I often have conversations with people about being anonymous specifically while on the Internet. Most people believe that anonymity is not possible today. Others believe that by doing specific steps (deleting your browser history, ensuring SSL is active are two of many examples) you will not be traced. In my opinion and experience both points of view are correct. While there is never a 100% guarantee of being totally anonymous, you can take steps to improve your anonymity. The first step to being anonymous is to understand that anonymity it is not black and white. There are lots of questions you have to assess and answer. What is the situation you find yourself in? Why do you want to remain anonymous in the situation? Who may try to discover your identity in that situation? How badly will someone or a group want to obtain your true identity? What resources and intelligence do you you have at your disposal to protect your anonymity? What resources and intelligence does the individual or group that would want to discover who you really are have available to them? These are but a few of the many questions and their applicability depends on the situation.
A good analogy to anonymity is basic physical security. I have security at my home, the doors lock, the windows close and lock, only certain people have keys, there is an alarm system. If you compare my home security to the home security of a criminal organization’s leader, you can be certain they will have more security than I do in my home. They may have people standing post watching all sides of the house, large perimeter fences with alarms, bullet proof windows, steel doors with re-enforced frames, hired bodyguards through the home, rehearsed escape plans with get-away vehicles and whatever else they deem necessary. You can walk up to my front door and ring the doorbell, I might even answer if I am home. You would have to first find the home of the leader in a criminal organzation. They probably have multiple homes, so you would have to determine which one they were in at a particular time. Assuming you could accomplish that, you probably will not make it to the front door if you were to try let alone have the leader answer the door if you were able to physically get to the door. It is not just that the criminal organization has way more money than I do as to why they have better security. It is because they have something that is of much higher financial value than I do. A criminal organization that has something of value to protect (merchandise, leader, industry knowledge) and is willing to spend more money on security because the risk of loosing what they are protecting is greater. Security is the same with any organization be it financial, private, pharmaceutical, mining, government, or whatever. What are the most treasured items or knowledge I have to protect? How much do I have to loose if those items or knowledge was stolen or obtained? What is an acceptable level of risk for loosing this property or knowledge? What will the cost of security be to get to an acceptable level of risk?
Anonymity is no different. If I want to purchase a gift for a family member that costs $100. I can spend hours, setting up tunnelling protocols, configuring a special browser and operating system, setting up an untraceable method of payment so that I can place my order knowing with confidence that my family, my ISP, law enforcement, and anyone else won’t know (at least not without a lot of time and money on their part). I may have to learn how to do all this. But even if someone does know it takes time to set this up, check that it is in fact secure. For me, that time is worth more than the $100 dollars I am spending on the gift. I’d probably just order it on a normal PC, using a normal Internet connection, clear the browser history, and hope no one sees the credit card statement before the gift arrives. Could my ISP see that I ordered flowers? If they wanted to yes. Do I care? Not really.
But what if I want to browse a particular website and not have Google know about it? What if I wish to do research on a particular topic that I don’t want any person, group or company knowing that I am interested in that topic? What if I am conducting an investigation into an individual who works for a company and we know he is technically savvy and has an intricate knowledge of security? In those cases, it is worth my time to plan properly so the risk of being exposed is reduced. These questions and how to will be the topic of a series of blog posts I will write entitled “So, you want to be anonymous.” I am not sure how many posts will be in the series yet (I suspect 4 or 5), but I will try to keep each post short and cover one topic of maintaining anonymity. Anonymity on the Internet is something that has always interested me and many others. There is lots of information on the Internet about it (both true and false information). I used to have to keep up with being anonymous in order to do some of the work I have done in the past. Today, I mainly keep up with it, just because it interests me. The next posts in this series will start with a general discussion on a few of the basic ways you can be monitored from the network as well as application levels. Next we can discuss ways to avoid being monitored, minimize digital trace evidence that can lead back to a particular target from the network, service, and application perspective.
Series Index:
1. Your IP Address, the low hanging fruit













