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CNIT 128
Hacking Mobile Devices
3. Attacking iOS Apps

Part 1
Topics: Part 1
• Introduction to Transport Security

• Identifying Insecure Storage

• Patching iOS Applications with Hopper
Topics: Part 2
• Attacking the iOS Runtime

• Understanding Interprocess Communication

• Attacking Using Injection
Attack Scenarios
• From the network

• Tainted data from server-side applications

• Physical access to the phone

• Interactive access to the phone

• Control of another app on the phone
Introduction to Transport
Security
Cleartext Channels
• Such as HTTP

• Never safe

• Even if not transmitting sensitive data like
passwords

• Because an attacker could inject JavaScript
Finding Cleartext
• Examine traffic with Wireshark or Burp
Three SSL/TLS
Implementations
• The URL loading system

• The Carbon Framework

• The Secure Transport API
The URL Loading System
• High-level classes and methods like

• NSURLConnection
• NSURLSession
• Simplest method 

• Most widely adopted
Carbon Framework
• More granular API than the URL loading
system

• Gives developers greater control over
network requests

• Implemented using the CFNetwork class
Secure Transport API
• Low-level API

• The foundation of CFNetwork and the
URL loading system

• Greatest control over the transport

• Complex to implement

• Rarely used directly
Certificate Validation
• SSL and TLS use certificate-based
authentication to

• Ensure that you are communicating with
the desired server

• Prevent eavesdropping and tampering
attacks

• Unless the validation is weakened
Trusted CA
• Certificates must be signed by a trusted
Certificate Authority (CA)

• Accepting self-signed or unvalidated
certificates undermines TLS and SSL

• Allowing MiTM attacks
NSURLConnection Class
• Developer can allow self-signed certificates

• By customizing the
didReceiveAuthenticationChallenge
method
Carbon Framework
• Can allow self-signed certficates by setting up
an SSL settings dictionary

• That sets the
kCFStreamSSLValidatesCertificateChain
constant to false
Secure Transport API
• Setting the
kSSLSessionOptionBreakOnServerAuth
option

• Disables the API's certificate validation

• But the app might have its own trust
evaluation routines, like certificate pinning
Certificate Problems
• Self-signed certificates

• Expired certificates

• Mismatched hostnames

• Expired root CA certificates

• Allowing any root certificate
Dynamic Testing
• Route traffic through the Burp proxy

• Browser detects the SSL error
GOTO Fail
CNIT 128 3. Attacking iOS Applications (Part 1)
CNIT 128 3. Attacking iOS Applications (Part 1)
SSL Session Security
• There are other possible SSL errors if an
app is using the Carbon framework or the
Secure Transport API

• But not if it uses the high-level URL loading
API

• Because there is no way to modify the
SSL/TLS session properties
Protocol Versions
• CFNetwork and Secure Transport APIs

• Both allow a developer to modify the
protocol version

• SSLv2 and SSLv3 are vulnerable
CFNetwork API (Carbon
Framework) Protocol Settings
• These settings specify vulnerable versions

• kCFStreamSocketSecurityLevelSSLv2
• kCFStreamSocketSecurityLevelSSLv3
• kCFStreamSocketSecurityLevelTLSv1
• These settings allow negotiation of insecure
versions

• kCFStreamSocketSecurityLevelNone
• kCFStreamSocketSecurityLevelNegotiatedSSL
Secure Transport API
Protocol Settings
• These settings allow vulnerable versions

• kSSLProtocolUnknown
• kSSLProtocol3
• kTLSProtocol1
• kTLSProtocol11
• kDTLSProtocol1
• This is the preferred setting

• kTLSProtocol12
Cipher Suite Negotiation
Specific Cipher Suite
• Developer may specify an insecure suite

• Secure Transport and CFNetwork APIs allow this
Intercepting Encrypted
Communications
• Necessary to test
apps

• Must install the Burp
certificate on the
phone
Bypassing Certificate
Pinning
• An app has information about the correct
certificate embedded in it

• And refuses to connect with other
certificates

• This must be bypassed to view the network
traffic
Substrate Tweaks
Identifying Insecure
Storage
Local Storage
• An attacker can steal local data when

• The phone is stolen while unlocked

• The Touch ID sensor is bypassed

• Remote compromise through exploitation

• Default credentials on jailbroken phones

• There is no passcode

• Pairing with a malicious computer

• Exploiting the boot chain
Storage Errors
• Stored by app in plaintext

• Using custom encryption with insecure key

• Stored with wrong data protection class
• Inadvertently stored by iOS
Data Protection API
Protection Classes
• No Protection
• Not encrypted

• Unsuitable for sensitive data

• Complete Until First User Authentication
• Discouraged for sensitive data
Identifying Data Protection
Classes
• If data can be backed up

• Back up, then use
Keychain Items
• keychain_dump creates plist files

• protection_class key inside them
Dynamic Analysis
• Tests stored data that doesn't get backed
up

• Use Cydia Substrate

• The old Snoop-It tool was helpful, but it's
gone
Patching iOS
Applications with Hopper
Get the Binary
• Project M 702
Disassemble with Hopper
Jailbreak Detection
Pseudo Code
CNIT 128 3. Attacking iOS Applications (Part 1)

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