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5 of the most challenging puzzle quests on the internet – ANITH
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5 of the most challenging puzzle quests on the internet

5 of the most challenging puzzle quests on the internet

Photo credit: Unsplash

There are those who enjoy the occasional bout of Sudoku, and then there are those who dedicate their lives to unraveling the toughest games on the internet. But some of these elaborate puzzle quests are no ordinary brain teasers. They are highly technical problems that require specific knowledge in areas such as mathematics, cryptography, and programming.

Such online puzzles are perfect for sussing out the brainiacs and Sherlock Holmeses of the world. That’s why companies and even government organizations are using them to identify talent and attract the best of the best. Here are five of the most challenging puzzles that reward winners with either a once-in-a-lifetime career opportunity or a lifetime of bragging rights.

1. Cicada 3301

Once dubbed the hardest puzzle on the internet, Cicada 3301 has stumped the world’s brightest minds since 2012. Its puzzles involve cryptography and steganography, and its most obscure clues reference everything from Anglo-Saxon runes to occult philosophy. No one knows who’s behind the game – only that they’re “looking for highly intelligent individuals.”

Photo credit: Cicada 3301

The puzzles start online with an encrypted message that requires steganography software to decode, but the clues often lead to real-life locations in various countries around the world, including the US, Japan, and Poland. Players would find flyers with an image of a cicada pasted on telephone poles that contained instructions for the next step of the puzzle.

To solve them, one has to be mathematically minded and relentlessly persistent. While the answers to the mysteries of Cicada 3301 still evade many, this enigma has given rise to communities of hackers and crypto analysts, working collectively to beat the unbeatable.

2. Project Architeuthis

This recruitment campaign, disguised as an alternate reality game or ARG, was launched in 2014 to attract experienced cryptologists. Project Architeuthis was the United States Navy’s answer to Cicada 3301, but with a clear storyline. The adventure starts with the kidnapping of a Navy engineer. To save him, a cryptologist sneaks aboard the enemy’s submarine and sends a series of cryptic notes over 18 days to lead rescuers to their base.

Photo credit: Project Architeuthis

The quest ends with an email address provided with the final puzzle. The first 10 people to submit the right answers were identified by the Navy as “the next generation of cryptologists.” At the end of the project, the Navy managed to hire some of the identified candidates and meet its recruiting goals.

3. CyPhinx

Developed by the Cyber Security Challenge UK in 2015, CyPhinx is the first among three parts of the Cybersecurity Challenge Singapore. It takes the form of a 3D virtual skyscraper with four games on the Singapore floor: “The Enemy Within,” “Cyber-Tent,” “Whitehatters Webapp,” and “Pen-Ding.”

Each challenge mimics actual scenarios that cybersecurity professionals face, such as battling data leaks by insiders and devising a cyberincident response, which requires cyber forensic skills and knowledge in vulnerability assessment and network security. The aim of the game is to accumulate as many points as possible.

Photo credit: CyPhinx

The top 30 scorers will enter the face-to-face portion of the competition. Six finalists will then embark on a sponsored trip to London to compete in the Masterclass Final, in addition to winning prizes such as cybersecurity courses. CyPhinx is a stepping stone for those without relevant experience or academic qualifications to demonstrate their skills, allowing them to kickstart their career in cybersecurity.

Anyone can play CyPhinx, but the Cybersecurity Challenge Singapore is only open to the city-state’s citizens and permanent residents. Additionally, those who already work in the cybersecurity field aren’t eligible.

4. Can You Crack It

Another online code-breaking game used as an unorthodox recruitment tool is Can You Crack It. Unveiled by the Government Communications Headquarters (GCHQ), an intelligence and security organization that provides signals intelligence and information to the UK government and armed forces, it has been said to be technically more complex than Cicada 3301, but less time-consuming and more focused on cybersecurity skills relevant to the intelligence agency.

The three-stage challenge tests participants on their abilities in JavaScript programming and reverse engineering, among others.

Photo credit: Can You Crack It

Apart from this, GCHQ’s director also released a five-part Christmas puzzle in 2015 where the solution to each part of the puzzle unlocks the next. The first one, for instance, featured a grid and a series of numbers. Solving it revealed a QR code linked to the second puzzle.

5. The Codebreaker Challenge

Similarly, the US National Security Agency (NSA) has the Codebreaker Challenge. A yearly affair designed mainly for US students interested in cybersecurity, the game involves participants assuming the role of an NSA employee and bases its challenges on a specific scenario per installment.

Photo credit: National Security Agency

Some of the puzzles in the past expected players to analyze strange codes, overcome anti-reverse engineering techniques, and create software for specific functions. Though other online quests backed by government agencies promise career-advancing opportunities, the Codebreaker Challenge only offered a “small token” to the first 50 students to solve the puzzles in 2017.

Nevertheless, it lets participants flex their coding muscles in a fun way and get into the cybersecurity industry even without paper qualifications.


The qualifying period for the Cybersecurity Challenge Singapore ends on August 1, 2018. To participate, register an account with the prefix “SG” (e.g. SGJohnTan) and download CyPhinx.

This post 5 of the most challenging puzzle quests on the internet appeared first on Tech in Asia.

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Anith Gopal
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