Wingdings as a puzzle cipher — anyone used font-based encoding in puzzles?

[EmmaWingding]

Hi everyone! I'm Emma, a web apps developer with a soft spot for typography and Unicode, and I've been thinking about Wingdings as a puzzle element.

For those unfamiliar, Wingdings is that old Microsoft symbol font where typing ordinary letters renders as little symbols instead — which makes it a ready-made substitution cipher. Every letter maps to a symbol, so any solver with the font (or a mapping table) can decode it.

Its most famous puzzle-ish appearance is probably in Undertale, where W.D. Gaster's dialogue is written entirely in Wingdings — players had to decode it to uncover hidden lore.

So I'm curious: has anyone here used font-based ciphers in puzzle hunts, cryptograms, or puzzles of your own? What do you see as the pros and cons versus a traditional letter substitution? On one hand it's instantly solvable with the right tool; on the other, it can be a fun "aha" layer. Keen to hear your thoughts!

[kb83]

Somebody posted a symbol substitution crypt here a while back. I found it an order of magnitude more difficult than a letter substitution, I think because my brain is now well practiced in detecting patterns in letter-substitution codes, but has no practice in seeing strings of symbols as words. It almost feels as if there is less contrast between symbols than between English letters, but again that is probably a function of learning rather than underlying brain function. It reminded me of being in an ophthalmologist office getting my vision checked, and seeing the adult eye chart with the usual capital letters, and then they had one for pre-reader children with objects instead: circle, polygon, heart, apple? I found the children's chart much harder to look at and see the characters than the adult one, because it seemed as if there was far less contrast between the different symbols in the children's chart than there was among the letters.