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Kevin StadmeyerGarrett Held

COPYRIGHT TRUSTWAVE 2011 CONFIDENTIAL

Hacking (and Defending) iPhone Applications

COPYRIGHT TRUSTWAVE 2011 CONFIDENTIAL

Garrett Held and Kevin Stadmeyer

› Managing Consultants with Trustwave SpiderLabs› Have performed hundreds of application tests from mainframe to web to mobile

Who Are We?

COPYRIGHT TRUSTWAVE 2011 CONFIDENTIAL

› The Basics› Setup For Testing› Secure Storage of Data And Credentials› Inadvertent Local Storage and Caching› Client Side Sanitization› Secure Coding› Push Notifications› Secure Communications

Agenda

What we’ll cover – secure coding and beyond, what to look for when assessing an iPhone application

COPYRIGHT TRUSTWAVE 2011 CONFIDENTIAL

The Basics

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Why are people attacking mobile apps?

› Stealing Money› Embarrassing People (“Hactivists”)› Get Famous

Just the Facts, Ma’am

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Just the Facts, Ma’am

iPhone Apps in the Press

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How are people attacking mobile apps?

› New and unsafe operating systems?› Terrible developers who don’t care?› Clueless users who don’t know they should care?

Just the Facts, Ma’am

COPYRIGHT TRUSTWAVE 2011 CONFIDENTIAL

What Security Model We’re Not Talking About?

› Layer 1: Apple Store› Layer 2: Sandboxing via “Seatbelt”

Just the Facts, Ma’am

COPYRIGHT TRUSTWAVE 2011 CONFIDENTIAL

Just the Facts, Ma’am

COPYRIGHT TRUSTWAVE 2011 CONFIDENTIAL

Setting Up The Testing Environment

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Don’t you mean setting up the decompiler?

› No

Setting Up The Testing Environment

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On das metal – Step 1: get your proxy right

We Built This City

COPYRIGHT TRUSTWAVE 2011 CONFIDENTIAL

On das metal – Step 2: Get ya certs heard!

We Built This City

COPYRIGHT TRUSTWAVE 2011 CONFIDENTIAL

On das metal – Step 3: Roll It Up

We Built This City

COPYRIGHT TRUSTWAVE 2011 CONFIDENTIAL

On das metal – Step 4: Mail it!

We Built This City

COPYRIGHT TRUSTWAVE 2011 CONFIDENTIAL

On das metal – Step 5: Install It

We Built This City

COPYRIGHT TRUSTWAVE 2011 CONFIDENTIAL

On das metal – Step 6: Install It (Errrr….)

We Built This City

COPYRIGHT TRUSTWAVE 2011 CONFIDENTIAL

On das metal – Step 7: Proxy It!

We Built This City

COPYRIGHT TRUSTWAVE 2011 CONFIDENTIAL

On das metal – Step 8: Victory!

We Built This City

COPYRIGHT TRUSTWAVE 2011 CONFIDENTIAL

On The Computer Machine – Step 6: Install It!

We Built This City

COPYRIGHT TRUSTWAVE 2011 CONFIDENTIAL

On The Computer Machine – Step 7: Install It!

We Built This City

COPYRIGHT TRUSTWAVE 2011 CONFIDENTIAL

On The Computer Machine

We Built This City

› The format is X’<SHA1 Fingerprint>’

COPYRIGHT TRUSTWAVE 2011 CONFIDENTIAL

Now What?

We Built This City

COPYRIGHT TRUSTWAVE 2011 CONFIDENTIAL

Now What?

We Built This City

COPYRIGHT TRUSTWAVE 2011 CONFIDENTIAL

Now What?

We Built This City

COPYRIGHT TRUSTWAVE 2011 CONFIDENTIAL

Secure Storage Of Data

COPYRIGHT TRUSTWAVE 2011 CONFIDENTIAL

The Keychain

› Indefinite Storage› Can you store credentials securely without the keychain?– Don’t let the feature make you lazy– Don’t store credentials in the keychain unless you don’t

care about certain things

Storing Credentials

COPYRIGHT TRUSTWAVE 2011 CONFIDENTIAL

Keychain Compromise via Jailbreaking

› Through a series of steps, retrieves passwords stored in the keychain [1]

› Researchers compromised keychain passwords only, not other protected classes such as passwords for websites– Jailbreak stolen iPhone (requires physical access), gain

SSH access– Copy scripts that will compromise the keychain– Scripts output the victims passwords

Storing Credentials

[1] http://www.sit.fraunhofer.de/en/Images/sc_iPhone%20Passwords_tcm502-80443.pdf

COPYRIGHT TRUSTWAVE 2011 CONFIDENTIAL

Where Should You Store Them?

› Not on the device?– At least not in plaintext!

Storing Credentials

COPYRIGHT TRUSTWAVE 2011 CONFIDENTIAL

Securely Storing Data At Rest – things to look for

› Database calls?– Injection Possible?

› Using Core Data?– Does the application trust the integrity of the data?– Remember trust boundaries!

Storing Credentials

COPYRIGHT TRUSTWAVE 2011 CONFIDENTIAL

Recommendations for non-credential data

› Do not store data on the phone if at all possible– Never has it been so easy to lose so much data so fast!

› Require user to enter a passcode– Can still be brute-forced with time once the encrypted

text is found– Poor user-experience on mobile devices

Storing Credentials

COPYRIGHT TRUSTWAVE 2011 CONFIDENTIAL

Recommendations for non-credential data

› Store decryption key on a server and require credentials (non-stored) to access key– Only works for applications that do not require offline

access– Increases data usage– Revocable though– Data not “stored” in the cloud

Storing Credentials

COPYRIGHT TRUSTWAVE 2011 CONFIDENTIAL

B-b-b-but kSecAttrAccessibleWhenUnlocked!

› By default iOS writes information to the keychain with this attribute

› By default most user’s passwords suck

Storing Credentials

COPYRIGHT TRUSTWAVE 2011 CONFIDENTIAL

Look Familiar?

Storing Credentials

COPYRIGHT TRUSTWAVE 2011 CONFIDENTIAL

Most Users

Storing Credentials

Pick Simple PINS10,000 possibilities~.1 second to crack (100k a second is pretty standard)

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Protect Stupid Users

Storing Credentials

Require Strong Passwords (8+ alpha-numeric chars)

Use REAL and GOOD encryption Don’t rely on an inherently

insecure PIN to protect users. If they knew what they were

doing we wouldn’t be here today.

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Inadvertent Local Storage and Caching

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Screenshots

› Where are they stored?› When are they taken?› Who can access them!

I Accidently Your Data…

COPYRIGHT TRUSTWAVE 2011 CONFIDENTIAL

Screenshots

I Accidently Your Data…

COPYRIGHT TRUSTWAVE 2011 CONFIDENTIAL

Screenshot Protection

I Accidently Your Data…

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Other Storage Of Information

› Autocomplete, etc.

I Accidently Your Data…

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Autocomplete

› Override autocomplete› textfield.autocorrectionType = UITextAutocorrectionNone

I Accidently Your Data…

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Client Side Sanitization

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It’s bad…

› Less burden on server› Critical bypasses (yay!)

Client Side? More like Bad side, amirite?

COPYRIGHT TRUSTWAVE 2011 CONFIDENTIAL

It’s bad…

› Some classic Web Application faults translate well into the iPhone.

› Web developers relied on:– JavaScript controls– Hidden fields– JSON responses– Information stored in Flash objects

Client Side? More like Bad side, amirite?

COPYRIGHT TRUSTWAVE 2011 CONFIDENTIAL

Rogue Clients

› Attackers can write apps (Some testers, too)› Client side secrets can be decompiled– We don’t care if it’s obfuscated for now, that’s a

point in time.

› Distributed through trusted App store?– Already happened to Android

Client Side? More like Bad side, amirite?

COPYRIGHT TRUSTWAVE 2011 CONFIDENTIAL

How To Do It Right

› Server Side Controls› Assume everything coming in came from a rouge or compromised client

› Enforce secure communications

Client Side? More like Bad side, amirite?

COPYRIGHT TRUSTWAVE 2011 CONFIDENTIAL

What Applies in the iOS world?

Client Side? More like Bad side, amirite?

Applies Does Not ApplySQL Injection CSRF*XML Injection XSS*Other InjectionPrivilege EscalationSession HijackingOverflows (Buffer, Integer)Format String Problems Insecure use of SSL

COPYRIGHT TRUSTWAVE 2011 CONFIDENTIAL

CSRF and XSS In Apps?

› Calls to browser– Recent Android Issue [1]– Loads javascript:alert(document.cookie)

› Embedded browser shares web app issues

› Rogue applications and rogue users

Client Side? More like Bad side, amirite?

]1] http://www.crn.com.au/News/265931,video-details-android-browser-intercept-flaw.aspx

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Break That Down Into Attackers View

Client Side? More like Bad side, amirite?

Attacker Targets Server Attacker Targets DeviceSQL Injection Overflows (Buffer, Integer)XML Injection Format String Problems Other InjectionPrivilege EscalationSession HijackingInsecure use of SSL

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What Does This Mean to a Developer?

› Time to throw out any assumptions that the device will protect you by obfuscating anything

› A new set of security practices need to be developed and followed when creating App’s

Client Side? More like Bad side, amirite?

COPYRIGHT TRUSTWAVE 2011 CONFIDENTIAL

Shifting Paradigms – we hate ourselves

› Local Storage Review– What is stored and why?

› Educating QA– Proxy testing

› Review Local and Remote Inputs› Information Leakage

Client Side? More like Bad side, amirite?

COPYRIGHT TRUSTWAVE 2011 CONFIDENTIAL

Local Storage Review

› Review what’s stored on the device by the application

› Review what’s stored on the device by iOS

› Keep it simple, review to remove

A New Methodology

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Educating QA

› Develop test cases for new and old vulnerabilities

› Formal process for testing communications and settings

A New Methodology

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Local And Remote Inputs

› User input from Apps is always a concern

› Don’t forget about responses that could be intercepted or hijacked.

› Maintain the integrity of the device.

A New Methodology

COPYRIGHT TRUSTWAVE 2011 CONFIDENTIAL

Information Leakage

› Examine all traffic to / from the application, like should be done with web applications

› Additional examination of what sensitive data may be in the binary.– Is it necessary? Keep it simple. Review to Remove.

A New Methodology

COPYRIGHT TRUSTWAVE 2011 CONFIDENTIAL

Secure Coding

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What Can Go Wrong?

› Arbitrary executable code could be loaded and executed on the device

› Bypass “seatbelt”

Buffer Overflow

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How To Do It Right

› Same concerns as in C› Use appropriate functions [1]– Example: strlcpy NOT strncpy

› Properly calculate buffer size (constants)› Includes integer bounds checking

Buffer Overflow

[1] http://developer.apple.com/library/mac/#documentation/Security/Conceptual/SecureCodingGuide/Articles/BufferOverflows.html

COPYRIGHT TRUSTWAVE 2011 CONFIDENTIAL

What Can Go Wrong?

› Application displays user input (as applications are known to do)

› Uses the [NSString stringWithFormat] method› Uses the printf function› Attacker sends “%s%s%s%s” instead of “Hello”

Format String Attack

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How To Do It Right

› Enforce Secure Coding Standard– Just like web applications– No vulnerable function should accept untrusted

user input that could be used to determine the format of the output

Format String Attack

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What Can Go Wrong?

› Application manages state using the deviceID NOT the session ID.

› Sessions not terminated properly on the server side

› Following Conditions– User logged into the application at some point in

the last day and subsequently logged out.– Attacker supplies wrong credentials through the

mobile app.

Race Conditions

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What Can Go Wrong?

› Following Conditions– Application request “session refresh” while waiting

for the incorrect login response to be sent. – Server “refreshes” the session based on the device

ID.– Application receives a response indicating the login

was successful, followed by a login denied error. – Application subsequently ignores the login denied,

continues using the previous session now tied to the Device ID.

Race Conditions

COPYRIGHT TRUSTWAVE 2011 CONFIDENTIAL

How To Do It Right

› Strong server side controls over access– Policy enforcement on concurrent logins– Do not maintain session via Device ID– Properly Logout Users

› Make sure any mobile applications have the same, proper logic enforcement as web applications.

Race Conditions

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What Can Go Wrong?

› Just about everything– Logic vulnerabilities– Weak session controls– Classic web application vulnerabilities– Too much trust in the client-side controls

Server Side

COPYRIGHT TRUSTWAVE 2011 CONFIDENTIAL

How To Do It Right

› Harden the server– Every client is treated like it might be malicious

› Use same guidelines as Web Apps– OWASP Secure Development

Server Side

COPYRIGHT TRUSTWAVE 2011 CONFIDENTIAL

Push Notifications

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Real Fast

Push Notifications

http://www.dhanjani.com/

COPYRIGHT TRUSTWAVE 2011 CONFIDENTIAL

Secure Communications

COPYRIGHT TRUSTWAVE 2011 CONFIDENTIAL

SSL Whaaaa?› NSURL method

– iOS is secure by default in regards to SSL certs when using this method to retrieve HTTPS content

Secure Communications

Source: http://www.flickr.com/photos/mikebaird/

COPYRIGHT TRUSTWAVE 2011 CONFIDENTIAL

Well, that’s true now…› SSLizzard

– Exploit developed by SpiderLabs to take advantage of weakness in certificate validation. [1]

– Allowed SSL MITM attacks without errors.– Apple patched this, “This vulnerability has been corrected in versions

5.0b4, 4.3.5, and 4.2.10.”

Secure Communications

[1] TWSL2011-007: iOS SSL Implementation Does Not Validate Certificate Chain, https://www.trustwave.com/spiderlabs/advisories/TWSL2011-007.txt

COPYRIGHT TRUSTWAVE 2011 CONFIDENTIAL

SSL Whaaaa?

Secure Communications

Source: http://www.flickr.com/photos/lenore-m/

COPYRIGHT TRUSTWAVE 2011 CONFIDENTIAL

This Is It

COPYRIGHT TRUSTWAVE 2011 CONFIDENTIAL

› The Basics› Setup For Testing› Secure Storage of Data And Credentials› Inadvertent Local Storage and Caching› Client Side Sanitization› Secure Coding› Push Notifications› Secure Communications

This Is It

Review

COPYRIGHT TRUSTWAVE 2011 CONFIDENTIAL

Summary

› Testing is easy– For you and for “them”

› Security is hard– Really just for you

› So test everything!

This Is It

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