Insights · engagement

The crossword email, and whether a puzzle belongs in your programme

A puzzle in an inbox is a genuine novelty. It's also a real production cost, and it earns its place in a handful of programmes.

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Alex Gregoriades, operations director at Engage Commerce
Alex GregoriadesOperations director
31 August 2026 939 words5 minute read
In short · six parts

Puzzle emails get shared internally as a clever idea and rarely survive the content calendar. They're genuinely fun. They pull unusual engagement. They also take longer to build than three ordinary campaigns, and whether that trade is worth it comes down to three things.

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Three things have to be true first

Let's face it: most brands who fancy sending a puzzle shouldn't. The first condition is an audience with time and affection for the brand, which usually means a hobby, a trade or a long standing customer base instead of a general consumer list.

The second is a vocabulary. A crossword works when the answers are terms your customers know and outsiders don't, so it turns into a small test of belonging. Not a general knowledge quiz.

The third is somewhere for the answers to go. A puzzle with no reveal, no leaderboard and no reply route is decoration. That's the version most brands send.

Be honest about the production time

ElementWhere it livesEffort
The grid and cluesAn image, plus a text list for accessibilityMost of the work
Playing itA page on your site, not the emailA build, once
The revealA follow up email a few days laterSmall
The prize, if anyTerms, a draw and a winner announcedMore admin than you think

The email can't be the puzzle. Interactive elements render unpredictably across clients and nothing keyboard driven works reliably, so the email carries the image and the link. The page carries the game.

A picture of a grid shuts people out

  • Publish the clues as text in the email as well as in the image, so a screen reader can read them out
  • Give the puzzle page a real text version, not a bare canvas element
  • Don't lean on colour alone to signal anything in the grid
  • Make sure the reveal email reads fine for somebody who never played

That goes for every visual game format, spot the difference and anything built on an image map included. If the campaign can't be enjoyed without seeing the picture, a chunk of your list is getting an empty email.

Cheaper formats that pull the same engagement

One question with a genuinely surprising answer. A caption competition, a guess the product from a close up, a poll with two links. Every one of those pulls similar reply and click behaviour for a fraction of the build.

A smiling woman in a red blouse at a laptop with a bank card in her hand, colourful paper shopping bags standing around her on the table

Start with one of those. If it pulls replies, your audience has an appetite for play and a crossword becomes a reasonable annual project. If it doesn't, the puzzle would have failed more expensively.

Once a year, to the engaged segment, in a quiet week

This isn't a programme staple. It belongs in the week where nothing's launching and nobody's buying, sent to the segment most likely to enjoy being asked to do something. Not the whole list.

Judge it on replies and on the campaign after it, not on its own revenue, which will be close to nothing. A list that's just enjoyed something opens the next send. That's the return this format actually produces.

Try a single question first

Put one question with a real answer at the bottom of your next campaign and ask people to reply with a guess. It costs nothing. Within a day you'll know whether a puzzle is worth building.

If the replies come in, build the grid and keep it as an annual fixture. If they don't, spend the same time on something your list has already shown it wants, which the engagement data in your account will name for you.

Alex Gregoriades, operations director at Engage Commerce

Alex Gregoriades

Operations director at Engage Commerce, where he runs the accounts the writing comes out of.

Do interactive elements work inside email?

Inconsistently. Support varies by client and by version, and anything needing keyboard input is unreliable. The safe pattern is an image and a link in the email, with the interactive version on a page you control. Build it the other way round and you'll spend the week answering people whose grid never loaded.

Should a puzzle email have a prize?

It doesn't need one. A prize brings terms, a draw and admin that usually outweighs the benefit, so think hard before you add it. If you do run one, keep it small and keep it relevant. A big prize pulls in people who want the prize, not the product.

How do we make a puzzle accessible?

Publish the clues as text alongside the image, give the puzzle page a text based version, and don't let colour carry meaning on its own. If the campaign only works visually, part of your list gets an email with nothing in it. Worth sorting before you worry about the grid.

What is a realistic result from a puzzle campaign?

Replies, forwards and an unusually high click rate, with very little direct revenue. We won't promise you more than that. Its value turns up in how the next few sends to the same segment perform, which is how any play based campaign should be judged.

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End matter

Test the appetite before you build the grid

A crossword email is a real novelty in an inbox and a real cost to produce. It works for brands whose customers share a vocabulary and care about the subject, and it fails quietly everywhere else. Test with one question, keep the game on a page instead of in the email, make it readable for people who can't see the grid, and treat it as an annual event. Not a format.

Alex GregoriadesOperations director · Engage Commerce

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