Hacking (and Defending) iPhone Applications Kevin Stadmeyer Garrett Held COPYRIGHT TRUSTWAVE 2011 CONFIDENTIAL Who Are We? Garrett Held and Kevin Stadmeyer ›Managing Consultants with Trustwave SpiderLabs ›Have performed.

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Transcript Hacking (and Defending) iPhone Applications Kevin Stadmeyer Garrett Held COPYRIGHT TRUSTWAVE 2011 CONFIDENTIAL Who Are We? Garrett Held and Kevin Stadmeyer ›Managing Consultants with Trustwave SpiderLabs ›Have performed.

Hacking (and Defending) iPhone
Applications
Kevin Stadmeyer
Garrett Held
COPYRIGHT TRUSTWAVE 2011
CONFIDENTIAL
Who Are We?
Garrett Held and Kevin Stadmeyer
›Managing Consultants with Trustwave SpiderLabs
›Have performed hundreds of application tests from
mainframe to web to mobile
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Agenda
What we’ll cover –
secure coding and beyond, what to look
for when assessing an iPhone application
›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
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The Basics
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Just the Facts, Ma’am
Why are people attacking mobile apps?
›Stealing Money
›Embarrassing People (“Hactivists”)
›Get Famous
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Just the Facts, Ma’am
iPhone Apps in the Press
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Just the Facts, Ma’am
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?
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Just the Facts, Ma’am
What Security Model We’re Not Talking About?
›Layer 1: Apple Store
›Layer 2: Sandboxing via “Seatbelt”
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Just the Facts, Ma’am
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Setting Up The Testing Environment
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Setting Up The Testing Environment
Don’t you mean setting up the decompiler?
›No
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We Built This City
On das metal – Step 1: get your proxy right
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We Built This City
On das metal –
Step 2: Get ya certs heard!
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We Built This City
On das metal –
Step 3: Roll It Up
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We Built This City
On das metal –
Step 4: Mail it!
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We Built This City
On das metal –
Step 5: Install It
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We Built This City
On das metal –
Step 6: Install It (Errrr….)
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We Built This City
On das metal –
Step 7: Proxy It!
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We Built This City
On das metal – Step 8: Victory!
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We Built This City
On The Computer Machine – Step 6: Install It!
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We Built This City
On The Computer Machine – Step 7: Install It!
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We Built This City
On The Computer Machine
›The format is X’<SHA1 Fingerprint>’
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We Built This City
Now What?
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We Built This City
Now What?
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We Built This City
Now What?
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Secure Storage Of Data
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Storing Credentials
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
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Storing Credentials
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
[1] http://www.sit.fraunhofer.de/en/Images/sc_iPhone%20Passwords_tcm502-80443.pdf
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Storing Credentials
Where Should You Store Them?
›Not on the device?
– At least not in plaintext!
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Storing Credentials
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!
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Storing Credentials
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
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Storing Credentials
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
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Storing Credentials
B-b-b-but kSecAttrAccessibleWhenUnlocked!
›By default iOS writes information to the keychain with
this attribute
›By default most user’s passwords suck
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Storing Credentials
Look Familiar?
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Storing Credentials
Most Users
Pick Simple PINS
10,000 possibilities
~.1 second to crack (100k a second is pretty standard)
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Storing Credentials
Protect Stupid Users
 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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I Accidently Your Data…
Screenshots
›Where are they stored?
›When are they taken?
›Who can access them!
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I Accidently Your Data…
Screenshots
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I Accidently Your Data…
Screenshot Protection
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I Accidently Your Data…
Other Storage Of
Information
›Autocomplete, etc.
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I Accidently Your Data…
Autocomplete
›Override autocomplete
›textfield.autocorrectionType =
UITextAutocorrectionNone
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Client Side Sanitization
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Client Side? More like Bad side, amirite?
It’s bad…
›Less burden on server
›Critical bypasses (yay!)
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Client Side? More like Bad side, amirite?
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
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Client Side? More like Bad side, amirite?
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
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Client Side? More like Bad side, amirite?
How To Do It Right
›Server Side Controls
›Assume everything coming in came from a rouge or
compromised client
›Enforce secure communications
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Client Side? More like Bad side, amirite?
What Applies in the iOS world?
Applies
Does Not Apply
SQL Injection
CSRF*
XML Injection
XSS*
Other Injection
Privilege Escalation
Session Hijacking
Overflows (Buffer, Integer)
Format String Problems
Insecure use of SSL
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Client Side? More like Bad side, amirite?
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
]1] http://www.crn.com.au/News/265931,video-details-android-browser-intercept-flaw.aspx
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Client Side? More like Bad side, amirite?
Break That Down Into Attackers View
Attacker Targets Server
Attacker Targets Device
SQL Injection
Overflows (Buffer, Integer)
XML Injection
Format String Problems
Other Injection
Privilege Escalation
Session Hijacking
Insecure use of SSL
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Client Side? More like Bad side, amirite?
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
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Client Side? More like Bad side, amirite?
Shifting Paradigms
– we hate ourselves
›Local Storage Review
– What is stored and why?
›Educating QA
– Proxy testing
›Review Local and Remote Inputs
›Information Leakage
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A New Methodology
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
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A New Methodology
Educating QA
›Develop test cases for new and old vulnerabilities
›Formal process for testing communications and
settings
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A New Methodology
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.
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A New Methodology
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.
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Secure Coding
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Buffer Overflow
What Can Go Wrong?
›Arbitrary executable code could be loaded and
executed on the device
›Bypass “seatbelt”
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Buffer Overflow
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
[1] http://developer.apple.com/library/mac/#documentation/Security/Conceptual/SecureCodingGuide/Articles/BufferOverflows.html
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Format String Attack
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”
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Format String Attack
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
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Race Conditions
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.
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Race Conditions
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.
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Race Conditions
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.
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Server Side
What Can Go Wrong?
›Just about everything
–
–
–
–
Logic vulnerabilities
Weak session controls
Classic web application vulnerabilities
Too much trust in the client-side controls
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Server Side
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
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Push Notifications
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Push Notifications
Real Fast
http://www.dhanjani.com/
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Secure Communications
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Secure Communications
SSL Whaaaa?
›NSURL method
– iOS is secure by default in regards to SSL
certs when using this method to retrieve
HTTPS content
Source: http://www.flickr.com/photos/mikebaird/
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Secure Communications
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.”
[1] TWSL2011-007: iOS SSL Implementation Does Not Validate Certificate Chain,
https://www.trustwave.com/spiderlabs/advisories/TWSL2011-007.txt
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Secure Communications
SSL Whaaaa?
Source: http://www.flickr.com/photos/lenore-m/
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This Is It
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This Is It
Review
›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
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This Is It
Summary
›Testing is easy
– For you and for “them”
›Security is hard
– Really just for you
›So test everything!
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