Digital Privacy and Anonymity

..with tools!

A Primer:

  1. Why care about privacy?
  2. Some use cases for anonymity tools
  3. Operational Security
  4. Tor Browser
  5. TAILS Operating System
  6. Other Considerations

DeadDrop and Aaron Swartz's legacy.

Digital surveillance affects..

  • Journalists & Researchers
  • Activists
  • Whistleblowers
  • Artists
  • Students
  • Workers

..all of us.

SNOWDEN: Yes, he's on his laptop. And we're looking at the man behind the device. And in his lap is a little boy, a toddler, who's just playing on the keyboard. And the father's smiling. And the little boy looks at the webcam. It's just a glimpse, but to me it seems as though he's looking at me. And it reminds me of my childhood, of learning about technology with my own father. And I realize this man has done nothing wrong. He's just trying to get a job. He's just trying to study. He's just trying to get through life like all of us are. And yet, he's caught up. His children are caught up. We are all caught up by a system that we were not allowed to know existed.
The trouble is, targeted surveillance frequently includes the indiscriminate collection of the private data of people targeted by race but not involved in any crime. For targeted communities, there is little to no expectation of privacy from government or corporate surveillance. Instead, we are watched, either as criminals or as consumers. We do not expect policies to protect us. Instead, we’ve birthed a complex and coded culture—from jazz to spoken dialects—in order to navigate a world in which spying, from AT&T and Walmart to public benefits programs and beat cops on the block, is as much a part of our built environment as the streets covered in our blood.

What's "wrong" is not objective, and surveillance builds haystacks to find needles.

Even if you "aren't doing anything wrong", surveillance alters people's state of mind.

Similar to the state you enter when there's a police cruiser behind you.

So why would I want to practive digital privacy and anonymity anyways?

Reasons people have used digital anonymity tools:

  • Delicate research
  • Dodging intrusive tracking
  • Censorship Circumvention
  • Communications
  • Submitting info anonymously
  • Peace of mind
Under state/corporate internet censorship, many users turn to Tor.

"Average number of trackers seen on selected government websites from the WhoTracks.Me September dataset."

Before exploring tools, we need to talk about OPSEC.

In every instance, it is the lack of compartmentation between accounts and personas that has been the cause of the pain. Without proper compartmentation, attackers are able to leverage information from one compromised account to access another related account. ..At a bare minimum — keep your business and personal life (and accounts) separate.

OPSEC in five steps:

  1. Identification of Critical information
  2. Analysis of Threats
  3. Analysis of Vulnerabilities
  4. Assessment of Risk
  5. Application of proper measures

Things to be careful doing with anonymizing software:

  • Banking
  • Use of personal/work accounts (email, slack, etc)
  • Registering to services with similar usernames as your other accounts
  • Stray away from posting personal details on public forums
  • Giving up a heap information on a small network while being the only one using tor on said network
SHA2017 presentation: "How [have] people their anonymity? Let's study real-world cases and try to learn how to avoid these errors."

While sometimes it might be best to absolve from doing these things at all while using anonymity tools, there are ways to do them safely through a bit of "compartmentalization"

  • Using different circuits and/or sessions
  • Always ensuring authentication and sessions for these are done through HTTPS sites (encryption!)
  • The Tor Browser

    What is it?

    • An anonymized browser based on Firefox
    • Works with Windows, MacOS, and Linux distros
    • Tunnels all the browser traffic through the Tor Network
    • Access to anonymous "Onion sites"
    • Removes all cookies and web data after closing
    • "..private access to an uncensored web."

    How does it work?

    tl;dr - Multiple hops through these circuits allow anonymization of your actual IP address

    NoScript and HTTPS Everywhere addons

    Blocks scripts and enforces encryption, respectively.

    Preferences: Security Level
    Bridges for traffic obsfucation
    By default, Tor is set to automatically update to its latest version. You will be prompted to restart.
    Updates are important! They patch major security vulnerabilities and other bugs. You can also check for updates within about:preferences.

    Tor has mobile clients!

    Be _very_ careful with un-official Tor apps - these are often fake and created to track users/spread malware.


    What is it?

    • A bootable OS where _all_ network traffic within the system is routed through the Tor Network
    • Fits on a USB over 8GB
    • Stocked with several helpful privacy and security applications/tools
    • Leaves no trace of system logs/files on the computer you boot from
    • Wipes metadata and logs from the bootable USB
    MAC addresses are unique identifiers for machine's on a network. An administrator on the network can find out "who you are" by your MAC. TAILS allows you to "spoof" a fake MAC address before connecting to anything.
    TAILS uses a clean Gnome desktop environment.
    Once the system finished automatically connecting to the Tor network, you can check you Tor Circuit connectivity details with the Onion Circuits application.
    A terminal is available for you, if you're into that.
    Managing files for anonymous sharing, security, etc is relatively simple.
    TAILS includes a great "purging" application called MAT2 (Metadata Anonymisation Toolkit v2)

    What is metadata?

    EFF: Metadata (or "data about data") is data that describes a piece of information, apart from the information itself. So the content of a message is not metadata, but who sent it, when, where from, and to whom, are all examples of metadata. Legal systems often protect content more than metadata: for instance, in the United States, law enforcement needs a warrant to listen to a person's telephone calls, but claims the right to obtain the list of who you have called far more easily. However, metadata can often reveal a great deal, and will often need to be protected as carefully as the data it describes.
    You can use MAT2 in terminal - works great against some metadata, but won't clean up things like watermarks, .xls files, etc.
    Your TAILS bootable can be created with persistent storage. This means that you can have a password-protected and encrypted drive partition for file storage, software settings, encryption keys, etc. This will help the system "remember" where you last left off, alternative to the default of starting from a "clean slate".

    Please do keep in mind the following drawbacks related to persistence on a TAILS drive:

  • An attacker will be able to observe the existence of the persistant partition - it is not hidden
  • It is _highly_ recommended you do not alter system and/or application configuration files for security reasons
  • If you go this route make sure to use a strong paassword
  • Other Considerations

    Physical access means "game over". Machine configurations such as Full Disk Encryption can only partially help protect against this.

    Leaving no traces might seem over-paranoid, but in may cases its worth going to these measures.

    Threat modeling is useful.

    EFF: A way of thinking about the sorts of protection you want for your data so you can decide which potentional threats you are going to take seriously. It's impossible to protect against every kind of trick or adversary, so you should concentrate on which people might want your data, what they might want from it, and how they might get it. Coming up with a set of possible threats you plan to protect against is called threat modeling or assessing your risks.

    Tor Project's official documentation is your friend!

    Thank you, and stay safe.