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Nathan Vaz – John Doe and the Pigeon Tails

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Nathan Vaz – John Doe and the Pigeon Tails John Doe and the Pigeon Tails Nathan Vaz The purpose of this project is to create a solution for users to communicate securely and privately over the Internet. Through creating bootable USB disks running secure Linux-based operating systems, Tails and JonDo-LiveDVD; the project will then test the capabilities of Internet traffic anonymiser services such as Tor and JonDo through an instant messaging (IM) application. The project will also explore the role of authentication over using the Off-the-Record (OTR) plugin extension. ITNET306A – Major Project Individual J. Doe & Pigeon Tails Table of Contents INTRODUCTION .............................................................................................................................. 4 LITERARY REVIEW .......................................................................................................................... 5 BACKGROUND ....................................................................................................................................... 5 SPY VS. (SPY) ........................................................................................................................................ 6 APPLICATIONS ....................................................................................................................................... 6 PLATFORMS .......................................................................................................................................... 7 TECHNOLOGIES ...................................................................................................................................... 8 MATERIALS ................................................................................................................................... 10 HARDWARE ........................................................................................................................................ 10 USB Flash Drives .......................................................................................................................... 10 Computer .................................................................................................................................... 10 OPERATING SYSTEMS ........................................................................................................................... 10 Tails OS ........................................................................................................................................ 10 JonDo-LiveDVD ............................................................................................................................ 10 SOFTWARE ......................................................................................................................................... 11 Virtual Box ................................................................................................................................... 11 KeyPassX ..................................................................................................................................... 11 PiDgin .......................................................................................................................................... 11 VeraCrypt .................................................................................................................................... 11 JonDo/JAP ................................................................................................................................... 12 METHOD ....................................................................................................................................... 13 TAILS PLATFORM ................................................................................................................................. 13 JONDO-LIVEDVD PLATFORM ................................................................................................................ 22 FIRST LAUNCH ..................................................................................................................................... 23 Tails ............................................................................................................................................. 23 JonDo-LiveDVD ............................................................................................................................ 24 MOUNTING: ....................................................................................................................................... 28 JONDO .............................................................................................................................................. 29 PIDGIN .......................................................................................................................................... 31 TAILS ................................................................................................................................................. 31 JONDO-LIVEDVD ................................................................................................................................ 33 PIDGIN OTR Q&A ............................................................................................................................... 35 Nathan Vaz ITNET306A - Major Project Page 2 of 60 J. Doe & Pigeon Tails USER INSTRUCTIONS ..................................................................................................................... 38 TAILS ................................................................................................................................................. 38 JONDO-LIVEDVD (PC ONLY) ................................................................................................................. 39 USING PIDGIN AND OTR ....................................................................................................................... 41 Not Private .................................................................................................................................. 41 Start Private ................................................................................................................................ 42 Why Private? ............................................................................................................................... 46 RESULTS ........................................................................................................................................ 47 STICK 1: RED ....................................................................................................................................... 47 STICK 2: BLUE ..................................................................................................................................... 48 STICK 3: GREEN ................................................................................................................................... 49 CONCLUSION ................................................................................................................................ 51 REFERENCES .................................................................................................................................. 52 APPENDICES .................................................................................................................................. 55 APPENDIX 1 – RED ............................................................................................................................... 55 APPENDIX 2 – BLUE ............................................................................................................................. 57 APPENDIX 3 – GREEN ........................................................................................................................... 59 APPENDIX 4 – YELLOW ......................................................................................................................... 60 Nathan Vaz ITNET306A - Major Project Page 3 of 60 J. Doe & Pigeon Tails Introduction Whilst many Internet users currently communicate with each other or access various web services without much consideration for data privacy, the aim of this project is to change the perspective of those types of users. This project features instructions on how to create a system of communication that can remain as private as possible both over the Internet and even on users’ own hardware. Essentially, this project creates a network of users that can securely communicate with each other over the Internet and even have a method of authenticating the other users without the need for any unsecure side-channels (other methods of communication). The technologies that are chosen for this project also enable the communication to not be recorded or logged by other users or third parties. The way that this project is constructed also allows for the quick deletion of what a user is doing. The overall structure of the final product will look something like; A USB stick A Bootable “Live” operating system A secure Internet traffic anonymiser An Instant Messenger (IM) application An encrypted partition Pre-authorised users Encrypted authentication methods Although the usage scenarios for the end product could be considered potentially nefarious, however the portion of the wider user population that value their privacy a lot would find this project an interesting experiment on how to go relatively “Low-Fi” with Internet communications. Nathan Vaz ITNET306A - Major Project Page 4 of
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