How to Handle Perplexing Crossword Clues That Feel Like Cheating
Let me walk through a specific category of clues that tripped me up for years, and why they work the way they do. The key is understanding that crossword constructors play by a different set of rules than you might expect. They're not trying to trick you out of malice. They're solving a puzzle within a puzzle, and the outer layer is just the grid. I encountered this exact phrase while working on a Saturday-level NYT puzzle. The clue was "Perpetrating" and the answer turned out to be something completely unrelated to what the word actually means. I nearly pulled my hair out. My initial instinct was to check whether I had the spelling wrong, or whether my dictionary app had crashed. Neither was the case. The actual mechanism at play here is something constructors call a double-definition clue with a misdirection component. In cryptic crosswords, this is standard fare. In American-style puzzles, it's rarer but still appears, especially in themed weeks. The clue "perpetrating" doesn't ask for a synonym of that word. It asks for a word that can itself perpetrate something. The answer ended up being a much shorter word hiding in plain sight.
Here's the workflow I developed after burning through three puzzles that week: Step one: Ignore the surface meaning entirely. When a clue feels like it doesn't match any definition you've ever seen, the first assumption should not be "I don't know this word." The first assumption should be "this is a wordplay clue." Count how many letters the answer needs. If the grid slot has six letters and the clue is eight words long, you are almost certainly looking at a cryptic-style construction, even in an American puzzle. Step two: Check for hidden words. This is the most common technique. Read the clue as a continuous string of letters and look for a word embedded inside it. For example, the word "perpetrating" contains "petting" which is five letters. It also contains "rater" and "ting" and other fragments. I once solved a clue where the answer was literally "per" hidden inside a much longer word in the clue itself. The clue read like nonsense until you spotted the substring.
Step three: Consider reversal and anagram indicators. Words like "reversed," "back," "confused," "wild," and "broken" are all anagram indicators in the constructor lexicon. If you see "perpetrating" followed by a long scramble of letters, treat the whole thing as an anagram instruction. I spent twenty minutes on one puzzle trying to find a definition match before I noticed the word "chaotic" at the end. That was the anagram indicator. The answer was a simple rearrangement of the earlier letters. One practical edge case that catches everyone: partial anagrams with a filler word. The clue might contain extra letters that aren't part of the answer at all. Constructors call these "padding words" and they're often prepositions or articles that feel grammatically necessary. I remember one specific puzzle where the clue was "Perpetrating a crime when wild about money" and the answer was just "MURDERER" after anagramming the letters of "a crime when wild." The word "about money" was the anagram indicator disguised as a phrase. It took me two re-reads and a cup of cold coffee to catch it. Another counter-intuitive insight: not every long clue is a cryptic. Some fillers in American puzzles are just thematic padding. The Chicago Tribune tends to use longer, more conversational clue templates that still have straightforward answers. If you're stumped, check which publication you're working on. LA Times clues tend to be more pun-heavy. Wall Street Journal clues lean toward the academic side. The Daily News version often uses straightforward synonym swaps that confuse people who overthink them.
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The hard truth about this category: it doesn't scale well for speed solving. If you're racing against a timer or filling in a quick Friday puzzle, spending four minutes hunting for hidden words inside a single clue will tank your completion time. I stopped trying to decode every unconventional clue after I realized I was losing more time than I gained. My current approach is to mark the uncertain ones, fill in the rest of the grid, and return with fresh eyes. Eighty percent of the time, crossing letters from adjacent answers make the solution obvious without any further analysis. When it absolutely fails: themeless Tuesday clues with genuinely obscure vocabulary. Sometimes the answer really is just a word you need to know. "Perpetrating" as a standalone clue in a non-cryptic puzzle genuinely means "committing." If your crosswords are solid, go with the straightforward definition. There's no shame in taking the easy read when the puzzle context suggests it. For those looking to practice, I recommend working through archived USA Today crossword collections from 2018 to 2022. That period had a noticeable uptick in misdirection-heavy clues, which gives you a solid training ground. Avoid the themed weekend editions for practice. They overload on gimmicks that don't appear in regular puzzles.
