 00 00 ff 00 00 00 ff 00 00 00 ff 00 00 00 ff ................
9072b020: 00 00 00 ff 00 00 00 ff 00 00 00 ff 00 00 00 ff ................
9072b030: 00 00 00 ff 00 00 00 ff 00 00 00 ff 00 00 00 ff ................
9072b040: 00 00 00 ff 00 00 00 ff 00 00 00 ff 00 00 00 ff ................
9072b050: 00 00 00 ff 00 00 00 ff 00 00 00 ff 00 00 00 ff ................
9072b060: 00 00 00 ff 00 00 00 ff 00 00 00 ff 00 00 00 ff ................
9072b070: 00 00 00 ff 00 00 00 ff 00 00 00 ff ef be ad de ................
Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 • 
Kernel Heap Hardening
• previously mach_zone_info() and host_zone_info() leaked internal state
• both functions now require debugging kernel boot arguments
• previously OSUnserializeXML() allowed fine control over kernel heap
• Apple fixed some bugs in it and put some arbitrary limits on it
• only exact methods described at BlackHat / SyScan were killed
• other ways to abuse this function for kernel heap feng shui still working
28
Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 • 
Death to Kernel Info Leaks
• two fold strategy to fight kernel info leaks
• fix information leak vulnerabilities
• obfuscate kernel addresses returned to user land
• example of fixed information leaks
• BPF stack data info leak
• kern.proc leak fixed
• kern.file info leak fixed
29
Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 • 
Kernel Address Obfuscation
• lots of kernel API return kernel addresses to user land processes
e.g. mach_port_kobject(), mach_port_space_info(), vm_region_recurse(),
vm_map_region_recurse(), vm_map_page_info(), proc_info(), fstat(), sysctl()
• protected by adding a random 32 bit cookie (lowest bit set)
30
Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 • 
Kernel Image Address Obfuscation
• some API might even return addresses inside the kernel image
• these addresses are additionally unslid to protect against KASLR leaks
31
Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 • 
Readonly Syscall Table
• previous jailbreaks used partial syscall table overwrites
• Apple moved syscall table into section __DATA::__const
• section is made read only at runtime
• controlled by kernel boot argument dataconstro
• stops syscall table corruption ...
32
Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 • 
Just replace Syscall Table completely?
• kernel linking changes in iOS 6 introduced lots of indirect accesses
• syscall table is no longer accessed directly (also true for lots of other stuff)
• instead pointer to syscall table is used from __nl_symbol_ptr section
• and guess what - this section is writable
33
Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 • 
Part III
iOS 6 Misc Hardening
34
Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 • 
BPF not so weird anymore...
• at CSW 2012 BPF was mentioned as weird machine inside the kernel
• in iOS 6.x it is still a machine but not so weird anymore
• Apple added sanity checks inside the function
• access to slack memory is now checked for bounds
35
Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 • 
mobile_house_arrest - Readonly Code Directory
• lockdown service for reading / writing into app directories
• since iOS 6 application‘s code directory is no longer writable
• previously it was possible to replace arbitrary application resources
36
Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 • 
Part IV
User Space ASLR (Address Space Layout Randomization)
37
Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 • 
ASLR in iOS 4.3-6.x
• randomly slides
• main binary
• dyld (dynamic linker)
• dynamic library cache
38
Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 • 
Position Independent Executables in 2012
• all system binaries were
compiled as PIE
• most 3rd party apps were
not compiled as PIE
39
$ python ipapiescan.py
Adobe Reader - armv7 - PIE - N/A
Bluefire Reader - armv6|armv7 - NO_PIE - 3.0
DiamondDash - armv7 - NO_PIE - 4.2
Ebook Reader - armv6|armv7 - NO_PIE - N/A
eBookS Reader - armv6|armv7 - NO_PIE - N/A
Facebook - armv6|armv7 - NO_PIE - 4.0
Fly With Me - armv6|armv7 - NO_PIE - 3.0
FPK Reader - armv6|armv7 - NO_PIE - 3.2
Hotels - armv6|armv7 - NO_PIE - 3.1
iBooks - armv6|armv7 - NO_PIE - 4.2
KakaoTalk - armv6|armv7 - NO_PIE - 3.1
Messenger - armv6|armv7 - NO_PIE - 4.0
PerfectReader Mini - armv6|armv7 - NO_PIE - N/A
QR Reader - armv6|armv7 - NO_PIE - 4.0
QR Scanner - armv6|armv7 - NO_PIE - N/A
QR-Scanner - armv7 - NO_PIE - 4.0
QRCode - armv6|armv7 - NO_PIE - N/A
Quick Scan - armv6|armv7 - NO_PIE - 4.0
Skype - armv6|armv7 - NO_PIE - N/A
Twitter - armv6|armv7 - NO_PIE - 4.0
vBookz PDF - armv7 - PIE - 4.3
VZ-Netzwerke - armv6 - NO_PIE - 3.0
Wallpapers - armv6|armv7 - NO_PIE - 4.1
WhatsApp - armv6|armv7 - NO_PIE - 3.1
Where is - armv6|armv7 - NO_PIE - 4.1
source code of old idapiescan.py is available at Github
https://github.com/stefanesser/idapiescan
Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 • 
iOS 4.3-6.x: NO PIE main binary randomization
• dynamic loader is not slid in iOS 4 for NO PIE main executables
• since iOS 5 the dynamic loader is always slid
• randomized by kernel in 256 positions
40
iOS 4.3 - 4.3.x - NO PIE main executable
iOS 5.0 - 6.x - NO PIE main executable
Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 • 
Position Independent Executables in 2013
• all system binaries are
compiled as PIE
• most 3rd party apps are
now compiled as PIE
• NO_PIE mostly
unimportant apps
• some high profile
exceptions are: Skype,
SkyDrive,
Google Translate, ...
41
$ python ipapiescan.py
Bluefire Reader - armv7(s) - PIE - 4.3
Calendar Pro - armv7(s) - PIE - 4.3
CalenMob - armv7(s) - PIE - 5.0
Chrome - armv7 - PIE - 4.3
CloudOn - armv7 - NO_PIE - 5.0
DiamondDash - armv7(s) - PIE - 4.3
Documents - armv7(s) - PIE - 4.3
Ebook Reader - armv7 - PIE - 4.3
eBookS Reader - armv6|armv7 - NO_PIE - N/A
Facebook - armv7 - PIE - 4.3
G-Whizz! - armv6|armv7 - NO_PIE - 4.0
Gmail - armv7 - PIE - 5.0
Google - armv7 - PIE - 4.3
Google Drive - armv7 - PIE - 5.0
Google Earth - armv7 - PIE - 4.3
Google+ - armv7 - PIE - 5.0
iBooks - armv7 - PIE - 5.0
IM+ - armv7(s) - PIE - 4.3
Instagram - armv7 - PIE - 4.3
KakaoTalk - armv7(s) - PIE - 4.3
Latitude - armv6|armv7 - NO_PIE - N/A
Local - armv6|armv7 - PIE - 4.3
Lync 2010 - armv7 - NO_PIE - 4.3
Messenger - armv7 - PIE - 4.3
MSN World - armv7(s) - PIE - 4.3
SkyDrive - armv6|armv7 - NO_PIE - 4.0
Skype - armv7 - NO_PIE - 4.3
SmartGlass - armv7 - PIE - 5.0
SSH Mobile Free - armv7(s) - PIE - 4.3
SystemTools - armv7(s) - PIE - 4.3
Translate - armv6|armv7 - NO_PIE - N/A
Trillian - armv7 - PIE - 4.3
Twitter - armv7 - PIE - 5.0
Usessh - armv7(s) - PIE - 4.3
Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 • 
iOS 4.3-6.0: PIE main binary randomization
• for PIE main executables the main binary and dyld are randomized
• main binary and dyld are slid the same amount
• randomized by kernel in 256 positions
42
iOS 4.3 - 6.0 - PIE main executable
Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 • 
iOS 6.1: PIE main binary randomization
• since iOS 6.1 the kernel finally generates two separate slides
• randomness of both is still limited to 256 positions
• knowing addresses in dyld / main no longer leaks address of other
43
iOS 4.3 - 6.0 - PIE main executable
iOS 6.1 - PIE main executable
Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 • 
iOS 4.3-5.1.1: dyld_shared_cache randomization
• data and code must slide together (due to codesigning)
• hole after code - data usually loaded to 0x3E000000
• max slide determined by difference of end of shared area and end of data
• around 4200 different positions
44
iOS 4.3 - 5.1.1 - maximum slide
iOS 4.3 - 5.1.1 - no slide
Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 • 
iOS 6.x: dyld_shared_cache randomization
• code and data loaded right next to each other
• no more hole - no more wasted space
• max slide determined by size of shared area minus size of shared cache
• about 21500 different positions for iPod 4G
(new devices = more code = less random)
45
iOS 6.x - no slide
iOS 6.x - maximum slide
Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 • 
Part V
iOS 6 and the Partial Code-signing Vulnerability
46
Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 • 
Partial Code-signing Vulnerability (iOS 4)
• in iOS 4.x jailbreaks the method of choice to launch untether exploits
• when a mach-o is loaded the kernel will load it as is
• a possible signature will be registered
• missing signature is okay until a not signed executable page is accessed
• dyld was tricked with malformed mach-o data structures to execute code
47
Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 • 
sniffLoadCommands (iOS 4.3.4)
• function does pre-handling of mach-o load commands
• iOS 4.3.4 adds protection against partial code signing
• mach-o load commands must be inside a segment
• mach-o load commands can only be in R + X segment
• mach-o load commands may not be partially in a segment
➡ effect is that once dyld maps the header R+X it can only continue to work on it if there is a valid signature
48
Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 • 
Partial Code-signing Vuln (iOS 4.3.4-iOS 5.1.1)
• protection in sniffLoadCommands could be bypassed
• by having a RW- LC_SEGMENT64 for mach-o header
• and a fake R-X LC_SEGMENT for mach-o header
• disclosed at CanSecWest 2012 - here on stage
• worked because kernel handles LC_SEGMENT64 and dyld did not
• magic is that dyld will read mach-o header from from address in memory
49
Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 • 
sniffLoadCommands (iOS 6.0)
• iOS 6.0 adds protection against CSW 2012 trick to sniffLoadCommands
• if a LC_SEGMENT64 load command is found an exception is thrown
➡ CSW 2012 trick was already partially broken after iOS 5.1.1
• in iOS 5.1.1 AMFI verified existence of a code signing blob
50
Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 • 
Load Command Segment Override (iOS 6.0-6.1.2)
• bug used by evasi0n
• kernel not directly involved in loading dynamic libraries only dyld is
• dyld could be tricked with a malicious dylib
• contains real R-X segment with load commands in it
• contains second R-- segment that contains copy of load commands
• virtual address of both segments is set to same position
• later segment in mach-o will replace previous in memory
• when dyld accesses header it is in RO memory = no sig needed = bypass
51
Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 • 
sniffLoadCommands (iOS 6.1.3 beta 2)
• iOS 6.1.3 beta 2 adds additional protections to sniffLoadCommands
• load commands must now be in one segment only
• for dynamic libraries a second sniff pass is added
• all segments must not intersect the R-X segment containing the load
commands
➡ evasi0n untether killed
52
Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 • 
Part VI
iOS 6.1 and Launch-Daemon-Code-Signing
53
Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 • 
Launch Daemons to launch Untethers
• in iOS 5.x jailbreaks were launched on boot via launch daemons
• launch daemons are plists describing system services
54
<?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>Label</key>
<string>jb</string>
<key>ProgramArguments</key>
<array>
<string>/usr/sbin/corona</string>
<string>-f</string>
<string>racoon-exploit.conf</string>
</array>
<key>WorkingDirectory</key>
<string>/usr/share/corona/</string>
<key>RunAtLoad</key>
<true/>
<key>LaunchOnlyOnce</key>
<true/>
<key>DisableAslr</key>
<true/>
</dict>
</plist>
DisableAslr was removed from iOS 5.1
Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 • 
Launch-Daemon-Code-Signing (I)
55
• abuse of launch daemons lead
to new iOS 6.1 security feature
• launch daemon loading is now
code signed
• implemented in /bin/launchctl
• can be bypassed by setting
kernel boot arguments
(not possible without low-level exploit)
Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 • 
Launch-Daemon-Code-Signing (II)
56
• without launch-daemon-code-signing
/bin/launchctl scans /System/Library/LaunchDaemons for defined
launch daemons and loads them
• with activated launch-daemon-code-signing
a big plist with all defined launch daemons is loaded instead
• launch daemon can only be loaded if it is defined in the plist and exists on disk
Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 • 
Launch-Daemon-Code-Signing (III)
57
• big launch daemon plist is loaded from
/System/Library/Caches/com.apple.xpcd/xpcd_cache.dylib
• this dynamic library is within the dyld_shared_cache and therefore code signed
• symbol __xpcd_cache must exist
• but binary plist is take from sectiondata of __TEXT::__xpcd_cache
Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 • 
XPCD_CACHE.PLIST
58
Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 • 
Launch-Daemon-Code-Signing Security
59
How secure Apple wanted Launch-Daemon-Code-Signing to be...
Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 • 
Launch-Daemon-Code-Signing Security
60
How secure Launch-Daemon-Code-Signing is right now...
Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 • 
Launch-Daemon-Code-Signing Security
• code signing itself seems to stop loading arbitrary launch daemons
• but Apple forgot / or ignored /etc/launchd.conf
• /etc/launchd.conf defines commands launchctl executes on start
• attacker can execute arbitrary existing commands
61
bsexec .. /sbin/mount -u -o rw,suid,dev /
setenv DYLD_INSERT_LIBRARIES /private/var/evasi0n/amfi.dylib
load /System/Library/LaunchDaemons/com.apple.MobileFileIntegrity.plist
bsexec .. /private/var/evasi0n/evasi0n
unsetenv DYLD_INSERT_LIBRARIES
bsexec .. /bin/rm -f /private/var/evasi0n/sock
bsexec .. /bin/ln -f /var/tmp/launchd/sock /private/var/evasi0n/sock
Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 • 
FAQ: Why not put old launchctl binary on device?
Q: “If only the newest iOS 6.1 launchctl binary
implements this code signing. Why not put an iOS 6.0
launchctl binary on the device to bypass this protection?“
A: “System binaries like launchctl do not come with a valid code signing
signature from Apple. Instead they come only with the table of memory page
hashes and entitlements. When the kernel loads such a binary it hashes these
tables and checks if the hash is in a whitelist inside the kernel (a.k.a. trust cache).
The old launchctl binary will not be accepted because it is not in the trust cache
of the new kernel.“
62
Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 • 
Final Words
• with iOS 6 Apple has tried to kill all public techniques
• finally kills some stuff that was previously known and ignored for 10 years
• the new mitigations make exploitation a lot harder
• when launch daemon code signing is hardened a bit more,
persisting on iDevices will become incredibly hard
• however there are still weaknesses in most of the protections
• ... and tons of kernel information leaks
63
Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 • 
Questions
?
64

More Related Content

PPT
Mobile Security Assessment: 101
PDF
Iphone Presentation for MuMe09
PDF
I Want More Ninja – iOS Security Testing
PPT
iOS Hacking: Advanced Pentest & Forensic Techniques
PPTX
Hacking and securing ios applications
PDF
Hacking and Securing iOS Apps : Part 1
PDF
OWASP Melbourne - Introduction to iOS Application Penetration Testing
PPT
Jail breaking
Mobile Security Assessment: 101
Iphone Presentation for MuMe09
I Want More Ninja – iOS Security Testing
iOS Hacking: Advanced Pentest & Forensic Techniques
Hacking and securing ios applications
Hacking and Securing iOS Apps : Part 1
OWASP Melbourne - Introduction to iOS Application Penetration Testing
Jail breaking

What's hot (20)

PDF
Mobile Device Encryption Systems
PDF
iOS Application Penetration Testing
PPTX
Android vs iOS encryption systems
PDF
When Encryption is Not Enough...Sumanth Naropanth, Chandra Prakash Gopalaiah ...
PDF
Dark Side of iOS [SmartDevCon 2013]
PDF
Troopers14 Advanced Smartphone forensics - Vladimir Katalov
PPTX
Ярослав Воронцов — Пара слов о mobile security.
PDF
Android Security - Common Security Pitfalls in Android Applications
PDF
IOS Encryption Systems
PDF
Никита Корчагин - Introduction to Apple iOS Development.
PPTX
Which Mobile OS is the Most Secure; Apple, Android or Windows? [Updated 2016-...
PDF
Android system security
PPTX
Help Doctor, my application is an onion!
PPTX
Apple iOS
PDF
Android Security
PDF
The Android vs. Apple iOS Security Showdown
PDF
Android App Hacking - Erez Metula, AppSec
PDF
CNIT 128: Android Implementation Issues (Part 2)
PPTX
iOS platform
PPTX
[Wroclaw #1] Android Security Workshop
Mobile Device Encryption Systems
iOS Application Penetration Testing
Android vs iOS encryption systems
When Encryption is Not Enough...Sumanth Naropanth, Chandra Prakash Gopalaiah ...
Dark Side of iOS [SmartDevCon 2013]
Troopers14 Advanced Smartphone forensics - Vladimir Katalov
Ярослав Воронцов — Пара слов о mobile security.
Android Security - Common Security Pitfalls in Android Applications
IOS Encryption Systems
Никита Корчагин - Introduction to Apple iOS Development.
Which Mobile OS is the Most Secure; Apple, Android or Windows? [Updated 2016-...
Android system security
Help Doctor, my application is an onion!
Apple iOS
Android Security
The Android vs. Apple iOS Security Showdown
Android App Hacking - Erez Metula, AppSec
CNIT 128: Android Implementation Issues (Part 2)
iOS platform
[Wroclaw #1] Android Security Workshop
Ad

Viewers also liked (10)

PDF
Dconf2015 d2 t4
PDF
Three Optimization Tips for C++
PDF
Three Optimization Tips for C++
PDF
Deep C Programming
PPTX
PDF
C++ idioms by example (Nov 2008)
PDF
Solid C++ by Example
PDF
Insecure coding in C (and C++)
PDF
TDD in C - Recently Used List Kata
PDF
Deep C
Dconf2015 d2 t4
Three Optimization Tips for C++
Three Optimization Tips for C++
Deep C Programming
C++ idioms by example (Nov 2008)
Solid C++ by Example
Insecure coding in C (and C++)
TDD in C - Recently Used List Kata
Deep C
Ad

Similar to iOS 6 Exploitation 280 days later (20)

PDF
iOS 6 Exploitation: 280 days later
PDF
CanSecWest 2013 - iOS 6 Exploitation 280 Days Later
PDF
SyScan 2015 - iOS 678 Security - A Study in Fail
PDF
Antid0te 2.0 – ASLR in iOS
PDF
Attacking and Defending Apple iOS Devices
PDF
Targeting the iOS kernel
PDF
SyScan Singapore 2011 - Stefan Esser - Targeting the iOS Kernel
PDF
iOS Application Penetation Test
PPT
CocoaHeads Toulouse - iOS TechTalk - Mélanie Bessagnet
PDF
Ruxmon April 2014 - Introduction to iOS Penetration Testing
PDF
Bad for Enterprise: Attacking BYOD enterprise mobility security solutions
PDF
A (not-so-quick) Primer on iOS Encryption David Schuetz - NCC Group
PPTX
[OWASP Poland Day] Saving private token
PPTX
azure synapse analytics end-to-end solution-hands-on at 20200728
PDF
Ruxcon 2014 - Stefan Esser - iOS8 Containers, Sandboxes and Entitlements
PDF
CNIT 128 2. Analyzing iOS Applications (Part 1)
PDF
(130622) #fitalk i cloud keychain forensics
PDF
2a Analyzing iOS Apps Part 1
PDF
iOS Forensics: where are we now and what are we missing?
PPTX
Forensics WS Consolidated
iOS 6 Exploitation: 280 days later
CanSecWest 2013 - iOS 6 Exploitation 280 Days Later
SyScan 2015 - iOS 678 Security - A Study in Fail
Antid0te 2.0 – ASLR in iOS
Attacking and Defending Apple iOS Devices
Targeting the iOS kernel
SyScan Singapore 2011 - Stefan Esser - Targeting the iOS Kernel
iOS Application Penetation Test
CocoaHeads Toulouse - iOS TechTalk - Mélanie Bessagnet
Ruxmon April 2014 - Introduction to iOS Penetration Testing
Bad for Enterprise: Attacking BYOD enterprise mobility security solutions
A (not-so-quick) Primer on iOS Encryption David Schuetz - NCC Group
[OWASP Poland Day] Saving private token
azure synapse analytics end-to-end solution-hands-on at 20200728
Ruxcon 2014 - Stefan Esser - iOS8 Containers, Sandboxes and Entitlements
CNIT 128 2. Analyzing iOS Applications (Part 1)
(130622) #fitalk i cloud keychain forensics
2a Analyzing iOS Apps Part 1
iOS Forensics: where are we now and what are we missing?
Forensics WS Consolidated

Recently uploaded (20)

PDF
Hybrid horned lizard optimization algorithm-aquila optimizer for DC motor
PPTX
AI IN MARKETING- PRESENTED BY ANWAR KABIR 1st June 2025.pptx
PDF
Developing a website for English-speaking practice to English as a foreign la...
PDF
Consumable AI The What, Why & How for Small Teams.pdf
PDF
Architecture types and enterprise applications.pdf
PDF
Convolutional neural network based encoder-decoder for efficient real-time ob...
PDF
How IoT Sensor Integration in 2025 is Transforming Industries Worldwide
PDF
CloudStack 4.21: First Look Webinar slides
PDF
Comparative analysis of machine learning models for fake news detection in so...
PPTX
The various Industrial Revolutions .pptx
PPTX
Chapter 5: Probability Theory and Statistics
PPT
Galois Field Theory of Risk: A Perspective, Protocol, and Mathematical Backgr...
PPTX
Microsoft Excel 365/2024 Beginner's training
PDF
Zenith AI: Advanced Artificial Intelligence
PDF
NewMind AI Weekly Chronicles – August ’25 Week III
DOCX
search engine optimization ppt fir known well about this
PPTX
Final SEM Unit 1 for mit wpu at pune .pptx
PDF
Enhancing plagiarism detection using data pre-processing and machine learning...
PDF
Taming the Chaos: How to Turn Unstructured Data into Decisions
PDF
OpenACC and Open Hackathons Monthly Highlights July 2025
Hybrid horned lizard optimization algorithm-aquila optimizer for DC motor
AI IN MARKETING- PRESENTED BY ANWAR KABIR 1st June 2025.pptx
Developing a website for English-speaking practice to English as a foreign la...
Consumable AI The What, Why & How for Small Teams.pdf
Architecture types and enterprise applications.pdf
Convolutional neural network based encoder-decoder for efficient real-time ob...
How IoT Sensor Integration in 2025 is Transforming Industries Worldwide
CloudStack 4.21: First Look Webinar slides
Comparative analysis of machine learning models for fake news detection in so...
The various Industrial Revolutions .pptx
Chapter 5: Probability Theory and Statistics
Galois Field Theory of Risk: A Perspective, Protocol, and Mathematical Backgr...
Microsoft Excel 365/2024 Beginner's training
Zenith AI: Advanced Artificial Intelligence
NewMind AI Weekly Chronicles – August ’25 Week III
search engine optimization ppt fir known well about this
Final SEM Unit 1 for mit wpu at pune .pptx
Enhancing plagiarism detection using data pre-processing and machine learning...
Taming the Chaos: How to Turn Unstructured Data into Decisions
OpenACC and Open Hackathons Monthly Highlights July 2025

iOS 6 Exploitation 280 days later

  • 1. iOS 6 Exploitation 280 Days Later CanSecWest Vancouver Stefan Esser <stefan.esser@sektioneins.de> http://www.sektioneins.de
  • 2. Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 •  Who am I? Stefan Esser • from Cologne / Germany • in information security since 1998 • initially did a lot of low level security • from 2001 to 2010 focused on PHP / web app security • since mid-2010 focused on iPhone security (ASLR, kernel exploitation) • Head of Research and Development at SektionEins GmbH 2
  • 3. Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 •  What is this talk about? • iOS 6 is the new major version of iOS with tons of new security features • new kernel security mitigations already discussed by Mark Dowd/Tarjei Mandt • but iOS 6.x has other not yet mentioned new security features • and some kernel features require commentary • basically an update to my CSW 2012 talk • 280 days later because it was about 280 days later when I submitted to Dragos 3
  • 4. Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 •  Part I iOS Security Timeline 2012-2013 4
  • 5. Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 •  CanSecWest 2012 - iOS 5 An Exploitation Nightmare? • reasons why iOS 5 jailbreak took so long • history of some iOS security features • history of iOS security bugfixes • getting kernel debugger running on new devices • abusing BPF as kernel weird machine 5 March 2012 URL: http://cansecwest.com/csw12/ CSW2012_StefanEsser_iOS5_An_Exploitation_Nightmare_FINAL.pdf
  • 6. Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 •  iOS Hacker‘s Handbook • Charlie Miller - Dionysius Blazakis - Dino Dai Zovi • Stefan Esser - Vincenzo Iozzo - Ralf-Philipp Weinmann • covers iOS 4 to iOS 5 • iOS Security Basics, iOS in the Enterprise • Encryption, Code Signing and Memory Protection • Sandboxing, Fuzzing iOS Applications • Exploitation, Return-Oriented-Programming • Kernel-Debugging and Exploitation, Jailbreaking, Baseband Attacks 6 April 2012 URL: http://ca.wiley.com/WileyCDA/WileyTitle/ productCd-1118204123.html
  • 7. Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 •  SyScan 2012 - iOS Kernel Heap Armageddon • different iOS kernel heap wrappers • feasibility of cross zone / memory manager attacks • attacking IOKit application data / object vtables instead of heap meta data • using OSUnserializeXML() for generic kernel level heap feng shui • talk updated for BlackHat USA & XCon 2012 7 April 2012 URL 1: http://reverse.put.as/wp-content/uploads/2011/06/ SyScan2012_StefanEsser_iOS_Kernel_Heap_Armageddon.pdf URL 2: http://media.blackhat.com/bh-us-12/Briefings/Esser/ BH_US_12_Esser_iOS_Kernel_Heap_Armageddon_WP.pdf
  • 8. Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 •  FinFisher Mobile - The Smartphone Who Loved Me • by CitizenLab • analysis of FinFisher for mobile devices • samples caught in the wild • iOS sample compiled for developer phones • media wrongly assumed developer cert lets you write spy applications 8 August 2012 URL: https://citizenlab.org/2012/08/the-smartphone-who-loved-me- finfisher-goes-mobile/
  • 9. Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 •  FinSpy Moile: iOS and Apple UDID Leak • by Alex Radocea^Crowdstrike • deep analysis of FinFisher for iOS • revealed that there was no iOS priv escape 0-day in FinFisher iOS - just empty placeholder • instead seems to heavily rely on being jailbroken with a public jailbreak prior to installation 9 September 2012 URL: http://www.crowdstrike.com/blog/finspy-mobile-ios-and-apple- udid-leak/index.html
  • 10. Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 •  iOS 6 Released and J/“F“ailbroken on Day 1 • by Musclenerd • iOS 6 on pre-A5 already tethered jailbroken on day one • by CHPWN • iOS 6 on iPhone 5 already failbroken on day one • failbroken means Cydia runs but no kernel payload 10 September 2012 URL: https://twitter.com/chpwn/status/249249908094296064
  • 11. Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 •  HITB2012 - iOS 6 Kernel Security • by Mark Dowd and Tarjei Mandt • deep analysis of new iOS 6 kernel exploit mitigations • contained a 0-day kernel info leak vulnerability • and the vm_map_copy exploitation technique heavily used by latest iOS 6 jailbreak 11 October 2012 URL: http://conference.hackinthebox.org/hitbsecconf2012kul/ materials/D1T2%20-%20Mark%20Dowd%20&%20Tarjei%20Mandt%20- %20iOS6%20Security.pdf Video: http://www.youtube.com/watch?v=O-WZinEoki4
  • 12. Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 •  POC2012 - Find your own iOS kernel bug • by Xu Hao and Chen Xiaobo • analysis of previous IOKit vulnerability • about fuzzing iOKit for vulnerabilities • later repeated at SyScan360 in December 12 November 2012 URL: http://syscan.org/index.php/download/get/ 328bf4b37e6ae8b799472ff230465339/ XuHao_Chen_Xiaobo_Find_your_own_iOS_kernel_bug.zip
  • 13. Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 •  Hackulo.us / Installous shutdown • announcement that Hackulo.us shut down • also took down Installous the notorious application used by iOS application pirates on jailbroken iPhones • celebrated by media, jailbreak developers and iOS app developers around the world 13 December 2012 URL: http://thanks-god-not-anymo.re
  • 14. Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 •  kuaiyong, Zeusmos, 25pp, ... • after installous is dead more and more iOS piracy solutions that do not require jailbreak • solutions reportedly based on account sharing and/or some undisclosed exploit • still active ?!? 14 January 2013 URL 1: http://m.csoonline.com/article/725183/now-pirated-ios- apps-can-be-installed-without-jailbreak URL 2: http://no.you.dont.get.the.url.you.want Research Assistant: Marc Rogers
  • 15. Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 •  Community Milking and iOS 6 JB Release • by evad3rs • website with donation button and multiple banner ads • told people repeatedly for about a week to check website for status updates • about one week later release of iOS 6.0/6.1 jailbreak • so far the most expensive jailbreak in terms of crowdfunding 15 February 2013 URL: http://www.evasi0n.com/
  • 16. Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 •  evasi0n Jailbreak‘s Userland Components • by Braden Thomas^AccuvantLabs • analysis of userland components of evasi0n jailbreak • covers most of the userland bugs exploited by evasi0n 16 February 2013 URL: http://blog.accuvantlabs.com/blog/bthomas/evasi0n- jailbreaks-userland-component
  • 17. Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 •  Dissecting the “evasi0n“ Kernel Exploit • by Tarjei Mandt^Azimuth • analysis of kernel components of evasi0n jailbreak • shows how evasi0n is based on techniques discussed in the iOS 6 kernel security talk by azimuth 17 February 2013 URL: http://blog.azimuthsecurity.com/2013/02/from-usr-to-svc- dissecting-evasi0n.html
  • 18. Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 •  Part II iOS 6 Kernel Security “Improvements“ 18
  • 19. Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 •  KASLR • iOS 6 introduces KASLR - kernel address space layout randomization • only 256 possible load addresses • each 2 MB apart • starting at 0x81200000 ending at 0xA1000000 19
  • 20. Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 •  KASLR: But why 2 MB Aligned? • 2 MB alignment of KASLR seems arbitrary • why not smaller alignment? • big alignment is less secure • right now: • leak any address in __DATA and you know the kernel‘s base address (address - 0x200000) & 0xFFE00000 • leak any address from first 2 MB of kernel __TEXT and know the kernel‘s base address address & 0xFFE00000 20
  • 21. Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 •  Kernel Address Space Hardening • kernel __TEXT no longer writable ➡ to stop kernel code hotpatching • kernel heap no longer executable ➡ to stop just executing kernel data • kernel address space is separated from user space processes ➡ to stop return into user space code and offset from NULL-deref attacks 21
  • 22. Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 •  Kernel Stack Cookies • iOS 6 added stack cookies to protect from kernel stack buffer overflows • implementation is rather unusual • stack cookie on top of stack • bottom of local stack contains ptr to the value it is compared against • second byte of stack cookie is forced to 0x00 22
  • 23. Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 •  Kernel Stack Cookie Verification 23 • stack cookie verification in function epilog • verification against cookie pointed to • fact that stack_cookie_ptr and stack_cookie are both on stack is a weakness • wrong cookie value will lead to a kernel panic without message
  • 24. Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 •  Kernel Heap Cookies • iOS 4 and iOS 5 kernel heap exploitation has always attacked the free list • in iOS 6 Apple introduced heap protection cookies to protect free list • distinguishes between small poisoned and larger non-poisoned blocks • two different security cookies are used for this ➡ stops attacks against the free list as used before in public jailbreaks 24
  • 25. Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 •  Kernel Heap Cookies (larger blocks) • for larger blocks the memory content is kept but end is trashed with cookie • secret cookie has lowest bit cleared • if data of freed block leaks this leaks • a kernel heap address: 0x87b46500 • the secret cookie: 0x6b7769c8 ^ 0x87b46500 = 0xECC30CC8 25 87b46480: 00 65 b4 87 00 00 00 00 00 00 00 00 00 00 00 00 .e.............. 87b46490: 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 ................ 87b464a0: 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 ................ 87b464b0: 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 ................ 87b464c0: 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 ................ 87b464d0: 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 ................ 87b464e0: 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 00 ................ 87b464f0: 00 00 00 00 00 00 00 00 00 00 00 00 c8 69 77 6b .............iwk next_pointer next_pointer^non_poisoned_cookie
  • 26. Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 •  Kernel Heap Cookies (small blocks) • for small blocks the memory content is overwritten with 0xdeadbeef • secret cookie has lowest bit set • if data of freed block leaks this leaks • a kernel heap address: 0x92f1c740 • the secret cookie: 0x7ec1387b ^ 0x92f1c740 = 0xEC30FF3B 26 92f1c700: 40 c7 f1 92 ef be ad de ef be ad de ef be ad de @............... 92f1c710: ef be ad de ef be ad de ef be ad de ef be ad de ................ 92f1c720: ef be ad de ef be ad de ef be ad de ef be ad de ................ 92f1c730: ef be ad de ef be ad de ef be ad de 7b 38 c1 7e ............{8.~ next_pointer next_pointer^poisoned_cookie
  • 27. Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 •  Kernel Heap Cookies after allocation • on allocation free list pointer and cookie are overwritten with 0xdeadbeef • most probably as defense in depth against information leaks 27 9072b000: ef be ad de 00 00 00 ff 00 00 00 ff 00 00 00 ff ................ 9072b010: 00 00 00 ff 00 00 00 ff 00 00 00 ff 00 00 00 ff ................ 9072b020: 00 00 00 ff 00 00 00 ff 00 00 00 ff 00 00 00 ff ................ 9072b030: 00 00 00 ff 00 00 00 ff 00 00 00 ff 00 00 00 ff ................ 9072b040: 00 00 00 ff 00 00 00 ff 00 00 00 ff 00 00 00 ff ................ 9072b050: 00 00 00 ff 00 00 00 ff 00 00 00 ff 00 00 00 ff ................ 9072b060: 00 00 00 ff 00 00 00 ff 00 00 00 ff 00 00 00 ff ................ 9072b070: 00 00 00 ff 00 00 00 ff 00 00 00 ff ef be ad de ................
  • 28. Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 •  Kernel Heap Hardening • previously mach_zone_info() and host_zone_info() leaked internal state • both functions now require debugging kernel boot arguments • previously OSUnserializeXML() allowed fine control over kernel heap • Apple fixed some bugs in it and put some arbitrary limits on it • only exact methods described at BlackHat / SyScan were killed • other ways to abuse this function for kernel heap feng shui still working 28
  • 29. Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 •  Death to Kernel Info Leaks • two fold strategy to fight kernel info leaks • fix information leak vulnerabilities • obfuscate kernel addresses returned to user land • example of fixed information leaks • BPF stack data info leak • kern.proc leak fixed • kern.file info leak fixed 29
  • 30. Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 •  Kernel Address Obfuscation • lots of kernel API return kernel addresses to user land processes e.g. mach_port_kobject(), mach_port_space_info(), vm_region_recurse(), vm_map_region_recurse(), vm_map_page_info(), proc_info(), fstat(), sysctl() • protected by adding a random 32 bit cookie (lowest bit set) 30
  • 31. Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 •  Kernel Image Address Obfuscation • some API might even return addresses inside the kernel image • these addresses are additionally unslid to protect against KASLR leaks 31
  • 32. Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 •  Readonly Syscall Table • previous jailbreaks used partial syscall table overwrites • Apple moved syscall table into section __DATA::__const • section is made read only at runtime • controlled by kernel boot argument dataconstro • stops syscall table corruption ... 32
  • 33. Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 •  Just replace Syscall Table completely? • kernel linking changes in iOS 6 introduced lots of indirect accesses • syscall table is no longer accessed directly (also true for lots of other stuff) • instead pointer to syscall table is used from __nl_symbol_ptr section • and guess what - this section is writable 33
  • 34. Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 •  Part III iOS 6 Misc Hardening 34
  • 35. Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 •  BPF not so weird anymore... • at CSW 2012 BPF was mentioned as weird machine inside the kernel • in iOS 6.x it is still a machine but not so weird anymore • Apple added sanity checks inside the function • access to slack memory is now checked for bounds 35
  • 36. Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 •  mobile_house_arrest - Readonly Code Directory • lockdown service for reading / writing into app directories • since iOS 6 application‘s code directory is no longer writable • previously it was possible to replace arbitrary application resources 36
  • 37. Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 •  Part IV User Space ASLR (Address Space Layout Randomization) 37
  • 38. Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 •  ASLR in iOS 4.3-6.x • randomly slides • main binary • dyld (dynamic linker) • dynamic library cache 38
  • 39. Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 •  Position Independent Executables in 2012 • all system binaries were compiled as PIE • most 3rd party apps were not compiled as PIE 39 $ python ipapiescan.py Adobe Reader - armv7 - PIE - N/A Bluefire Reader - armv6|armv7 - NO_PIE - 3.0 DiamondDash - armv7 - NO_PIE - 4.2 Ebook Reader - armv6|armv7 - NO_PIE - N/A eBookS Reader - armv6|armv7 - NO_PIE - N/A Facebook - armv6|armv7 - NO_PIE - 4.0 Fly With Me - armv6|armv7 - NO_PIE - 3.0 FPK Reader - armv6|armv7 - NO_PIE - 3.2 Hotels - armv6|armv7 - NO_PIE - 3.1 iBooks - armv6|armv7 - NO_PIE - 4.2 KakaoTalk - armv6|armv7 - NO_PIE - 3.1 Messenger - armv6|armv7 - NO_PIE - 4.0 PerfectReader Mini - armv6|armv7 - NO_PIE - N/A QR Reader - armv6|armv7 - NO_PIE - 4.0 QR Scanner - armv6|armv7 - NO_PIE - N/A QR-Scanner - armv7 - NO_PIE - 4.0 QRCode - armv6|armv7 - NO_PIE - N/A Quick Scan - armv6|armv7 - NO_PIE - 4.0 Skype - armv6|armv7 - NO_PIE - N/A Twitter - armv6|armv7 - NO_PIE - 4.0 vBookz PDF - armv7 - PIE - 4.3 VZ-Netzwerke - armv6 - NO_PIE - 3.0 Wallpapers - armv6|armv7 - NO_PIE - 4.1 WhatsApp - armv6|armv7 - NO_PIE - 3.1 Where is - armv6|armv7 - NO_PIE - 4.1 source code of old idapiescan.py is available at Github https://github.com/stefanesser/idapiescan
  • 40. Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 •  iOS 4.3-6.x: NO PIE main binary randomization • dynamic loader is not slid in iOS 4 for NO PIE main executables • since iOS 5 the dynamic loader is always slid • randomized by kernel in 256 positions 40 iOS 4.3 - 4.3.x - NO PIE main executable iOS 5.0 - 6.x - NO PIE main executable
  • 41. Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 •  Position Independent Executables in 2013 • all system binaries are compiled as PIE • most 3rd party apps are now compiled as PIE • NO_PIE mostly unimportant apps • some high profile exceptions are: Skype, SkyDrive, Google Translate, ... 41 $ python ipapiescan.py Bluefire Reader - armv7(s) - PIE - 4.3 Calendar Pro - armv7(s) - PIE - 4.3 CalenMob - armv7(s) - PIE - 5.0 Chrome - armv7 - PIE - 4.3 CloudOn - armv7 - NO_PIE - 5.0 DiamondDash - armv7(s) - PIE - 4.3 Documents - armv7(s) - PIE - 4.3 Ebook Reader - armv7 - PIE - 4.3 eBookS Reader - armv6|armv7 - NO_PIE - N/A Facebook - armv7 - PIE - 4.3 G-Whizz! - armv6|armv7 - NO_PIE - 4.0 Gmail - armv7 - PIE - 5.0 Google - armv7 - PIE - 4.3 Google Drive - armv7 - PIE - 5.0 Google Earth - armv7 - PIE - 4.3 Google+ - armv7 - PIE - 5.0 iBooks - armv7 - PIE - 5.0 IM+ - armv7(s) - PIE - 4.3 Instagram - armv7 - PIE - 4.3 KakaoTalk - armv7(s) - PIE - 4.3 Latitude - armv6|armv7 - NO_PIE - N/A Local - armv6|armv7 - PIE - 4.3 Lync 2010 - armv7 - NO_PIE - 4.3 Messenger - armv7 - PIE - 4.3 MSN World - armv7(s) - PIE - 4.3 SkyDrive - armv6|armv7 - NO_PIE - 4.0 Skype - armv7 - NO_PIE - 4.3 SmartGlass - armv7 - PIE - 5.0 SSH Mobile Free - armv7(s) - PIE - 4.3 SystemTools - armv7(s) - PIE - 4.3 Translate - armv6|armv7 - NO_PIE - N/A Trillian - armv7 - PIE - 4.3 Twitter - armv7 - PIE - 5.0 Usessh - armv7(s) - PIE - 4.3
  • 42. Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 •  iOS 4.3-6.0: PIE main binary randomization • for PIE main executables the main binary and dyld are randomized • main binary and dyld are slid the same amount • randomized by kernel in 256 positions 42 iOS 4.3 - 6.0 - PIE main executable
  • 43. Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 •  iOS 6.1: PIE main binary randomization • since iOS 6.1 the kernel finally generates two separate slides • randomness of both is still limited to 256 positions • knowing addresses in dyld / main no longer leaks address of other 43 iOS 4.3 - 6.0 - PIE main executable iOS 6.1 - PIE main executable
  • 44. Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 •  iOS 4.3-5.1.1: dyld_shared_cache randomization • data and code must slide together (due to codesigning) • hole after code - data usually loaded to 0x3E000000 • max slide determined by difference of end of shared area and end of data • around 4200 different positions 44 iOS 4.3 - 5.1.1 - maximum slide iOS 4.3 - 5.1.1 - no slide
  • 45. Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 •  iOS 6.x: dyld_shared_cache randomization • code and data loaded right next to each other • no more hole - no more wasted space • max slide determined by size of shared area minus size of shared cache • about 21500 different positions for iPod 4G (new devices = more code = less random) 45 iOS 6.x - no slide iOS 6.x - maximum slide
  • 46. Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 •  Part V iOS 6 and the Partial Code-signing Vulnerability 46
  • 47. Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 •  Partial Code-signing Vulnerability (iOS 4) • in iOS 4.x jailbreaks the method of choice to launch untether exploits • when a mach-o is loaded the kernel will load it as is • a possible signature will be registered • missing signature is okay until a not signed executable page is accessed • dyld was tricked with malformed mach-o data structures to execute code 47
  • 48. Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 •  sniffLoadCommands (iOS 4.3.4) • function does pre-handling of mach-o load commands • iOS 4.3.4 adds protection against partial code signing • mach-o load commands must be inside a segment • mach-o load commands can only be in R + X segment • mach-o load commands may not be partially in a segment ➡ effect is that once dyld maps the header R+X it can only continue to work on it if there is a valid signature 48
  • 49. Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 •  Partial Code-signing Vuln (iOS 4.3.4-iOS 5.1.1) • protection in sniffLoadCommands could be bypassed • by having a RW- LC_SEGMENT64 for mach-o header • and a fake R-X LC_SEGMENT for mach-o header • disclosed at CanSecWest 2012 - here on stage • worked because kernel handles LC_SEGMENT64 and dyld did not • magic is that dyld will read mach-o header from from address in memory 49
  • 50. Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 •  sniffLoadCommands (iOS 6.0) • iOS 6.0 adds protection against CSW 2012 trick to sniffLoadCommands • if a LC_SEGMENT64 load command is found an exception is thrown ➡ CSW 2012 trick was already partially broken after iOS 5.1.1 • in iOS 5.1.1 AMFI verified existence of a code signing blob 50
  • 51. Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 •  Load Command Segment Override (iOS 6.0-6.1.2) • bug used by evasi0n • kernel not directly involved in loading dynamic libraries only dyld is • dyld could be tricked with a malicious dylib • contains real R-X segment with load commands in it • contains second R-- segment that contains copy of load commands • virtual address of both segments is set to same position • later segment in mach-o will replace previous in memory • when dyld accesses header it is in RO memory = no sig needed = bypass 51
  • 52. Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 •  sniffLoadCommands (iOS 6.1.3 beta 2) • iOS 6.1.3 beta 2 adds additional protections to sniffLoadCommands • load commands must now be in one segment only • for dynamic libraries a second sniff pass is added • all segments must not intersect the R-X segment containing the load commands ➡ evasi0n untether killed 52
  • 53. Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 •  Part VI iOS 6.1 and Launch-Daemon-Code-Signing 53
  • 54. Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 •  Launch Daemons to launch Untethers • in iOS 5.x jailbreaks were launched on boot via launch daemons • launch daemons are plists describing system services 54 <?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>Label</key> <string>jb</string> <key>ProgramArguments</key> <array> <string>/usr/sbin/corona</string> <string>-f</string> <string>racoon-exploit.conf</string> </array> <key>WorkingDirectory</key> <string>/usr/share/corona/</string> <key>RunAtLoad</key> <true/> <key>LaunchOnlyOnce</key> <true/> <key>DisableAslr</key> <true/> </dict> </plist> DisableAslr was removed from iOS 5.1
  • 55. Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 •  Launch-Daemon-Code-Signing (I) 55 • abuse of launch daemons lead to new iOS 6.1 security feature • launch daemon loading is now code signed • implemented in /bin/launchctl • can be bypassed by setting kernel boot arguments (not possible without low-level exploit)
  • 56. Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 •  Launch-Daemon-Code-Signing (II) 56 • without launch-daemon-code-signing /bin/launchctl scans /System/Library/LaunchDaemons for defined launch daemons and loads them • with activated launch-daemon-code-signing a big plist with all defined launch daemons is loaded instead • launch daemon can only be loaded if it is defined in the plist and exists on disk
  • 57. Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 •  Launch-Daemon-Code-Signing (III) 57 • big launch daemon plist is loaded from /System/Library/Caches/com.apple.xpcd/xpcd_cache.dylib • this dynamic library is within the dyld_shared_cache and therefore code signed • symbol __xpcd_cache must exist • but binary plist is take from sectiondata of __TEXT::__xpcd_cache
  • 58. Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 •  XPCD_CACHE.PLIST 58
  • 59. Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 •  Launch-Daemon-Code-Signing Security 59 How secure Apple wanted Launch-Daemon-Code-Signing to be...
  • 60. Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 •  Launch-Daemon-Code-Signing Security 60 How secure Launch-Daemon-Code-Signing is right now...
  • 61. Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 •  Launch-Daemon-Code-Signing Security • code signing itself seems to stop loading arbitrary launch daemons • but Apple forgot / or ignored /etc/launchd.conf • /etc/launchd.conf defines commands launchctl executes on start • attacker can execute arbitrary existing commands 61 bsexec .. /sbin/mount -u -o rw,suid,dev / setenv DYLD_INSERT_LIBRARIES /private/var/evasi0n/amfi.dylib load /System/Library/LaunchDaemons/com.apple.MobileFileIntegrity.plist bsexec .. /private/var/evasi0n/evasi0n unsetenv DYLD_INSERT_LIBRARIES bsexec .. /bin/rm -f /private/var/evasi0n/sock bsexec .. /bin/ln -f /var/tmp/launchd/sock /private/var/evasi0n/sock
  • 62. Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 •  FAQ: Why not put old launchctl binary on device? Q: “If only the newest iOS 6.1 launchctl binary implements this code signing. Why not put an iOS 6.0 launchctl binary on the device to bypass this protection?“ A: “System binaries like launchctl do not come with a valid code signing signature from Apple. Instead they come only with the table of memory page hashes and entitlements. When the kernel loads such a binary it hashes these tables and checks if the hash is in a whitelist inside the kernel (a.k.a. trust cache). The old launchctl binary will not be accepted because it is not in the trust cache of the new kernel.“ 62
  • 63. Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 •  Final Words • with iOS 6 Apple has tried to kill all public techniques • finally kills some stuff that was previously known and ignored for 10 years • the new mitigations make exploitation a lot harder • when launch daemon code signing is hardened a bit more, persisting on iDevices will become incredibly hard • however there are still weaknesses in most of the protections • ... and tons of kernel information leaks 63
  • 64. Stefan Esser • iOS 6 - Exploitation 280 Days Later • March 2013 •  Questions ? 64