This document discusses security issues and vulnerabilities in the iOS operating system. It begins with an overview of the iOS hardware and software architecture, including the security features like sandboxing and code signing. It then explains what a jailbreak is and how it attacks the chain of trust to bypass these protections. The document outlines several ways sensitive data can be accessed, such as through property lists, SQLite databases, keychains, logs, and cached files. It also discusses client-side vulnerabilities like SQL injection, XSS, and logging of sensitive information. Finally, it promotes learning about mobile security through tools like OWASP iGoat and the speaker's company AppKnox.

1. iOS (Vulner)ability
Subho Halder
Co Founder
AppKnox

3. ./WhoAmI
Co Founder of AppKnox ( XYSec Labs )
Python Lover
Sole Creator and Developer of Android Framework for Exploitation (AFE)
Found Security Bugs in Apple, Google, Skype, Webkit, Facebook, Microsoft, …..

4. Security is ……
http://xkcd.com/327/

5. NSLog [@“Agenda”];
Quick overview of iPhone iOS Platform.
iOS Security Structure
What is a Jailbreak?
iOS App (IN)Securities

6. Peek into a state-of-art Prison

7. iOS Hardware Architecture
Application Processor
Baseband
iOS
User interaction
Applications
...
NucleusOS
Radio communication

8. iOS Hardware
Architecture
Application Processor Baseband Processor
audio
display
power managment
camera
WIFI
BT
GSM
UART
I2S
GPIO
DMA
controls
sim/net-lock !

9. Phew, Security Architecture

10. ***[Sandboxing]***
NAND Flash
FTL: converts logical partition to NAND flash architecture
looks like BLOCK device
System Partition / (Read Only)
User Partition /private/var
NAND
FTL
Block Device
/ (RO)
(System Partition)
/private/var (RW)
(User Partition)

11. ***[Sandboxing]***
3rd Party lives only on User Partition
Apps run as mobile user
Kernel Signature checks executables
in system-call execve()
%{ How did you Jailbreak it? }%
NAND
FTL
Block Device
/ (RO)
(System Partition)
/private/var (RW)
(User Partition)

12. **Memory Protection
W^X Policy
Non Executable Stack or Heap
ASLR (Address Space Layout Randomisation)
%{ Did you forget about Return-Oriented-Program }%

13. Code Signing
Implemented inside Kernel
Kernel signature checks executables in systemcall execve()
Kernel stored on System Partition (kernelcache)
Kernel is signature checked before being loaded.
%{ Can still be by-passed :/ }%

14. Encryption @#%$#^% !
Everythong is encrypted
Hardware AES Engine
Keys derived from hardware keys GID-key UID-key
%{Possible to use Jailbreak tools e.g. Syringe to use the hardware engine}%

15. What is J@!lbr3@k ?

16. How your iPhone boots up?
signature
check
signature
check
signature
check
signature
check
Bootrom LLB
(Low Level Bootloader)
iBoot Kernel Application
NOR NOR NAND NAND

17. Recovery Mode?
Bootrom
LLB
(Low Level
Bootloader)
iBoot
signature
check
signature
check
Kernel
Kernel
Ramdisk

18. DFU Mode !
Bootrom iBSS iBEC Kernel
Ramdisk
Bootrom LLB
(Low Level Bootloader)
iBoot Kernel Application
minimal
iBoot

19. Attacking the chain of trust!
signature
check
Bootrom
LLB
(Low Level
Bootloader)
iBoot Kernel Application
signature
check
signature
check
signature
check
signature
check
attack here
(cannot be fixed)
attack here
attack here
attack here
System
Software

20. Where do we go wrong?

21. Plists
Used by iPhone to store saved properties and data
XML
Binary (compressed XML) (depreciated)
The binary plists need converting, you can use:
plutil to convert to XML
Property List Editor (in XCode)
plists contain all kinds of juicy information. Check for:
Cookies, emails, usernames, passwords, sensitive application data, client side role identifiers, protocol handlers,
etc.

22. B00M! :O

23. INSERT into `SQLite`
A lot of iOS applications sensitive data in SQLite3 databases on the device.
Sqlite3 does not have built-in support for encryption.
There are extensions (CEROD is one, sqlcipher is another) that support encryption, but
the code is not publicly available, you need to license it. Apple has not, so the included
version of sqlite3 does not support encrypted databases.
Still dangerous to store stuff client side.
To bypass: Cerod is as simple as looking for “cerod:passwd” or break pointing and
pulling out of memory: sqlite3_open(":cerod:passwd:filename.db", &db);

24. )()()( Keychains )()()(
Keychain = Encrypted container for storing sensitive information
Smarter devs store passwords and sensitive data using the keychain.
Unfortunately with access to a phone and jailbreaking we can decrypt the
keychain and dump the contents.

25. tail -f /var/logs/
iOS Logs lots of data, NSLog especially, They can be viewed after the fact in:
~/Library/Logs/CrashReporter/MobileDevice/<Device name>/private/var/
log/system.log
Can be viewed in you mac “console” app under utilities

26. File Caching m/m/
If the application uses PDF, Excel, or other files it may be possible that these
files may have been cached on the device.
These can be found at: ~/Library/Application Support/iPhone simulator/x.x.x/
Applications/<application folder>/Documents/temp.pdf

27. $(`Keyboard Caching`)
Keystrokes for predictive spellcheck are stored in:
~/Library/Application Support/iPhone Simulator/x.x.x/Library/Keyboard/
dynamic-text.dat
This issue is similar to autocomplete for web browsers.
Already disabled for password fields Should be disabled for any potentially sensitive
fields (account numbers, SSN, etc, etc…)
Set UITextField property autocorrectionType = UITextAutocorrectionNo for mitigation.

28. Snapshot Caching
When in an application and the home button is pushed, the application stores a
snapshot (screenshot) in the apps snapshot folder
~/Library/Application Support/iPhone Simulator/x.x.x/Applications/
<application folder>/Library/Caches/Snapshots/
These persist until reboot. Hopefully you weren’t on a screen with any sensitive
data!

29. Snapshot Caching

30. SQL Injection Client-Side
SQL injection is a problem on the client side too!
BAD:
NSString *sql = [NSString stringWithFormat:@"SELECT name FROM products
WHERE id = '%@'", id]; const char *query = [sql UTF8String];
GOOD:
const char *sql = "SELECT name FROM products WHERE id = ?";
sqlite3_prepare_v2(database, sql, -1, &sql_statement, NULL);
sqlite3_bind_text(&sql_statement, 1, id, -1, SQLITE_TRANSIENT);

31. XSS Client-Side
Can occur whenever user controlled Objective C variables populated in to
WebView
stringByEvaluatingJavaScriptFromString
NSString *javascript = [[NSString alloc] initWithFormat:@"var myvar="%@";",
username];
[mywebView stringByEvaluatingJavaScriptFromString:javascript];

32. Vulnerable Obj-C Methods
NSLog()
[NSString stringWithFormat:]
[NSString initWithFormat:]
[NSMutableString appendFormat:]
[NSAlert informativeTextWithFormat:]
[NSPredicate predicateWithFormat:]
[NSException format:]
NSRunAlertPanel

33. How can you get started?
https://www.owasp.org/index.php/OWASP_iGoat_Project

34. AppKnox - Cloud Based
Security Automation Tool

35. Available for Android
Coming soon for iOS

36. –Cicero
“There is no castle so strong that it cannot be
overthrown”

37. Thank You
https://www.appknox.com
http://subho.me
@sunnyrockzzs
subho.halder@gmail.com