Bug bounty: What is it and what to expect?

In this article, you will explore the bug bounty ecosystem and understand what to expect from it based on my experience during the last 4 years.

If you are barely starting in the infosec industry and want to start doing bug bounties, I recommend you check out the OWASP Top 10 vulnerabilities in practice, which is a guide to the basics of web application security testing. For now, let’s get you ready to start hacking and getting paid. But first, let’s understand the whole picture.

Imagine a world where companies come to you and ask you to hack them. In return, they will pay you whenever you find a unique vulnerability. And the best part, you don’t have to neither leave your home nor stick to a time schedule!
It sounds unrealistic, right? Well, let me tell you that it’s now a real job, not a fantasy anymore!

When bug bounties didn’t exist

Let’s travel 50 years back. Home computers barely start entering the market. Phone phreaking at its golden age. Hackers painted as cybercriminals and weird people who think outside the norm to cause trouble. The US government passes laws which make it a crime to break into computer systems. I wasn’t yet born, and I’m honestly grateful for that.
Unfortunately, companies neglected hackers and continued bringing products to the world without proper security testing. The situation got to a point where the real cybercriminals saw benefits in compromising the vulnerable companies, and hacking companies they did!

Bug bounty programs to the rescue

Luckily, some major companies felt the need to embrace the hacker spirit and leverage the hacking skills of independent individuals.

The birth of the “bug bounty” term

Back in 1995 the Netscape Communications Corporation company came up with the term “bug bounty” for the first time. Do you remember the Netscape browser? You probably don’t, but it’s the grandfather of modern Web Browsers like Chrome and Firefox. Well, back in the days, the company launched a bug bounty program for the Netscape Navigator 2.0 Beta browser. We had to wait for about 15 years before major companies started creating their own programs. We are talking about Google and Facebook in about 2011. Yahoo! Followed in 2013.

Early baby steps

However, this model had its limitations due to the fact that those programs weren’t mature enough.

First, the rewards were as modest as a t-shirt! Don’t get me wrong, I have nothing against t-shirts, I was so grateful to receive one from SoundCloud after I found a bug, but let’s just say that there are many other factors which drive hackers. According to the 2020 HackerOne Hacker report, 53% hack for money.

Secondly, the programs were limited to only a few companies, meaning that hackers didn’t have enough choice. You either hack Facebook or go to jail hacking others. And this is a big downside because 68% of bug bounty hunters hack for the challenge and the opportunity to learn, according to the same report.

Last but not least, hackers didn’t have a middleware party to defend their bugs if the program didn’t play fair. This doesn’t happen very often, but it can lead to surprising outcomes. In 2013, a hacker wrote a poorly-written report to Facebook about a bug which allowed an attacker to post on an arbitrary Facebook user’s timeline. When Facebook didn’t acknowledge the vulnerability, he then posted a message on Mark Zuckerberg’s timeline. Consequently, he wasn’t eligible for a reward. This is a common issue; when working as a triage analyst at HackerOne, I can’t count the number of poorly-written reports that I had to handle. But of course, it’s not an excuse not to give it enough analysis time and honor the hacker’s effort.

The rise of Bug bounty platforms

With all the limitations that traditional bug bounty programs suffered from, there was a need for middleware in the cybersecurity market to help hackers and companies collaborate with each other. Naturally, bug bounty platforms were born to shape a new era in cybersecurity. HackerOne and Bugcrowd were among the first players, but we’ll leave details about each one to another episode. However, they all share pretty much the same core features.

Gamification of hacking

Hacking with bug bounty platforms is like playing a video game. We find vulnerabilities and increase our metrics, which increases our ranking in the leaderboard and opens the door to new programs, new challenges and new experiences. The best part is that we get paid along the way. Programs also get rated, the more active and rewarding they are, the more luckily talented hackers will help them stay secure. It’s a win-win situation.

Bug bounty platform HackerOne 90 Days Leaderboard
Bug bounty platform HackerOne 90 Days Leaderboard

Bug bounty challenges

More and more companies are joining bug bounty platforms, and so it is for people who want to hack. The problem is that not many of them have proper hacking knowledge. It’s easy to see how this is unbalanced. In fact, a bug bounty ecosystem relies on the abundance in both good programs and talented hackers. That’s why those platforms are developing more and more educational content in the form of videos, mini-challenges and CTFs. An example of that is the LevelUp conference which Bugcrowd organizes each year. It hosts talks from great hackers who share updated hacking knowledge. Another example is HackerOne’s hacktivity and the hacker101 website where Hackerone publishes new disclosed reports and provides a free playground for hackers to solve challenges and get private invites.

Bug bounty Hacker101 CTF challenges
Bug bounty Hacker101 CTF challenges

Bug bounty events

Another interesting advantage those platforms bring to the table is live hacking events. They gather the best hackers for a weekend to hack a target onsite. It’s a great experience which brings people together and produces new meaningful relationships. I once received an invitation but I turned it down due to some family health struggles I was going through. It was a big disappointment for me not to attend it, but I didn’t have a choice in that situation. Personally, family comes first.

The Bug bounty community

So far, bug bounty platforms are emerging and they are doing a great job at educating the next generation of hackers. Hunting for bugs has become a trend of its own and the community is growing so fast. In fact, about a third of the hacking crowd have less than 2 years of experience according to the HackerOne Hacker report of 2020. Naturally, the community started building its own knowledge base. New blogs, YouTube channels, live streams and podcasts started bringing even more educational and entertaining content. Allow me to talk about three valuable things that the community has produced.

Bug bounty methodologies

Hacking is an Art, each hacker has a perspective, a set of skills and experiences which shape the methodology he or she follows when approaching a target. Consequently, it is so easy to get lost in the number of clever methodologies out there. Jason Haddix was one of the early hackers who shared his bug bounty methodology, which is now at its 4th version.

Bug bounty tools

Every craftsman is nothing without a proper toolbox, and hackers are no exception. The bug bounty community is producing so many tools that you will have a hard time tracking. By the way, that’s a major reason why Jason’s bug bounty hunting methodology has been revised four times since 2015.

Bug bounty books

For those who enjoy reading, there are many books which will teach you just how to get into the game of bug bounties. One of the first ones was Peter’s Web hacking 101. I downloaded a free copy when signing up with HackerOne, and boy was it helpful! Shout out to Peter Yaworsky from here!

For those who don’t enjoy reading, you better get used to it if you want to survive in this career.

Bug bounty benefits

Bug bounty is proving its spot in the cybersecurity market, that’s for sure. It is becoming another way of securing companies through an increasing crowd of hackers. It is useful in many ways.

Bug bounty money

The rise of bug bounty platforms and the increasing public breaches led to a significant increase in the rewards. I receive now and then emails from HackerOne telling me that a program has increased their rewards either for a promotion period or indefinitely. In one live hacking event, payouts surpassed a Million dollar amount! Think about that! A million dollar in just three days!

Freedom and flexibility

Bug bounty hunting allows hackers to live the working lifestyle they feel comfortable in. All the work is done remotely, except for live hacking events, which due to the Corona Virus, has also gone online. We can work alone or collaborate. Flexibility to work late at night or early in the morning is a great benefit. We also can choose from a wide range of programs depending on our preference. Although the majority prefers to make a side hustle income, around 20% work as full-time bug bounty hunters.

Relational dimension

Bug bounty hunting is not just all about making money. In fact, hackers build relationships and expand their friendships and professional network. The bug bounty community is generally open-minded with a young heart. People here are curious, fun and hard-working. We support each other in case someone goes through a hurdle, like a burnout (more on this shortly). Overall, I’d say I’m grateful to be part of such a great community.

Bug bounty drawbacks

Bug bounties cannot be that perfect, can they? There are downsides as well. I feel I’m responsible to put your expectations into perspective and give you a heads up before you leave your job and start hunting for bugs. Bug bounties, like any other thing in this life, has its drawbacks as well.

Instability

When we hunt for bugs, we only get bounties when we are the first to find one, that’s just how it is. This rule brings a great deal of income instability because it generates frustration and fear. Even talented hackers can hunt for days, or even weeks, without finding a single bug. Imagine how frustrating this can be! That’s why the majority prefer to hack part-time.

Isolation and comparisons

Because bug bounty hunting is commonly remote, we are not limited to an office. Some hackers travel the world while hacking. Others prefer to enjoy hunting from the comfort of their couch at home. However, since we don’t have to work with a team, we can sometimes feel lonely. And when we don’t find vulnerabilities, it gets even worse, especially when scrolling the Twitter feed and finding many tweets of others who find bugs and get paid.

Depression and burnout

The aforementioned drawbacks help prepare for the coming of the scariest ghost, the darkest nightmare of all bug bounty hunters, the most wild beast which we call the burnout. You know, the feeling when you work continuously without any results, you lock yourself in front of your machine, you hack day and night and all you see are others finding bugs. Therefore, you lose your confidence and hope doors suddenly get closed. And then the time comes, and you decide to stop everything and never get back to hacking again.

That’s why it is important to pay attention to your mental health while working as a bug bounty hunter. We will talk about that on a dedicated episode. Meanwhile, you can read what other bug bounty hunters think about it. 

Now you know what to expect from bug bounty hunting. Next time, we will talk about your mental health and how it helps avoiding burnout. Until then, stay curious, keep learning and go find some bugs.