How Far Away Are Computer-Generated Crosswords?

[Image courtesy of ESLTower.]

There’s no denying that computers play a large role in the world of crosswords today.

Some companies use computer programs to generate their unthemed crosswords, no human intervention necessary. Computer programs like Crossword Compiler aid constructors in puzzle design and grid fill, allowing them to build and cultivate databases of words with which to complete their grids.

And, of course, with those little computers in your pocket, you can solve all kinds of crosswords (like those in our Daily POP Crosswords and Penny Dell Crosswords apps).

Heck, computers are even getting pretty good at solving crosswords — just look at Matt Ginsberg’s evolving crossword program, “Dr. Fill.

An article in Smithsonian Magazine posed the question, “why haven’t computers replaced humans in crossword creation?”

The answer, as you’d expect, is simple: computers are just fine at plugging words into established grids and generating basic, unthemed crosswords.

But unthemed is the key word there.

When people think of The Los Angeles Times, The New York Times, The Chronicle of Higher Education, The American Values Club, The Crosswords Club, or any of the other well-respected crossword outlets in the market today, I doubt unthemed puzzles are what comes to mind.

And when it comes to creating themes, innovating, and playing with the conventions of crosswords in order to create puzzles that surprise and challenge solvers, computers simply don’t have the chops.

They might be able to solve puzzles, but as far as I can tell from my research, there’s no program out there capable of generating and executing a theme with any sort of wordplay element involved.

[Image courtesy of Crossword Compiler.]

There is an art to creating an exciting grid, an intriguing theme, or a new puzzle mechanic that solvers have never seen before. The creativity of constructors is truly boundless.

And, it seems, the potential for crossword grids is just as boundless.

Recently, Oliver Roeder of FiveThirtyEight challenged the puzzle fans in his readership to calculate how many different crossword puzzle grids were possible.

He offered the following conditions:

  • They are 15-by-15.
  • They are rotationally symmetric — that is, if you turn the grid upside down it appears exactly the same.
  • All the words — that is, all the horizontal and vertical sequences of white squares — must be at least three letters long. All the letters must appear in an “across” word and a “down” word.
  • The grid must be entirely connected — that is, there can be no “islands” of white squares separated from the rest by black squares.

Now, obviously, all of those rules can be violated for the sake of an interesting theme. We’ve seen grids with vertical symmetry, islands of white squares, and more. Heck, plenty of grids allow words to go beyond the grid itself, or allow multiple words to share puzzle squares.

[“Cutting Edge” by Evan Birnholz. A puzzle where answers extend
beyond the grid. Image courtesy of The Washington Post.]

But assuming these rules are standard, what total did solvers come up with?

None. They couldn’t find a total.

One solver managed to calculate that there were 40,575,832,476 valid 13-by-13 grids following the above conditions, but could not apply the same technique to 15-by-15 grids.

40 billion valid grids. For a comparison, there are 5,472,730,538 unique solutions for a 9×9 Sudoku grid, and I previously calculated it would take 800 years to use every possible 9×9 Sudoku grid.

Of course, that’s 40 billion 13-by-13 grids. The number of possible 15-by-15 grids must be orders of magnitude larger.

Consider this: There were 16,225 puzzles published in The New York Times before Will Shortz took over the NYT crossword. The current number of NYT crosswords in the XWordInfo database is somewhere in the neighborhood of 25,000 puzzles.

And they’re one of the oldest crossword outlets in the world. Even when you factor in the number of newspapers, magazines, subscription services, and independent outlets for crosswords there are these days, or have been in the past, we barely scratch the surface of a number like 40 billion.

Maybe by the time we’ve run through that many, AI constructors will have caught up.


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In Crossword Clue Parlance, it’s M, or K, or Grand

[Image courtesy of BikeNoob.com.]

A thousand of anything is a lot. Sure, the Proclaimers made it sound longer by mentioning 500 miles and then 500 more, but we’re still talking about 1000 miles there. That’s a lot of miles.

I wrote my first post for PuzzleNation Blog in August of 2012, nearly six and a half years ago.

This week, I uploaded my one-thousandth blog post on this site.

You might think after three posts a week for years, I’d be burned out. But it’s quite the opposite. I enjoy exploring the world of puzzles, delving into history, cracking the memes and riddles that go viral, interviewing all sorts of puzzle creators and fans, trying out new games and puzzles, talking about our awesome puzzle apps like Daily POP Crosswords and Wordventures

And sharing all of that with the PuzzleNation audience.

It’s a privilege, it really is. In many ways, I’ve become the voice of PuzzleNation, and I take that responsibility seriously. I try to both inform and entertain, and I’m constantly hunting for something new and unexpected to offer you.

[Image courtesy of Forbes.com.]

And speaking of you, the PuzzleNation readership, it kind of blows my mind how many different ways I get to interact with you.

I mean, first and foremost, there’s PuzzleNation Blog. Three times a week (and sometimes more), I meander up and down the seemingly endless avenues of the puzzle world and discuss them with you. What a treat.

And then there’s Facebook and Twitter, where I not only discuss all of our projects, but I can play games like the Crossword Clue Challenge every weekday and try to outwit you. (Spoiler alert: I rarely do.)

I also have opportunities to answer questions, share posts and information from fellow puzzlers, and engage with people one-on-one, something that feels increasingly elusive these days.

There’s Pinterest and Instagram, as well as in-person events like the American Crossword Puzzle Tournament and the Connecticut Festival of Indie Games.

And honestly, I want more of that. So let me ask you something, fellow PuzzleNationer…

What do you want to see from PuzzleNation Blog in 2019?

Is it brain teasers? Original puzzles for you to solve? Behind the scenes content about our apps? Tutorials on how to solve various puzzles? More interviews with constructors and other puzzle/game designers? More puzzle history? More reviews?

Comment below, or on social media, or even in person. Tell us what you want to see. Let’s make the most of this platform, shall we? =)

[Image courtesy of Bogoreducare.org.]

I’ve gotta say, it’s a little daunting to be celebrating one thousand blog posts with you.

I know some of you have been with us since practically the beginning, and I’m grateful. I know some of you have only recently started following us, and I’m happy to welcome you. Some of you I know by name, and many of you I don’t know at all — but I’m hoping to change that in the future.

In any case, thank you for your support, your enthusiasm, your ideas, your comments, your feedback, your shares and likes and clicks and hearts and thumbs up and app downloads and reviews and everything else we’ve shared. I look forward to many many more.


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You can also share your pictures with us on Instagram, friend us on Facebook, check us out on TwitterPinterest, and Tumblr, and explore the always-expanding library of PuzzleNation apps and games on our website!

Answers to our National Puzzle Day Starspell!

For National Puzzle Day (aka International Puzzle Day), we laid down the gauntlet for you, fellow puzzlers.

We challenged you to put your vocabulary skills and your word-forming knowhow to the test with a Starspell puzzle specially constructed for the holiday (as it featured all the letters in the phrase INTERNATIONAL PUZZLE DAY)..

The goal was to form common six-letter words by moving from letter to connected letter in the Starspell diagram. You were allowed to repeat letters, but only so long as you left the letter first and then came back to it.

We found 28 six-letter words. Did you find more than that?

Here’s our list: ALATED, ATONED, DEALER, DELETE, DENIED, DENOTE, DEPEND, EATERY, ELATED, EYELET, LAUREL, LENDED, LENDER, NEATEN, NEATER, NOTATE, PEALED, PENDED, REDEAL, RED-EYE, REINED, RELATE, RENDED, RENDER, REPEAL, REPEAT, TENDED, TENDER.

Did you find any that we missed? Let us know in the comments section below! We’d love to hear from you!


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It’s National Puzzle Day!

Hello hello, fellow puzzlers and PuzzleNationers! It’s National Puzzle Day (aka International Puzzle Day), and we hope you’re having a fabulous time!

As you might expect, we’re overjoyed to be celebrating this puzzliest of days with you, and we’ve got a few things going on today in honor of the holiday!

You can log into either the Penny Dell Crosswords App or the Daily POP Crosswords App for terrific deals, so be sure to check them out!

And that’s not all! We’ve got a marvelous little puzzle for you as well!


Today we’re testing your vocabulary skills and your Boggle mastery with a Starspell puzzle!

The goal is to form common six-letter words by moving from letter to connected letter in the Starspell diagram. A letter may be repeated in a word, but only after leaving it and coming back.

The letters in today’s puzzle, appropriately enough, all come from the phrase INTERNATIONAL PUZZLE DAY!

We found 28 six-letter words. How many can you find?

Good luck!

How are you celebrating National Puzzle Day, fellow puzzlers? Let us know in the comments below!


Thanks for visiting PuzzleNation Blog today! Be sure to sign up for our newsletter to stay up-to-date on everything PuzzleNation!

You can also share your pictures with us on Instagram, friend us on Facebook, check us out on TwitterPinterest, and Tumblr, and explore the always-expanding library of PuzzleNation apps and games on our website!

The PN Blog 2018 Countdown!

It’s one of the final blog posts of the year, so what do you say we revisit all of 2017 with a countdown of my ten favorite blog posts from the past year!


But before we get to the countdown, I want to briefly mention two interesting landmarks for the blog in 2018.

In January, we were cited as a source in a college term paper, which is pretty gratifying.

And in April, we were name-dropped in a CNET article about friend of the blog Hevesh5.

Okay, enough bragging. Let’s get to the countdown!


#10 Robot Invasion

With the rise of puzzle-solving programs like Dr. Fill and game-playing AIs like AlphaGo, we’ve been joking for years about machines trying to topple humanity from the top spot as Earth’s resident puzzle-solving masters.

But this year, it kinda stopped feeling like a joke. With Scrabble-playing robots, self-solving Rubik’s Cubes, and a computer program that might’ve cracked one of the most celebrated unsolved mysteries in puzzles, the machines might just be taking over.

#9 Crossword Fun

Crosswords are still the #1 paper puzzle in the world. With more than a hundred years of creativity, cluing challenge, and cunning construction behind them, they continue to fascinate and frustrate us. And we had a lot of fun with crossword topics this year in the blog. Two of my personal favorite entries were asking questions about common crossword clues and the post where we explored the brief-lived moral panic sparked by crosswords.

#8 Holiday Puzzly Gift Guide

Every year, one of my favorite activities is putting together our Holiday Puzzly Gift Guide. I get to include the best products sent to me for review by top puzzle and game companies, mix in some of my own favorites, and draw attention to terrific constructors, game designers, and friends of the blog, all in the hopes of introducing solvers (and families of solvers) to quality puzzles and games.

#7 Unsung Heroes

They say history is written by the victors, and that’s true in the short term. But in the long term, history belongs to truth, and more and more, unsung heroes are coming to the fore and getting the well-deserved recognition denied to them earlier.

This is true in the world of puzzles as well, and this year, we had the privilege of putting the spotlight on two iconic women from puzzle history that had previously been lost to time and revisionism: codebreaking visionary Elizebeth Smith Friedman and spymaster Alexandrine, the Countess of Taxis.

#6 Citizen Shoutout

Interacting with the puzzle community is one of the highlights of doing social media for PuzzleNation. And some of the most enjoyable blog posts from this year involved focusing on members of the community and giving them kudos for their contributions to PuzzleNation and the world of puzzles in general.

As such, we created our Citizen Shoutout series to honor those folks, and along the way, we’ve thanked game shops, local escape rooms, and dedicated solvers who make the puzzle community a better place.

#5 PNVR

April Fools Day pranks are an Internet tradition at this point. Some websites go all out in celebrating the holiday. (Heck, ThinkGeek has started using the holiday to tease the public’s interest level in “fake” products, going on to actually release some of those April Fools pranks as real items later in the year!)

So after last year’s Puzzles for Pets gag was a big hit, we couldn’t resist getting in on the pranking fun again this year. The result — PNVR, a fake virtual reality puzzling experience — was as layered as it was silly, complete with fake quotes, splash pages, photos of people riding bikes while playing, and more. The visuals were amazing and hilarious.

#4 Puzzle Events

There are few things better than spending time with fellow puzzlers and gamers, and we got to do a lot of that this year. Whether it was cheering on our fellow puzzlers at the American Crossword Puzzle Tournament or putting our hands dirty with some knock-down, drag-out, game-playing ferocity during our Tabletop Tournament, these interactions were both invigorating and encouraging. Events like these really help solidify the spirit of community that comes with being puzzly.

#3 International Puzzle Day Puzzle Hunt

And speaking of interacting with fellow puzzlers, for International Puzzle Day this year, we masterminded a little online puzzle hunt for PuzzleNation solvers. Involving clues hidden in both that day’s Daily POP Crosswords puzzle and Penny Dell Crosswords App free daily puzzle, solvers had to anagram and solve their way around the website in order to earn a prize. It was a serious challenge to design, and great fun to unleash on the world.

#2 Women in Crosswords and Roleplaying Games

Using the blog as an amplifier to get the word out about important causes and worthwhile projects is one of the best things about writing here. And this year in particular, we can be proud of doing our damnedest to vocalize the incredibly valuable role that women have played (and continue to play) in the puzzle/game community.

Whether it was discussing the gender disparity in published constructors in the major crossword venues or pulling back the curtain on misogynist gatekeeping in roleplaying games, we were privileged to ally ourselves with a brilliant, underappreciated contingent of the puzzle community.

#1 Wordventures

There’s nothing more exciting than getting to announce the launch of a product that has been months or years in the making, so picking #1 was a no-brainer for me. It had to be the announcement of Wordventures.

But it’s not just the app, it’s everything behind the app. I’ve watched it grow and evolve in development, and it’s truly unlike anything we’ve released before. The mix of music, imagery, storytelling, and puzzle-solving is so atmospheric and engaging.

It may sound self-serving or schlocky to talk about our flagship products as #1 in the countdown, but it’s something that we’re all extremely proud of, something that we’re constantly working to improve, because we want to make our apps the absolute best they can be for the PuzzleNation audience. That’s what you deserve.

And it’s part of the evolution of PuzzleNation and PN Blog. Even as we work to ensure our current products are the best they can be, we’re always looking ahead to what’s next, what’s on the horizon, what’s to come.

Thanks for spending 2018 with us, through robots and Rubik’s Cubes, through discoveries and daily delights, through puzzle launches and landmark moments. We’ll see you in 2019.


Thanks for visiting PuzzleNation Blog today! Be sure to sign up for our newsletter to stay up-to-date on everything PuzzleNation!

You can also share your pictures with us on Instagram, friend us on Facebook, check us out on TwitterPinterest, and Tumblr, and explore the always-expanding library of PuzzleNation apps and games on our website!

PuzzleNation Blog Looks Back on 2018!

2018 is quickly coming to a close, and as I look back on an eventful year in the world of puzzles and games, I’m incredibly proud of the contributions both PuzzleNation Blog and PuzzleNation made to the puzzle community as a whole.

Over the last year, we explored board games and card games, strategy games and trivia games, dice games and tile games, do-it-yourself puzzlers and pen-and-paper classics. We met game designers, constructors, artists, YouTubers, and creative types of all kinds.

We unraveled math puzzles and diabolical brain teasers. We pondered optical illusions, Internet memes, and more, even questioning our place in the world of puzzles as AI and solving robots continued to rise in capability.

We delved into puzzle history with posts about ancient board games from centuries ago, Edgar Allan Poe’s secret codes, and the legacy of influential female codebreakers and spymasters previously lost to revisionist history like Elizebeth Smith Friedman and the Countess Alexandrine. We brought to light valuable examples of puzzles in art, comic strips, animation, music, television, film, and popular culture.

We spread the word about numerous worthwhile Kickstarters and Indiegogo campaigns, watching as the puzzle/game renaissance continued to amaze and surprise us with innovative new ways to play and solve. We shared worthy causes like Queer Crosswords and Women of Letters, as well as amazing projects like new escape rooms, puzzle experiences like The Enigmatist, online puzzle quests, and long-running unsolved treasure hunts.

We celebrated International TableTop Day, offered up puzzly suggestions for Valentine’s Day, attended the American Crossword Puzzle Tournament, and dove deep into an ever-expanding litany of puzzle events like the Indie 500, BosWords, and Lollapuzzoola.

We found puzzly ways to celebrate everything from Halloween, Thanksgiving, and Christmas to Star Wars Day and the anniversary of the Crossword, and we were happy to share so many remarkable puzzly landmark moments with you.

It’s been both a pleasure and a privilege to explore the world of puzzles and games with you, my fellow puzzle lovers and PuzzleNationers. We marked six years of PuzzleNation Blog this year, I’m closing in on my 1000th blog post, and I’m more excited to write for you now than I was when I started.

And honestly, that’s just the blog. PuzzleNation’s good fortune, hard work, and accomplishments in 2018 went well beyond that.

Every month, we delivered quality content for both the Penny Dell Crosswords App and Daily POP Crosswords. Whether it was monthly deluxe sets and holiday bundles for PDCW or the world-class topical puzzles by some of the industry’s best constructors for Daily POP, hundreds of topnotch crosswords wended their way to our loyal and enthusiastic solvers.

And a little more than a week ago, we launched our newest puzzly endeavor — Wordventures: The Vampire Pirate — bringing you a unique, story-driven puzzling experience, complete with gorgeous visuals, atmospheric music, and an immersive mystery to keep you solving!

But whether we’re talking about crosswords, Sudoku, or Wordventures, I’m proud to say that every single puzzle represents our high standards of quality puzzle content crafted for solvers and PuzzleNationers.

And your response has been fantastic! Daily POP Crosswords is thriving, we’re very excited about the response to Wordventures, the blog has over 2300 followers, and with our audience on Facebook, Twitter, Instagram, and other platforms continuing to grow, the enthusiasm of the PuzzleNation readership is both humbling and very encouraging.

2018 was our most ambitious, most exciting, and most creatively fulfilling year to date, and the coming year promises to be even brighter.

Thank you for your support, your interest, and your feedback, PuzzleNationers. The new year looms large, and we look forward to seeing you in 2019!


Thanks for visiting PuzzleNation Blog today! Be sure to sign up for our newsletter to stay up-to-date on everything PuzzleNation!

You can also share your pictures with us on Instagram, friend us on Facebook, check us out on TwitterPinterest, and Tumblr, and explore the always-expanding library of PuzzleNation apps and games on our website!