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Please, Please, PLEASE! Defend Your Mobile Apps! 
Jerod Brennen, CISSP 
CTO & Principal Security Consultant, Jacadis 
Strengthening Cybersecurity Defenders #ISC2Congress
2 #ISC2Congress 
Agenda 
» A Little Understanding Goes a Long Way 
» Mobile App Defense 101 
» Attacking Your Own Apps 
» Vetting Apps 
» Resources
How to Write Good Code 
From http://xkcd.com/844/ 
3 #ISC2Congress
Understand Your Environment 
» What development methodologies do we follow? 
» What programming languages do we use? 
» What risk/security frameworks do we follow? 
» What third-party libraries do we use? 
» What stages in the development process require 
approval from the security team? 
4 #ISC2Congress
Understand Your Platforms 
5 #ISC2Congress 
» iOS 
» Android 
» BlackBerry 
» Windows
Three Four Key Security Checks 
6 #ISC2Congress 
» Defined Security 
Requirements 
– Project Plan 
– RFP, Contracts, etc. 
» Source Code Security 
Reviews 
– Manual Reviews 
– Reverse Binaries 
» Security Tests in QA 
• Positive AND Negative 
Test Cases 
» Analysis of “Deployed” 
Apps 
• Automated Scans 
• Manual Analysis
Source Code Reviews (OWASP) 
7 #ISC2Congress 
» Methodology (v1.1, current) 
• Preparation 
• Security Code Review in the SDLC 
• Security Code Review Coverage 
• Application Threat Modeling 
• Code Review Metrics 
» Methodology (v2.0, in development) 
• Preparation 
• Application Threat Modeling 
• Understanding Code Layout/Design/Architecture 
• Reviewing by Technical Control 
• Reviewing by Vulnerability 
• Security Code Review for Agile Development
QA Security Test Cases 
8 #ISC2Congress 
» Positive AND Negative 
» Top 10 Negative Test Cases 
• Embedded Single Quote 
• Required Data Entry 
• Field Type Test 
• Field Size Test 
• Numeric Bounds Test 
• Numeric Limits Test 
• Date Bounds Test 
• Date Validity 
• Web Session Testing 
• Performance Changes 
List from http://www.sqatester.com/methodology/Top10NegativeTestCases.htm
Application Analysis 
» Automated scanning tools and manual analysis 
9 #ISC2Congress 
» OWASP Testing Guide (v3) 
• Information Gathering 
• Configuration Management Testing 
• Authentication Testing 
• Session Management Testing 
• Authorization Testing 
• Business Logic Testing 
• Data Validation Testing 
• Testing for Denial of Service 
• Web Services Testing 
• AJAX Testing 
» 42+ Secure Mobile Development Best Practices 
(viaForensics)
OWASP Top 10 Mobile Risks 
Image from https://www.owasp.org/index.php/OWASP_Mobile_Security_Project#tab=Top_Ten_Mobile_Risks 
10 #ISC2Congress
iOS AppSec Cheat Sheet 
Image from https://www.owasp.org/index.php/IOS_Application_Security_Testing_Cheat_Sheet 
11 #ISC2Congress
Deconstructing .ipa Files 
12 #ISC2Congress 
» Download from app store 
• Mac OS X 10.7 Lion: ~/Music/iTunes/iTunes 
Media/Mobile Applications/ 
• Mac OS X 10.6: ~/Music/iTunes/Mobile 
Applications/ 
• Windows 7: C:UsersUsernameMy 
MusiciTunesiTunes MediaMobile Applications 
» Extract app to folder using 7-zip 
» Manually examine the files using 
Notepad++ or prgrep 
» Look for sensitive info (integration points) 
• Connection strings 
• Calls to Internet-facing web services 
• Calls to other local resources
13 #ISC2Congress 
iOS Target Files 
File name/extension Description 
.sinf Apple iOS digital rights management file 
.supp Apple iOS file (archives) 
.plist Apple property list XML file 
.nib Apple Interface Builder user interface 
resources 
.sqlite SQL Lite database file 
AppName <no extension> App file itself 
ChangeLog <no extension> No! Bad developer! Bad! 
PkgInfo <no extension> 4b package type + 4b app signature
Deconstructing .apk Files 
» Download from app store 
• Copy .apk file from rooted Android device to 
laptop via USB cable 
• Send .apk file from non-rooted Android 
device to Dropbox via APK Extractor 
• Alternately, you can download some .apk 
files from .apk archive sites 
» Extract app to folder using 7-zip 
» Manually examine the files using 
Notepad++ or prgrep 
» Look for sensitive info (integration 
points) 
• Connection strings 
• Calls to Internet-facing web services 
• Calls to other local resources 
14 #ISC2Congress
Android Target Files 
File name/extension Description 
Assets <folder> All your base are belong in here 
Lib <folder> .so files (third party libraries) 
META-INF <folder> .rsa, .fs, manifest.mf (hash values + certs = integrity) 
Res <folder> XML files and supporting graphics (how the app draws the 
15 #ISC2Congress 
interface) 
Templates <folder> Licenses, release notes, etc. 
AndroidManifest.xml Info that the device needs before it can run the app 
classes.dex Dalvik Executable (Exterminate! Exterminate!) 
resources.arsc Compiled application resources (strings, images, etc.)
Man-in-the-Middle 
» Plug laptop into wired network connection 
» Created an ad hoc wireless network on laptop 
» Connect mobile device to ad hoc wireless network 
» Start Wireshark on laptop 
• Capture ALL packets between mobile device and server 
» Use mobile device as a normal end user 
» Analyze Wireshark traffic 
• Unencrypted credentials 
• Unencrypted account information 
• Connection strings to servers (including third parties) 
» Alternately, use a proxy like Mallory (TCP) or 
16 #ISC2Congress 
Charles/Burp (HTTP)
iOS Reverse Engineering Toolkit 
17 #ISC2Congress 
Running iRET 
» Jailbreak your iDevice 
» Install supporting utilities 
» Install the target app 
on jailbroken iDevice 
» Open iRET app 
» Open the target app 
» Browse to 
http://deviceip:5555 
from your laptop 
Supporting Utilities 
» oTool 
» dumpDecrypted 
» Sqlite 
» Theos 
» Keychain_dumper 
» file 
» plutil 
» Class-dump-z
18 #ISC2Congress 
Vetting an App 
» Encrypted 
communications 
» Encrypted storage 
» Use of UUID 
» Analytics and ad 
services 
» Location services 
» Data sharing 
capabilities 
– Bluetooth 
» Access to… 
• Address book 
• Calendar 
• Reminder 
• Photos 
• Microphone 
• Social media services 
• Lock screen images 
• Cloud-based file sharing 
services
19 #ISC2Congress 
Vetting Support
20 #ISC2Congress 
Resources 
» Wireshark 
• http://www.wireshark.org/ 
» SQLite Database Browser 
• http://sourceforge.net/projects/sqlitebrowser/ 
» iPhone Backup Analyzer 
• http://www.ipbackupanalyzer.com/ 
» iOS Reverse Engineering Toolkit 
• http://blog.veracode.com/2014/03/introducing-the-ios-reverse- 
engineering-toolkit/ 
• https://www.veracode.com/iret-ios-reverse-engineering-toolkit 
» Charles Web Debugging Proxy 
• http://www.charlesproxy.com/
21 #ISC2Congress 
Resources 
» AXMLPrinter2 
• https://code.google.com/p/android4me/downloads/list 
» Android SDK + Android Developer Tools (ADT 
bundle) 
• http://developer.android.com/sdk/index.html 
» dex2jar 
• https://code.google.com/p/dex2jar/ 
» Java Decompiler (JD-GUI) 
• http://jd.benow.ca/ 
» Step-by-Step Guide to Decompiling Android Apps 
• http://slandail.net/step-by-step-guide-to-decompiling-android- 
apps/
22 #ISC2Congress 
Resources 
» Clueful 
• http://www.cluefulapp.com/ 
» viaProtect 
• https://www.viaprotect.com/ 
» Malwarebytes 
• https://www.malwarebytes.org/mobile/ 
» Lookout 
• https://www.lookout.com/ 
» MyPermissions 
• http://mypermissions.com/
23 #ISC2Congress 
Questions? 
Jerod Brennen, CISSP 
CTO & Principal Security Consultant, Jacadis 
LinkedIn: http://www.linkedin/com/in/slandail 
Twitter: https://twitter.com/slandail 
http://www.jacadis.com/ 
contact@jacadis.com

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Please, Please, PLEASE Defend Your Mobile Apps!

  • 1. Please, Please, PLEASE! Defend Your Mobile Apps! Jerod Brennen, CISSP CTO & Principal Security Consultant, Jacadis Strengthening Cybersecurity Defenders #ISC2Congress
  • 2. 2 #ISC2Congress Agenda » A Little Understanding Goes a Long Way » Mobile App Defense 101 » Attacking Your Own Apps » Vetting Apps » Resources
  • 3. How to Write Good Code From http://xkcd.com/844/ 3 #ISC2Congress
  • 4. Understand Your Environment » What development methodologies do we follow? » What programming languages do we use? » What risk/security frameworks do we follow? » What third-party libraries do we use? » What stages in the development process require approval from the security team? 4 #ISC2Congress
  • 5. Understand Your Platforms 5 #ISC2Congress » iOS » Android » BlackBerry » Windows
  • 6. Three Four Key Security Checks 6 #ISC2Congress » Defined Security Requirements – Project Plan – RFP, Contracts, etc. » Source Code Security Reviews – Manual Reviews – Reverse Binaries » Security Tests in QA • Positive AND Negative Test Cases » Analysis of “Deployed” Apps • Automated Scans • Manual Analysis
  • 7. Source Code Reviews (OWASP) 7 #ISC2Congress » Methodology (v1.1, current) • Preparation • Security Code Review in the SDLC • Security Code Review Coverage • Application Threat Modeling • Code Review Metrics » Methodology (v2.0, in development) • Preparation • Application Threat Modeling • Understanding Code Layout/Design/Architecture • Reviewing by Technical Control • Reviewing by Vulnerability • Security Code Review for Agile Development
  • 8. QA Security Test Cases 8 #ISC2Congress » Positive AND Negative » Top 10 Negative Test Cases • Embedded Single Quote • Required Data Entry • Field Type Test • Field Size Test • Numeric Bounds Test • Numeric Limits Test • Date Bounds Test • Date Validity • Web Session Testing • Performance Changes List from http://www.sqatester.com/methodology/Top10NegativeTestCases.htm
  • 9. Application Analysis » Automated scanning tools and manual analysis 9 #ISC2Congress » OWASP Testing Guide (v3) • Information Gathering • Configuration Management Testing • Authentication Testing • Session Management Testing • Authorization Testing • Business Logic Testing • Data Validation Testing • Testing for Denial of Service • Web Services Testing • AJAX Testing » 42+ Secure Mobile Development Best Practices (viaForensics)
  • 10. OWASP Top 10 Mobile Risks Image from https://www.owasp.org/index.php/OWASP_Mobile_Security_Project#tab=Top_Ten_Mobile_Risks 10 #ISC2Congress
  • 11. iOS AppSec Cheat Sheet Image from https://www.owasp.org/index.php/IOS_Application_Security_Testing_Cheat_Sheet 11 #ISC2Congress
  • 12. Deconstructing .ipa Files 12 #ISC2Congress » Download from app store • Mac OS X 10.7 Lion: ~/Music/iTunes/iTunes Media/Mobile Applications/ • Mac OS X 10.6: ~/Music/iTunes/Mobile Applications/ • Windows 7: C:UsersUsernameMy MusiciTunesiTunes MediaMobile Applications » Extract app to folder using 7-zip » Manually examine the files using Notepad++ or prgrep » Look for sensitive info (integration points) • Connection strings • Calls to Internet-facing web services • Calls to other local resources
  • 13. 13 #ISC2Congress iOS Target Files File name/extension Description .sinf Apple iOS digital rights management file .supp Apple iOS file (archives) .plist Apple property list XML file .nib Apple Interface Builder user interface resources .sqlite SQL Lite database file AppName <no extension> App file itself ChangeLog <no extension> No! Bad developer! Bad! PkgInfo <no extension> 4b package type + 4b app signature
  • 14. Deconstructing .apk Files » Download from app store • Copy .apk file from rooted Android device to laptop via USB cable • Send .apk file from non-rooted Android device to Dropbox via APK Extractor • Alternately, you can download some .apk files from .apk archive sites » Extract app to folder using 7-zip » Manually examine the files using Notepad++ or prgrep » Look for sensitive info (integration points) • Connection strings • Calls to Internet-facing web services • Calls to other local resources 14 #ISC2Congress
  • 15. Android Target Files File name/extension Description Assets <folder> All your base are belong in here Lib <folder> .so files (third party libraries) META-INF <folder> .rsa, .fs, manifest.mf (hash values + certs = integrity) Res <folder> XML files and supporting graphics (how the app draws the 15 #ISC2Congress interface) Templates <folder> Licenses, release notes, etc. AndroidManifest.xml Info that the device needs before it can run the app classes.dex Dalvik Executable (Exterminate! Exterminate!) resources.arsc Compiled application resources (strings, images, etc.)
  • 16. Man-in-the-Middle » Plug laptop into wired network connection » Created an ad hoc wireless network on laptop » Connect mobile device to ad hoc wireless network » Start Wireshark on laptop • Capture ALL packets between mobile device and server » Use mobile device as a normal end user » Analyze Wireshark traffic • Unencrypted credentials • Unencrypted account information • Connection strings to servers (including third parties) » Alternately, use a proxy like Mallory (TCP) or 16 #ISC2Congress Charles/Burp (HTTP)
  • 17. iOS Reverse Engineering Toolkit 17 #ISC2Congress Running iRET » Jailbreak your iDevice » Install supporting utilities » Install the target app on jailbroken iDevice » Open iRET app » Open the target app » Browse to http://deviceip:5555 from your laptop Supporting Utilities » oTool » dumpDecrypted » Sqlite » Theos » Keychain_dumper » file » plutil » Class-dump-z
  • 18. 18 #ISC2Congress Vetting an App » Encrypted communications » Encrypted storage » Use of UUID » Analytics and ad services » Location services » Data sharing capabilities – Bluetooth » Access to… • Address book • Calendar • Reminder • Photos • Microphone • Social media services • Lock screen images • Cloud-based file sharing services
  • 20. 20 #ISC2Congress Resources » Wireshark • http://www.wireshark.org/ » SQLite Database Browser • http://sourceforge.net/projects/sqlitebrowser/ » iPhone Backup Analyzer • http://www.ipbackupanalyzer.com/ » iOS Reverse Engineering Toolkit • http://blog.veracode.com/2014/03/introducing-the-ios-reverse- engineering-toolkit/ • https://www.veracode.com/iret-ios-reverse-engineering-toolkit » Charles Web Debugging Proxy • http://www.charlesproxy.com/
  • 21. 21 #ISC2Congress Resources » AXMLPrinter2 • https://code.google.com/p/android4me/downloads/list » Android SDK + Android Developer Tools (ADT bundle) • http://developer.android.com/sdk/index.html » dex2jar • https://code.google.com/p/dex2jar/ » Java Decompiler (JD-GUI) • http://jd.benow.ca/ » Step-by-Step Guide to Decompiling Android Apps • http://slandail.net/step-by-step-guide-to-decompiling-android- apps/
  • 22. 22 #ISC2Congress Resources » Clueful • http://www.cluefulapp.com/ » viaProtect • https://www.viaprotect.com/ » Malwarebytes • https://www.malwarebytes.org/mobile/ » Lookout • https://www.lookout.com/ » MyPermissions • http://mypermissions.com/
  • 23. 23 #ISC2Congress Questions? Jerod Brennen, CISSP CTO & Principal Security Consultant, Jacadis LinkedIn: http://www.linkedin/com/in/slandail Twitter: https://twitter.com/slandail http://www.jacadis.com/ contact@jacadis.com