Ian Livengood

@The X-Phile (Part 1) I don’t know what “easification” means in this context. That’s not a term we use. But I can take a stab at this. If you’re referring to the difficulty of say, the Midi, all the puzzles are supposed to be about the same level of difficulty. Of course, there’s always going to be something that plays harder, but every puzzle should feel like an early-week Daily crossword difficulty. The Daily gets progressively harder, starting on Monday, peaking in difficulty on Saturday. The Sunday puzzle is larger, but about the same difficulty as a Thursday. We’re not intentionally making puzzles easier. If you solve, say, a Saturday daily puzzle from 2026, it’s probably going to be easier than a Saturday daily puzzle from 1996. It’s not because the puzzle got easier, it’s just that the references in the clues and answers are more topical and top-of-mind for a solver than something from 30 years ago. continued ...

@The X-Phile Part 2 If this question is about how to make a crossword “easier” or “harder,” the difficulty can come from four different areas: (1) The clues, which I can slide in difficulty. If the answer is ROCK with the clue [Classic rock cover?], that’s a Saturday-level clue. If it’s [Scissors topper, in a game], that’s a Monday-level clue. (2) The answers. Proper nouns are harder in general as they are know-it-or-you-don’t. Easier puzzles should have more accessible vocabulary. (3) The grid shape. In general, the more “open” a crossword is, the harder it is for solvers. Larger swaths of letters are harder to solve. Insider crossword alert! When there’s a diagonal black square “staircase” running from the upper-right to lower-left, the puzzle will be easier than a staircase running from the upper-right to lower-left. The reason is because in the former example, a scrabbly letter like “J” can start both words. In the latter example, it’s harder to have a word end with a “J” and start with a “J” on the same square. (4) In general, a larger puzzle is “harder” because it takes longer to solve than a small puzzle. A 5x5 Mini will almost always be easier than a 15x15 daily.

@Adam Thanks! If I understand your question correctly, I like every Pips puzzle to have a single solution. Caveat: When there’s a 1x2 place for a single domino and, say, a ≠ region condition where the domino can be rotated and it’s still correct, that doesn’t count as multiple solutions. To me, a multiple solution means a completely different arrangement, if that makes sense. On some Hard Pips a little trial-and-error is sometimes necessary. If you’ve exhausted all available logic, sometimes it works to go down one of two potential solving paths. In the end, one path won’t work, which you’ll hopefully figure out using logic, so the second path is correct!

@Becky Go Gunners! The Times wanted to make an original logic puzzle for a long time. Logic puzzles — unlike the English-centric focus of many of our games — appeal to a wide audience and reach beyond non-native English speakers. So, there was a big, untapped audience for a game like Pips. Pips was born out of an internal “game jam” — essentially a hackathon for games. The early version was low-tech — paper and pen and physical dominos! Games are pitched, and a select few like Pips, make it through the multiple rounds of testing. It was originally pitched in 2024, went live in beta in Canada in early 2025, and was released globally in August, 2025. We’re always looking at new games, so stay tuned!

@Vaer (Part 1) Good questions! I make 2-3 Midi puzzles per week, and fill in the other 4-5 from contributors. A little background: The Daily crossword has an open submission policy — anyone can submit a puzzle. But that means we receive about 200 submissions/week, and it takes all seven editors to cull through the submission pile. Since I’m the only editor who works on the Midi, it’s simply not feasible for me to comb through 800+ submissions/month by myself from outside contributors. At the same time, it’s also unreasonable to expect I should make all Midis myself. Cluing and filling a grid (at least for me!) doesn’t take *that* long, but theme generation does. I spend a lot of time exploring possible themes, many of which don’t make it to the solver. It’s challenging to create themes that are fun, novel, and most importantly, accessible to new solvers. So, we settled on a happy medium of working with known contributors. We started with a small crew of 15 puzzlemakers spread over 13 bylines. These were constructors I knew from their daily puzzles, and all the constructors have fun ideas, write good clues and can fill a grid up to Midi standards. Every contributor has a certain specialty – expert clue writer, super creative ideas, amazing smooth grid filler, etc. Ideally, each constructor is good at everything, but it’s nice to have a variety. We’re starting to mix in new voices, too, which keeps things fresh for solvers. Continued ...

@PipLOVER Rodolfo makes all the Hards and half of the Mediums. I make the Easys and and the other half of Mediums. Harder Pips puzzles are exponentially harder to make than Easys. I **could** make them, but it’s fun to let Rodolfo cook! He’s so good, it’s like asking Picasso to paint a stick figure.

@Vaer (Part 2) Often, the contributor will have an idea for animation, but I’ll work with them to refine the idea. In parallel, I work with our art team to see what’s feasible. Because the Games app offers multiple color themes for solving, working with color is harder than it looks. A color that looks fine on the default solving mode looks different in dark mode. Curiously, red is the hardest color to render well across all solving formats.

@Jennifer Similar to the streaks, we’re focused on daily gameplay right now! Pips is unique because there are three new games a day vs. one. The something-for-everyone model is a more robust offering and hopefully gives you more than enough to solve per day.

@CLN Rodolfo is a legend. It’s not hyperbole to call him the world’s greatest logic puzzlemaker. Rodolfo sends me weekly batches of Hards, and each week has a different “theme.” One batch of Hard puzzles will be animals, the next equations, say. I like to spread those puzzles apart so everyday is a surprise and delight moment for solvers!

@Jackson I’m currently reading “The Great Bridge” by David McCollough. Fascinating stuff about the building of the Brooklyn Bridge! I’m reading about 5 pages per day before bed. Unclear what’s taken longer – the bridge itself or me reading it. Well, answer length is a big part of it. The default size for the Midi is 9x9, so I’m always on the lookout for fresh nine letter answers. Sometimes a Monday-level theme is nice, but isn’t suited for the Sunday canvas. Think of a 21x21 as a large Thursday, so if an idea works for a daily Thursday, it’ll probably work as a Sunday

@Tim Smith Usually, the tile set is random. I make Pips by hand, and when I’m done, I’ll shuffle the dominos together and then sort them randomly. However, especially for certain Hards, it’s helpful to give solvers an ordered set to help keep track of the dominos. Does that make sense?

@Jonathan Stay tuned! Right now we're focused on the daily gameplay.

@Chris S Thanks, Chris! Love the enthusiasm! 🍪 🍪 🍪