How to Solve Crossword Puzzles

5 Expert Crossword Solving Tips

After interrogating several crossword champions about the way they solve crossword puzzles so quickly and easily, I decided to summarize their answers in the form of a few easy-to-follow tips. This page was the result.

Check out Volume 1 of Word Buff's 'Totally Unfair' Word Game Guides!

As always seems to happen with me, things started to get a bit longer than I initially planned, so here is a quick list of links to the tips that might save your scrolling finger a bit of pain...

Throughout the article I use the popular convention...

[Clue] = ANSWER

to represent a clue/answer pair.

How to Solve Crossword Puzzles #1

Select the Right Crossword Puzzles

The first step to improving your crossword solving skills is to choose the right crossword puzzles to practice on! That means choosing puzzles that are well made and of the right difficulty level for you. Let's break that down...

How to recognize well-made crossword puzzles

Crossword making is an art form, and very few people are really good at it. This isn't the right place to get into the ins and outs of crossword construction, but let me give you an example of a useful sign-post.

Crosswords often make use of very obscure words or facts that hardly anybody is likely to know. Such entries are often referred to as crosswordese, and looked upon by most as a necessary evil. One tell-tale sign of a good crossword puzzle is that it uses minimal crosswordese, and that when it does resort to a really obscure word, the crossing entries (i.e. the words that pass through the obscure word) are not equally obscure.

There are many other signs of a good crossword puzzle of course, but an easier way to decide is to simply stick with crosswords having a reliable pedigree. By that, I mean crossword puzzles that are made by a respected constructor (or at least edited by a highly-regarded editor) and published in a quality publication or website.

Which ones are they? Ask the experts! A very comprehensive list of crossword puzzles with that kind of pedigree was very generously compiled for Word-Buff by the crossword solving champion, Dan Feyer.

How to get the right difficulty-level

Fortunately, many crossword publications provide some indicator of the level of difficulty of their puzzles. Some, like Brendan Emmet Quigley, give an explicit difficulty tag (in his case: Easy, Medium, or Hard), while others, most notably the New York Times crossword, use the day-of-the-week to measure difficulty. In New York Times puzzles, for example, Monday puzzles are the easiest and Saturday's are the hardest.

You need to start with a level of difficulty that matches your current ability, and work your way upwards. It's best to start with crossword puzzles that you can almost solve completely, but not quite. That way you'll learn something new with each puzzle, without shattering your confidence.

Rather than than wait for Saturday's challenge, crossword solving whiz Dan Feyer recommends increasing the difficulty of an early-in-the-week puzzle by solving only the Across clues or Down clues, or by only solving clues for which no letters have yet been filled in.

How to Solve Crossword Puzzles #2

Become Familiar with Cluing Conventions

Professional crossword editors adopt cluing conventions that they adhere to religiously. These conventions are crucial aids to solving crosswords, so you should familiarize yourself with them right away.

Below are some examples of the less obvious cluing practices used in the New York Times crossword puzzle. Many other crossword publishers follow very similar conventions...

  • A clue and its answer must always agree in every grammatical sense (i.e. number, tense, and so on). A good way to check for clue/answer agreement is described in a brief article, The Substitution Test, that I put together for the Word-Buff Stuff Newsletter.

  • If a clue contains an abbreviation, the answer is usually also an abbreviation. This is a more crafty way of signifying an abbreviation than the explicit "abbr." tag, which is also used sometimes.

    [Compass pt.] = ENE

  • If a clue uses a foreign word, person, or place, the answer is often from the same language or place. Again, this makes things a bit more interesting than using explicit tags, like "Fr." or "L.".

    [The end for Socrates] = OMEGA

  • If a clue is enclosed in quotation marks, it means the clue should be interpreted as something uttered rather than as a meaning.

    ["Heavens to Betsy!"] = EGAD

  • When an answer needs a modifier to match the clue strictly, the modifier is usually included in parentheses at the end of the clue, or after the word "with".

    [Bungle, with "up"] = MESS

  • If a clue ends in a question mark (not counting quotes that happen to be questions), the answer involves something devious and often chuckle-worthy.

    [Bolt without threads?] = STREAK

  • In a theme crossword, the theme entries are usually the longest ones, and are usually placed symmetrically throughout the grid.

  • The answer to a clue is never included in the clue itself.

Note that this crossword solving tip is only useful for solving good quality crossword puzzles in which the editor rigorously enforces cluing conventions. Yet another reason to follow Tip #1.

How to Solve Crossword Puzzles #3

Learn the Repeaters

A repeater is a crossword entry that tends to appear frequently due to its 'grid friendly' letter pattern. Some repeaters are obscure words — like ETUI, a French sewing case — that not many people are likely to know before seeing them in crosswords. As mentioned above, these repeaters are often referred to as crosswordese, and the sooner you get your head around them the better.

Other repeaters are common words, but to keep things interesting, they are often clued in obscure ways, like...

[Cost] = ARE

as in, 'These potatoes are/cost $4'. It's worth familiarizing yourself with these as soon as possible too.

Although you'll absorb the repeaters eventually through osmosis, the more impatient among us can get there faster through explicit study. I've put together some starter lists for you in the crosswords section of my word lists page. Beyond this, I thoroughly recommend Kevin McCann's 21st Century Crossword Puzzle Dictionary. It focuses on words and phrases that are most likely to appear in real crosswords and highlights the very high frequency answers. I've reviewed this crossword puzzle dictionary here.

How to Solve Crossword Puzzles #4

Work on Your Mental Game

When I interviewed five time champion crossword solver, Tyler Hinman, the youngest ever winner of the American Crossword Puzzle Tournament, I was intrigued by how much he emphasized certain psychological aspects of crossword solving. Here are some of his tips transcribed here verbatim...

  • Keep an open mind.

    If a clue's not budging, maybe you need to look at it differently. Could it be a verb when you've been thinking of it as a noun, perhaps? Be mindful of the different ways a short series of words can be read.

  • Be prepared to erase wrong answers.

    If you have a wrong letter and you assume it's right, it can really throw you off. If you're having trouble in an area where you have a few answers, revisit them and ask yourself if you're sure about them.

  • Keep staring at the damn thing.

    If you think the answer is gettable, odds are you're right. Sometimes your brain just suddenly breaks through with no warning.

  • If you're still stuck, leave, do something non-intellectual, and come back.

    The break can do wonders. (Not recommended in tournaments unless you're on stage and want to do something to break the boredom of the people who have been staring at your backside for ten minutes.)

How to Solve Crossword Puzzles #5

Use Crossword Solving Resources

When you just can't solve a clue, use one of the many excellent crossword puzzle solver resources out there to find out the answer. When you find the answer, don't just memorize it, learn more about it so you can anticipate other ways it might be clued.

Here are some of the clue solving resources recommended by the champion crossword solvers I've interviewed here at Word-Buff...

  • is a multifaceted word-finder that lets you search a collection of databases by word meanings or by word patterns. is an excellent free online crossword solver that finds all answers from the clue and word pattern you supply, and even explains how it interpreted the clue you entered!

  • SoftwareWordWeb Pro is a wordsmith's dream desktop application in my book. You can use it as a dictionary to look up obscure words, a thesaurus to find synonyms, or as a word finder for pattern searches, when you already know some of the letters in a clue. I've raved about this one elsewhere at Word-Buff.

    CrosswordMaestro is an application designed by an artificial intelligence expert to solve even the most cryptic crossword clues. This tool is fantastic for solving cryptic crosswords, but it's not so hot when it comes to solving straight (American-style) crosswords. This one isn't free (although it's not expensive), so don't part with the cash unless you're a fan of cryptics.

  • Dictionaries — As I mentioned in one of the earlier tips, the best dictionary on the market for solving crossword puzzles is Kevin McCann's 21st Century Crossword Puzzle Dictionary.

Recommended Books On
How to Solve Crossword Puzzles

These tips have been pretty broad, since covering the micro-details of crossword solving could itself fill an entire book. And speaking of books...

If you're after a book that does go into the real mechanics of crossword solving, I think you'd be hard-pressed to beat Matt Gaffney's Complete Idiot's Guide to Crossword Puzzles and Amy Reynaldo's How to Conquer the New York Times Crossword Puzzle.

These authors, who are both respected crossword constructors, explain how to solve crossword puzzles using different teaching strategies. Matt gives a very systematic 'no stone left unturned' analysis of the crossword solving process, while Amy proceeds in case-study style, patiently working through a crossword in front of us, explaining her thinking along the way.

The only thing you'll need once you've got those books on your shelf is practice!

For more tips like these, just take a moment to subscribe to my Word Buff Stuff! newsletter...

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