Khan Engineering

Khan Engineering

We're the engineers behind Khan Academy. We're building a free, world-class education for anyone, anywhere.


Latest posts

Making Websites Work with Windows High Contrast Mode

Diedra Rater on March 21

Kotlin for Python developers

Aasmund Eldhuset on Nov 29, 2018

Using static analysis in Python, JavaScript and more to make your system safer

Kevin Dangoor on Jul 26, 2018

Kotlin on the server at Khan Academy

Colin Fuller on Jun 28, 2018

The Original Serverless Architecture is Still Here

Kevin Dangoor on May 31, 2018

What do software architects at Khan Academy do?

Kevin Dangoor on May 14, 2018

New data pipeline management platform at Khan Academy

Ragini Gupta on Apr 30, 2018

Untangling our Python Code

Carter J. Bastian on Apr 16, 2018

Slicker: A Tool for Moving Things in Python

Ben Kraft on Apr 2, 2018

The Great Python Refactor of 2017 And Also 2018

Craig Silverstein on Mar 19, 2018

Working Remotely

Scott Grant on Oct 2, 2017

Tips for giving your first code reviews

Hannah Blumberg on Sep 18, 2017

Let's Reduce! A Gentle Introduction to Javascript's Reduce Method

Josh Comeau on Jul 10, 2017

Creating Query Components with Apollo

Brian Genisio on Jun 12, 2017

Migrating to a Mobile Monorepo for React Native

Jared Forsyth on May 29, 2017

Memcached-Backed Content Infrastructure

Ben Kraft on May 15, 2017

Profiling App Engine Memcached

Ben Kraft on May 1, 2017

App Engine Flex Language Shootout

Amos Latteier on Apr 17, 2017

What's New in OSS at Khan Academy

Brian Genisio on Apr 3, 2017

Automating App Store Screenshots

Bryan Clark on Mar 27, 2017

It's Okay to Break Things: Reflections on Khan Academy's Healthy Hackathon

Kimerie Green on Mar 6, 2017

Interning at Khan Academy: from student to intern

Shadaj Laddad on Dec 12, 2016

Prototyping with Framer

Nick Breen on Oct 3, 2016

Evolving our content infrastructure

William Chargin on Sep 19, 2016

Building a Really, Really Small Android App

Charlie Marsh on Aug 22, 2016

A Case for Time Tracking: Data Driven Time-Management

Oliver Northwood on Aug 8, 2016

Time Management at Khan Academy

Several Authors on Jul 25, 2016

Hackathons Can Be Healthy

Tom Yedwab on Jul 11, 2016

Ensuring transaction-safety in Google App Engine

Craig Silverstein on Jun 27, 2016

The User Write Lock: an Alternative to Transactions for Google App Engine

Craig Silverstein on Jun 20, 2016

Khan Academy's Engineering Principles

Ben Kamens on Jun 6, 2016

Minimizing the length of regular expressions, in practice

Craig Silverstein on May 23, 2016

Introducing SwiftTweaks

Bryan Clark on May 9, 2016

The Autonomous Dumbledore

Evy Kassirer on Apr 25, 2016

Engineering career development at Khan Academy

Ben Eater on Apr 11, 2016

Inline CSS at Khan Academy: Aphrodite

Jamie Wong on Mar 29, 2016

Starting Android at Khan Academy

Ben Komalo on Feb 29, 2016

Automating Highly Similar Translations

Kevin Barabash on Feb 15, 2016

The weekly snippet-server: open-sourced

Craig Silverstein on Feb 1, 2016

Stories from our latest intern class

2015 Interns on Dec 21, 2015

Kanbanning the LearnStorm Dev Process

Kevin Dangoor on Dec 7, 2015

Forgo JS packaging? Not so fast

Craig Silverstein on Nov 23, 2015

Switching to Slack

Benjamin Pollack on Nov 9, 2015

Receiving feedback as an intern at Khan Academy

David Wang on Oct 26, 2015

Schrödinger's deploys no more: how we update translations

Chelsea Voss on Oct 12, 2015

i18nize-templates: Internationalization After the Fact

Craig Silverstein on Sep 28, 2015

Making thumbnails fast

William Chargin on Sep 14, 2015

Copy-pasting more than just text

Sam Lau on Aug 31, 2015

No cheating allowed!!

Phillip Lemons on Aug 17, 2015

Fun with slope fields, css and react

Marcos Ojeda on Aug 5, 2015

Khan Academy: a new employee's primer

Riley Shaw on Jul 20, 2015

How wooden puzzles can destroy dev teams

John Sullivan on Jul 6, 2015

Babel in Khan Academy's i18n Toolchain

Kevin Barabash on Jun 22, 2015

tota11y - an accessibility visualization toolkit

Jordan Scales on Jun 8, 2015


Minimizing the length of regular expressions, in practice

by Craig Silverstein on May 23, 2016

The problem

Software engineering interviews tend to be full of "algorithms" questions, because they're easy to explore in an hour, unlike the messy problems that most programmers deal with day-to-day: moving data from one place to another, error checking and recovery, etc. Most times when I do have to use a fancy algorithm, there's already a library to do it for me. But every so often I come across the need for a novel, non-trivial algorithm. This happened to me the other week, and the process of getting it to work was, I think, really interesting.

Here is the problem: we wanted to improve the way we serve Khan Academy urls by fetching our static urls (images, fonts, etc) from a different place than our dynamic urls (homepage, /exercises, etc). The way we would do this would be to give our CDN (the cache-friendly frontend that actually gets our urls are forwards them on to us) a regular expression that matches all our static urls. The CDN would know what to do based on whether the regexp matched the incoming url or not.

Here's the trick: our CDN limits the size of this url to 512 characters.

It would be nice if we could just have a url like ^/static/.*, but sadly our static urls are not organized in any way, and some of them are in third-party code, so it's not practical to just reorganize them.

It would also be nice if we could just have a regexp like .*\.(js|css|png|jpg|pdf), but sadly, we have some png files that are dynamically generated, and we have other dynamic routes that would match that regexp as well, such as /api/internal/ios/static_redirect/mobile-exercise-content-5.css.

So I had to do something more clever.

My assets

Google Appengine, which is the hosting platform we use, has you specify which resources are static files for its own purposes. You do this via a configuration file that has entries like this:

- url: /images
  static_dir: images

- url: /((fonts|khan-exercises|third_party)/.*\.eot)
  static_files: \1
  mime_type: application/
  upload: ((fonts|khan-exercises|third_party)/.*\.eot)

- url: /((fonts|khan-exercises|third_party)/.*\.woff)
  static_files: \1
  mime_type: application/
  upload: ((fonts|khan-exercises|third_party)/.*\.woff)

The first kind just says that urls of the form /images/* should be served by files on the local filesystem named images/*. The second kind is more complicated: images matching that input regexp should be served by files matching the static_files parameter. (\1 means: everything inside the outermost parenthesis of url.)

First solution: 402,025 characters long

The naive approach I tried first was to just use values of static_dir and static_files from the config file, match them against every file in our repository, and join them all together into a big regexp:


This regular expression was too big for our CDN.

It's also very fragile: we'd need to update the regexp in our CDN every time we added a new static file to our filesystem.

Second solution: 2,400 characters long

Next, I realized that the config file already listed regular expressions, so I could just concatenate those together instead:


This is a lot smaller than the above solution, and also more robust since we'd only need to change the CDN regexp any time we changed the config file, not every time we added a new file to our filesystem.

But it was still well over the 512 character limit.

Third solution: 824 characters long

My next thought was to take the url from the second solution, and "optimize" it. The problem of how to minimize a regular expression is actually well studied. Unfortunately, the studying is to show how hard it is. (PSPACE-complete, which is -- probably -- even harder than NP-complete.)

(There's also several well known results as to how to minimize the number of states in deterministic finite automata. But while DFAs are very closely related to regular expressions, minimizing the number of states in a DFA is not very related to minimizing the number of characters in a regular expression.)

But there are things you can do in practice to get a smaller regexp, even if not a minimal one, and it may be enough for your purposes. In this case, the biggest win seemed to be in combining shared prefixes, to end up with a url like:


I could not find any resources for how to combine shared prefixes in regular expressions, so I had to come up with an approach on my own. This was surprisingly difficult.

My first approach was to just sort the regexp patterns and then go through them one by one, keeping track of how much of the prefix of this url matched the next one. This worked in simple cases, but I could not figure out how to get it to do the right thing for nested parens like g(a(e_mini_profiler/|ndalf/)|enfiles/).

I gave up on that approach and eventually came around to an approach that just did one combine-step at a time. Given my list of regexps that I wanted to join together with |, I'd find the two that shared the longest prefix. (If there were multiple such pairs, I picked one arbitrarily.) I'd then combine those two to be <prefix>(<suffix1>|<suffix2>). I'd then repeat this algorithm again, but with one fewer regexp in my list than before. Eventually my "list" would have only one regexp in it, and I'd be done.

There were two wrinkles to this approach. Sometimes three or more regexps would share a longest prefix:


In that case, I'd combine all of them at once.

Second, I had to be careful of cases where the shared longest prefix was inside parentheses:


I didn't want to combine them to get ^/((fonts|khan-exercises(|third_party)/.*\.woff|)/.*\.svg)! That does not match what I want it to match. So I had to tokenize the regular expressions first, so that each parenthetical expression was considered a single "charcter".

Afer all this work, my regular expression had lots of nice parentheses in it, but was still 824 characters long.

Fourth solution: 208 characters long

This is where I had my big breakthrough. I realized my goal wasn't to find a regexp that matched all our static file urls, it was to find a regexp that distinguished our static-file urls from our dynamic urls.

This difference is subtle but important. For the second formulation we don't care what our regexp does with invalid Khan Academy urls, that is, urls that yield a 404. (In the first case, we'd have to make sure that all invalid KA urls were judged not-static.) After all, we don't care if our static-content provider or our dynamic-content provider is the one who gives the 404!

After this realization, I changed the way I thought about the static-file url regexps in our config file. I took each such regexp and shortened it to the shortest prefix that didn't match any of our dynamic urls (such as /videos/*).

This yielded a very minimal regexp: I could shorten, say, ^/genfiles/javascript/.*|^/genfiles/stylesheets/.* to just ^/ge. The result was well under 512 characters!

Fifth solution: 294 characters long

The fourth solution worked, but it was probably too minimal. If someone were to later add a dynamic route /get_id, say, to our website, the regexp-pattern ^/ge would cause the CDN would think that all /get_id urls were actually for a static file, and not forward them to the right place. This would cause confusion and trouble.

We could go through efforts to make sure everyone updated the CDN regular expression every time they added a dynamic route to our app, but that seemed like a lot of work and also error-prone.

So instead I made the prefixes a bit less minimal, by forcing them to end on a slash. So instead of taking the unique prefix ^/ge, we'd take the still-unique prefix ^genfiles/.

This increased the sizes of our regexp by almost 50%, but it's still well under 512 characters, and the robustness improvement makes it well worthwhile.

The big reveal

Are you curious what our final url was? Here it is. (I've broken it into multiple lines to make it a bit easier to read.)


Not the shortest url in the world -- there are some mini-optimizations that could make it even smaller, such as replacing ($|2$) with 2?$ -- but well within the 512-character limit, and pretty reasonable to read.

If you're interested in seeing how we got this, here is the source code. The bits to calculate the input routes are specific to Khan Academy, but the rest should be more generally useful.