iOS Penetration
Testing
A Definitive Guide to iOS Security
—
First Edition
—
Kunal Relan
iOS Penetration Testing A Definitive Guide to iOS Security First Edition Kunal Relan
iOS Penetration Testing: A Definitive Guide to iOS SecurityKunal Relan Noida, Uttar Pradesh India ISBN-13 (pbk): 978-1-4842-2354-3 ISBN-13 (electronic): 978-1-4842-2355-0DOI 10.1007/978-1-4842-2355-0 Library of Congress Control Number: 2016960329Copyright © 2016 by Kunal RelanThis work is subject to copyright. All rights are reserved by the Publisher, whether the whole or part of the material is concerned, specifically the rights of translation, reprinting, reuse of illustrations, recitation, broadcasting, reproduction on microfilms or in any other physical way, and transmission or information storage and retrieval, electronic adaptation, computer software, or by similar or dissimilar methodology now known or hereafter developed.Trademarked names, logos, and images may appear in this book. Rather than use a trademark symbol with every occurrence of a trademarked name, logo, or image we use the names, logos, and images only in an editorial fashion and to the benefit of the trademark owner, with no intention of infringement of the trademark.The use in this publication of trade names, trademarks, service marks, and similar terms, even if they are not identified as such, is not to be taken as an expression of opinion as to whether or not they are subject to proprietary rights.While the advice and information in this book are believed to be true and accurate at the date of publication, neither the authors nor the editors nor the publisher can accept any legal responsibility for any errors or omissions that may be made. The publisher makes no warranty, express or implied, with respect to the material contained herein.Managing Director: Welmoed SpahrLead Editor: Nikhil KarkalTechnical Reviewer: Nishant Das PatnaikEditorial Board: Steve Anglin, Pramila Balan, Laura Berendson, Aaron Black, Louise Corrigan, Jonathan Gennick, Robert Hutchinson, Celestin Suresh John, Nikhil Karkal, James Markham, Susan McDermott, Matthew Moodie, Natalie Pao, Gwenan SpearingCoordinating Editor: Prachi MehtaCopy Editor: Kezia EndsleyCompositor: SPi GlobalIndexer: SPi GlobalArtist: SPi GlobalDistributed to the book trade worldwide by Springer Science+Business Media New York, 233 Spring Street, 6th Floor, New York, NY 10013. Phone 1-800-SPRINGER, fax (201) 348-4505, e-mail orders-ny@springer-sbm.com , or visit www.springeronline.com . Apress Media, LLC is a California LLC and the sole member (owner) is Springer Science + Business Media Finance Inc (SSBM Finance Inc). SSBM Finance Inc is a Delaware corporation. For information on translations, please e-mail rights@apress.com , or visit www.apress.com . Apress and friends of ED books may be purchased in bulk for academic, corporate, or promotional use. eBook versions and licenses are also available for most titles. For more information, reference our Special Bulk Sales–eBook Licensing web page at www.apress.com/bulk-sales . Any source code or other supplementary materials referenced by the author in this text are available to readers at www.apress.com . For detailed information about how to locate your book’s source code, go to www.apress.com/source-code/ . Readers can also access source code at SpringerLink in the Supplementary Material section for each chapter. Printed on acid-free paper
Th is book is dedicated to my mom, my spiritual guru for inspiring me to live, my mentor who always supported me in this journey, and to all the weirdoes like me; I love you all.
vContents at a GlanceAbout the Author ............................................................................xiiiAbout the Technical Reviewer .........................................................xvAcknowledgments .........................................................................xviiIntroduction ....................................................................................xix ■Chapter 1: Introduction to iOS ........................................................1 ■Chapter 2: iOS App Development Basics ......................................13 ■Chapter 3: iOS App Vulnerabilities and Jailbreaking ....................31 ■Chapter 4: Blackbox Testing iOS Apps ..........................................47 ■Chapter 5: iOS Security Toolkit .....................................................73 ■Chapter 6: Automating App Testing ..............................................97 ■Chapter 7: iOS App Security Practices .......................................119Index ..............................................................................................131
viiContentsAbout the Author ............................................................................xiiiAbout the Technical Reviewer .........................................................xvAcknowledgments .........................................................................xviiIntroduction ....................................................................................xix ■Chapter 1: Introduction to iOS ........................................................1 iOS Introduction .......................................................................................1 Security History .......................................................................................................2 Code Signing ............................................................................................................2 Data Execution Prevention (DEP) ..............................................................................3 Address Space Layout Randomization (ASLR) ..........................................................3 Sandbox ....................................................................................................................3 iOS Boot Procedure ...................................................................................................4 Updates.....................................................................................................................5 What’s New? .............................................................................................................6 System Insight ..........................................................................................................7 iOS System Hierarchy ..............................................................................8 Applications ..............................................................................................................9 Library ......................................................................................................................9 Bin Folder ...............................................................................................................10 Dev Directory ..........................................................................................................10 Lib Folder ................................................................................................................10 Sbin Directory .........................................................................................................10
■ CONTENTSviii Tmp Directory .........................................................................................................10 Developer Directory ................................................................................................10 System Directory ....................................................................................................10 Boot Directory .........................................................................................................11 Etc Directory ...........................................................................................................11 mnt Directory ..........................................................................................................11 usr Directory ...........................................................................................................11 var Directory ...........................................................................................................11 User Directory .........................................................................................................11 Private Directory .....................................................................................................11 iOS Application Overview ......................................................................11 Summary ...............................................................................................12 ■Chapter 2: iOS App Development Basics ......................................13 Introduction to Objective-C and Swift ...................................................13 Objective-C Runtime ...............................................................................................13 Basic Terminology in Objective-C ...........................................................................14 Object Creation .......................................................................................................15 Data Types ..............................................................................................................15 Methods ................................................................................................16 Instance Methods ...................................................................................................16 Class Methods ........................................................................................................17 Introduction to Swift ..............................................................................17 Swift Runtime .........................................................................................................18 Compatibility with Objective-C ...............................................................................18 Stored Properties ....................................................................................................18 Classes and Methods..............................................................................................19 Structures ...............................................................................................................20
■ CONTENTSix Introduction to Xcode ............................................................................20 Getting Started with Xcode .....................................................................................21 Cocoa Framework .................................................................................22 CocoaPods .............................................................................................22 Hello World with Swift ...........................................................................23 iOS Application Architecture ..................................................................29 Summary ...............................................................................................30 ■Chapter 3: iOS App Vulnerabilities and Jailbreaking ....................31 Introduction to Security and Vulnerabilities in iOS ................................31 What Is Jailbreaking? .............................................................................................31 Jailbreaking iOS .....................................................................................................32 SSHing in iOS ..........................................................................................................34 Installing the Tools .................................................................................35 Installing class-dump .............................................................................................35 Installing the libimobiledevice Library ....................................................................36 Installing Cycript .....................................................................................................37 Setting Up a Proxy ..................................................................................................38 Installing Keychain Dumper ....................................................................................38 Common iOS Vulnerabilities ..................................................................40 Buffer Overfl ows .....................................................................................................40 Invalidated Input .....................................................................................................41 Privilege Escalation ................................................................................................43 Insecure Data Storage ............................................................................................43 Insecure Transport Layer ........................................................................................43 Client-Side Injection ...............................................................................................44 Weakness in Authentication and Authorization .....................................................45 Summary ...............................................................................................45