The Lost Art of ITA Software Puzzles: When Problem-Solving Was Pure Joy

Today’s software engineering landscape is characterized by coding platforms like LeetCode, which filter candidates through a gauntlet of algorithmic exercises. But a little two decades ago, things were different. ITA Software, known for its revolutionary travel search technology, took a unique approach with its infamous “ITA puzzles.” These were not assessments or gateways for job applications but rather a way to signal that ITA was a company for those who loved complex, mind-bending problems.

The Era of ITA Puzzles (2004–2008)

The ITA puzzles appeared during a unique time in the tech industry—the post-dotcom bust, pre-startup boom period. Computer science enrollment was at an all-time low, and most engineering jobs lacked today’s perks. Companies that valued engineers were scarce, and job descriptions often resembled a certain well-known office comic. At ITA, though, they were different.

Why ITA Used Puzzles

The puzzles were a beacon, a way for ITA to say: “If you love solving problems, you belong here.” ITA’s puzzles were displayed in transit advertisements around Boston, tempting engineers who, even while commuting, couldn’t resist a good challenge. These puzzles weren’t required for hiring; they were just a means of attracting the kind of people who loved puzzles for their own sake.

What Set ITA’s Puzzles Apart from LeetCode

LeetCode and other coding platforms aim to filter candidates with algorithmic questions directly related to coding performance in technical interviews. ITA puzzles, on the other hand, served more as a cultural attractor. They were built to appeal to engineers’ curiosity, not as gates for applicants but as a form of intellectual invitation. You could attempt to solve a puzzle, get engrossed in it, and maybe—just maybe—end up considering ITA as a place to work.

The Famous Puzzles and Their Impact

1. Rebus

Rebus, one of the most popular puzzles, was not so much about coding as about conceptual thought and intellectual rigor. Engineers who tackled it often had it on their minds all day, a testament to the quality of puzzles that encouraged deep thinking, something that LeetCode challenges often lack.

Rebus Generator

A rebus is a phrase or sentence expressed partly or entirely through pictures. For this puzzle, you will use pictures from this archive to map pictures to associated words. Write a program that will take an English sentence (here’s a list of test cases for you to use) and generate a rebus from it. Here’s a simple example:

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That is, each word becomes a parenthesized expression with up to three components: a word corresponding to a picture from the clipart library, a sequence of letters to be added to the name of the picture, and a sequence of letters to be deleted from the name. Distinguish words used as pictures from other sequences of letters by prepending a colon. The order of letters must match: the letters to be added must be in the order in which they would appear in the target word, and the letters to be deleted must be in the order in which they appear in the image name. Your program should produce plain text output.

But there’s more to the puzzle than that. Suppose we charge 5 points for every consonant you add or delete, and 1 point for every vowel. Now come up with a rebus that costs the fewest points. The example above costs 57 points, but this rebus of the same phrase:

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costs only 31 points.

Finally, you can reduce the cost even further by adding or subtracting images (which cost nothing) instead of letters. If you use recursive encodings, you can get rid of letters altogether. For instance, a recursive rebus for “solve” is:

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Write a program to generate efficient, recursive rebuses with the lowest possible score. Balance performance with optimal scores as you see fit.

2. Add-a-Gram

This puzzle required participants to take a word and create a sequence of anagrams by adding one letter at a time. With each new word, a single letter was added to form a new anagram. This task wasn’t about the algorithm but about the cleverness and creativity to think beyond mere code.

3. Strawberry Fields

Strawberry Fields was an optimization puzzle, where engineers attempted to maximize a certain outcome given limited resources. Brute-forcing a solution was possible, but optimal solutions required insight, creativity, and an appreciation for mathematical elegance.

ITA’s Puzzle Philosophy

According to ITA cofounder Dave Baggett, these puzzles were meant to attract “curious and smart people.” They were not about hazing potential hires with grueling tests; rather, they were crafted to appeal to those who couldn’t resist a good intellectual challenge. This attracted engineers who thrived on the joy of problem-solving and valued mental rigor over the comfort of standard tools or established frameworks.

The Legacy of ITA Puzzles and Their Impact on Today’s Tech Scene

The spirit behind ITA’s puzzles contrasts sharply with today’s high-pressure technical assessments. Rather than being a “hiring gate,” they were a litmus test for passion, a quality that many early tech enthusiasts possessed. The ITA puzzles marked a time when problem-solving was as much an art as a skill—an era that laid the foundation for today’s coding platforms, but with a fundamentally different purpose.

ITA was later acquired by Google, and with it, the puzzles faded into tech lore. But they live on in the memories of those who fondly recall working on “Rebus” or “Sling Blade Runner” on their commutes, reminding us of a time when puzzles in tech were about passion, not performance filtering. For those who remember ITA’s puzzles, they weren’t hurdles but rather a calling card for a company where one could truly be an engineer—and an unabashed puzzle lover.

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