Workshop: Secure Software Development: From Rookie to Hardcore in 90 Minutes

demo project:
https://github.com/vixentael/ios-datasec-basics

1. Intro (Apple, OWASP, jailbreaks)
2. Secure software development lifecycle
3. Stored data mistakes: key management and encryption
4. Practice time
5. Other data security things (network, logging, screenshots)
6. Reading list

Other talks and videos:
https://github.com/vixentael/my-talks

1. Secure software development: from rookie to hardcore in 90 minutes iOS data security workshop @vixentael
2. Secure software development: from rookie to hardcore in 90 minutes iOS data security workshop @vixentael
3. @vixentael product engineer in security and cryptography started from iOS 3 OSS maintainer: Themis, Acra conduct workshops & training about secure apps development training.cossacklabs.com
4. https://medium.com/@vixentael/popular-note-taking-apps-share- these-security-flaws-security-tips-for-developers-326180e41329 @vixentael
5. https://github.com/vixentael/ ios-datasec-basics @vixentael
6. Plan for next 85 mins: 1. Intro (Apple, OWASP, jailbreaks) @vixentael 2. Secure software development lifecycle 3. Stored data mistakes: key management and encryption 4. Practice time 5. Other data security things (network, logging, screenshots) 6. Reading list
7. Secure software development Apple (guidelines, rejection guides) users (upset, angry) money (breaches, legal actions, fines) why care anyway? @vixentael
8. http://headway.io/blog/apple-app-store-new- privacy-policy-what-you-need-to-know/ New App Store privacy policy - minimize the data you collect - be transparent on how you use the data - protect stored and transit data - remove data fully and quickly @vixentael
9. GDPR @vixentael Article 32/35: responsibly store and process data according to risks
 
 Article 33/34: detecting data leakage and alert users & controller https://gdpr-info.eu/
10. @vixentael https://gdpr-info.eu/ Article 32
11. OWASP Top-10 mobile risks www.owasp.org/index.php/OWASP_Mobile_Security_Project @vixentael • M1: Improper Platform Usage • M2: Insecure Data Storage • M3: Insecure Communication • M4: Insecure Authentication • M5: Insufficient Cryptography • M6: Insecure Authorization • M7: Client Code Quality • M8: Code Tampering • M9: Reverse Engineering • M10: Extraneous Functionality
12. OWASP Top-10 mobile risks • M1: Improper Platform Usage • M2: Insecure Data Storage • M3: Insecure Communication • M4: Insecure Authentication • M5: Insufficient Cryptography • M6: Insecure Authorization • M7: Client Code Quality • M8: Code Tampering • M9: Reverse Engineering • M10: Extraneous Functionality www.owasp.org/index.php/OWASP_Mobile_Security_Project @vixentael
13. Remote jailbreak iOS11 (patched in iOS12) https://twitter.com/kevin_backhouse/status/1057352656560287746 @vixentael
14. www.apple.com/business/site/docs/iOS_Security_Guide.pdf @vixentael 95 pages PDF
15. Most users trust sensitive data to your app regardless of how well you protect it.
16. Secure development lifecycle methodology MS SDL OWASP S-SDLC microsoft.com/en-us/sdl owasp.org/index.php/ OWASP_Secure_Software_Develop ment_Lifecycle_Project @vixentael
17. Define sensitive data Design & implement security controls Verify security controls
 (testing, monitoring) SSDLC in a simple words @vixentael @vixentael during planning during planning & implementation acceptance testing / QA, unit testing during planning during planning & implementation acceptance testing / QA, unit testing
18. @vixentael @vixentael SSDLC in a simple words Define sensitive data Design & implement security controls Verify security controls
 (testing, monitoring) during planning during planning & implementation acceptance testing / QA, unit testing repeat
19. So, one by one
20. Sensitive data @vixentael @vixentael
21. Sensitive data @vixentael @vixentael geo-locations health data financial data kids locations cars remote control credentials logs PII
22. – any kind of data, that will break business objectives or prosperity of those who use data, if leaked. Sensitive data @vixentael @vixentael geo-locations health data financial data kids locations cars remote control credentials logs PII
23. Defining sensitive data: sensitive user data (PII, password) regulations (GDPR / HIPAA / PCI DSS) tech data (keys, logs, accesses) https://www.cossacklabs.com/blog/what-we-need-to-encrypt- cheatsheet.html @vixentael @vixentael
24. @vixentael @vixentael Security controls
25. Data security Application security Infrastructure security Monitoring Intrusion detection Vulnerability management @vixentael Security controls proactive and reactive
26. Proactive controls Data security encryption Access security authentication, firewalls, OS Node security firewalls, compartmentalization, isolation, OS @vixentael
27. Data security key management, integrity checks, authenticated crypto Access security credential management, access logging, jailbans Node security code security, monitoring, SIEM Reactive controls @vixentael
28. Verification, testing @vixentael @vixentael https://github.com/OWASP/owasp-mstg OWASP Mobile Security Testing Guide https://github.com/OWASP/owasp-masvs OWASP Mobile Application Security Verification Standard
29. MASVS @vixentael @vixentael
30. @vixentael @vixentael SSDLC again Define sensitive data Design & implement security controls Verify security controls
 (testing, monitoring) during planning during planning & implementation acceptance testing / QA, unit testing repeat
31. Storage encryption and key management
32. File and CoreData encryption https://developer.apple.com/documentation/uikit/core_app/ protecting_the_user_s_privacy/encrypting_your_app_s_files NSPersistentStoreFileProtectionKey @vixentael @vixentael
33. Store encrypted data: Encrypt stored data UserDefaults Files Database cells Backups @vixentael @vixentael
34. Symmetric encryption with integrity checks and long key AES-256-GCM Encrypt stored data @vixentael Use strong encryption
35. Symmetric encryption, mistakes @vixentael @vixentael wrong data scope poor encryption flow design bad key management bad cryptography encryption lib mis-use
36. Hashing: md5 vs sha256 @vixentael @vixentael https://passwordsgenerator.net/sha256-hash-generator/
37. ☠ md5 ☠ sha1 bcrypt https://dusted.codes/sha-256-is-not-a-secure- password-hashing-algorithm PBKDF2 sha256 sha512 HKDF @vixentael Wanna hash password? Use KDF
38. https://www.raywenderlich.com/129-basic-ios-security-keychain- and-hashing @vixentael Use KDF
39. https://github.com/OWASP/CheatSheetSeries/blob/master/cheatsheets/ Password_Storage_Cheat_Sheet.md @vixentael should be random should be > 10k Use KDF correctly
40. https://pdos.csail.mit.edu/papers/cryptobugs:apsys14.pdf 269 CVEs from 2011-2014 17% 83% bugs inside crypto libs misuses of crypto libs by individual apps @vixentael
41. @vixentael @vixentael Even more mistakes XORing != encrypting using password as encryption key (without KDF) storing keys elsewhere use single encryption key for all data/users
42. @vixentael @vixentael Use encryption
43. @vixentael @vixentael should be random should use KDF(key) uses AES CBC, not AES GCM padding? salt? Use encryption correctly
44. Use “boring” crypto libraries ★ use strong & audited crypto ★ work everywhere ★ hide cryptographic details ★ hard to mis-use ★ have integration with key storage @vixentael https://speakerdeck.com/vixentael/dont-waste-time-on-learning- cryptography-better-use-it-properly
45. Encryption that hard to mis-use @vixentael @vixentael Themis
46. Encryption that hard to mis-use @vixentael @vixentael hides cryptographic details: salt, IV, KDF, padding built-in KDF, safe to use passphrase uses AES-256-GCM Themis
47. Storage Transport Multi- platform themis libsodium tink TLS
 themis libsodium OTRKit
 libsignal Made for one platform, some ports available RNCryptor CryptoSwift CommonCrypto https://www.cossacklabs.com/choose-your-ios-crypto.html @vixentael @vixentael
48. Key management APP TOKENS USER PASSWORDS PUBLIC CERTS let apiToken = “63ufHs2E82-cJgsm!djr7-Ks1TTYC4TV” let appId = "VK1TTYC4TV" let poolId = “us-east-1:r0s3s4r3-r3d-13375p34k" var userPass = "qwertyqwerty" @vixentael
49. APP FLOW BUILT-IN Keychain - KDF - encrypt @vixentael plist/files - encrypt - obfuscate - calculate
50. Practice time
51. https://github.com/vixentael/ ios-datasec-basics @vixentael
52. Built-in keys store as hardcode variable store obfuscated in plist, de-obfuscate on start store encrypted in plist, decrypt on start @vixentael
53. App flow keys store as memory variable store obfuscated/encrypted in User Defaults store in Keychain, protect by Biometrics @vixentael
54. https://github.com/vixentael/ ios-datasec-basics @vixentael
55. Other data security things
56. Transport encryption github.com/ssllabs/research/wiki/SSL-and-TLS- Deployment-Best-Practices private keys RSA-2048, ECDSA-256 obtain certificate from reliable CA TLS v1.3-v1.2 use secure cipher suites TLS_ECDHE_ECDSA_WITH_AES_ 256_GCM_SHA384 ✅ enable Forward Secrecy ✅ enable HSTS (web) . rotate certificates often @vixentael
57. SSL pinning Moya owasp.org/index.php/Pinning_Cheat_Sheet @vixentael
58. Update certificate Update app with hardcoded certificate Built-in several certificates Update from server: build trusted channel @vixentael SSL pinning
59. transport = Transport() transport?.setupKeys(serverId, serverPublicKey: serverPublicKey) session = TSSession(userId: clientIdData, privateKey: clientPrivateKeyData, callbacks: transport!) startSession(clientId: clientId, message: connectionMessage) Encrypt over SSL Themis @vixentael
60. Themis axolotl noise @vixentael Encrypt over SSL
61. medium.com/@AyunasCode/how-to-hide-your-api-keys-367ef6589949 shanirivers.me/posts/hiding-your-api-keys-for-ios-projects orta/cocoapods-keys awslabs/git-secrets keys.plist → .gitignore Do not commit secrets @vixentael
62. Do not log secrets cfpb/clouseau Automate checking code for forgotten secrets. @vixentael
63. @vixentael https://speakerdeck.com/vixentael/x-things-you- need-to-know-before-implementing-cryptography
64. Do’s and Don’ts
 of secure development
65. DON’T - Do things just because “they make security better” - Copy-paste from StackOverflow - Implement your own security controls where 
 solutions are available @vixentael
66. DO - Only things that address real valid risks - Use industry’s best practices, standards and tools - Explain why spending effort is necessary - Plan, implement, test, formalize - Watch the trends, follow experts @vixentael
67. Reading, watching
68. General theory http://mashable.com/2016/04/16/apple-security-explained/ How Apple Security works https://medium.com/@vixentael/popular-note-taking-apps-share-these-security-flaws-security- tips-for-developers-326180e41329 Popular note-taking apps share these security flaws https://medium.com/@cossacklabs/apple-export-regulations-on-crypto-6306380682e1 Apple Export Regulations on Cryptography https://howhttps.works/ How HTTPS works: cats
69. Cryptography https://www.owasp.org/index.php/Cryptographic_Storage_Cheat_Sheet Cryptographic Storage Cheat Sheet https://www.owasp.org/index.php/Key_Management_Cheat_Sheet Key Management Cheat Sheet https://developer.apple.com/library/content/documentation/Security/Conceptual/ cryptoservices/KeyManagementAPIs/KeyManagementAPIs.html Managing Keys, Certificates, and Passwords https://cossacklabs.com/choose-your-ios-crypto.html Crypto in iOS: choose your destiny
70. Testing http://iphonedevwiki.net/index.php/Crack_prevention Crack prevention https://mobile-security.gitbook.io/mobile-security-testing-guide/ios-testing-guide/0x06a- platform-overview Mobile Security Testing Guide https://github.com/OWASP/owasp-masvs OWASP Mobile Application Security Verification Standard
71. Talks & training github.com/vixentael/ my-talks training.cossacklabs.com
72. @vixentael product engineer in security and cryptography conduct workshops & training about secure apps development