Cipher methods Symbols
Wingdings 2 (Microsoft, 1995)
Wingdings 2 is the direct sequel to the original Wingdings font (1990), released by Microsoft starting with Windows 95. Like the first, it was designed by Charles Bigelow and Kris Holmes (Bigelow & Holmes studio, also behind Lucida) and belongs to the dingbat family: decorative pictograms (instead of letters) mapped onto printable ASCII codes.
Wingdings 2 stands out for its sets of pointing hands, approval checks, stars, frames and calligraphic ornaments absent from the first volume. Installed by default on Windows for years, it remains a typographic classic of the Microsoft Office ecosystem, still used to dress up presentations and formal documents.
How does the alphabet work?
The cipher relies on a monoalphabetic substitution: each cleartext ASCII character is replaced by the font’s glyph at the same code. Same mechanic as the Caesar cipher (~50 BC) — a 1↔1 table — except the “key” here is the typeface itself.
The table covers 26 letters + 10 digits + 4 punctuation marks (! ? . ,). Other ASCII codes return additional decorative glyphs (fancy circles, multi-pointed stars), not exposed on CipherChronicle to stay consistent with the rest of the catalogue.
Cryptographic strength: low. A letter always maps to the same pictogram, which makes frequency analysis trivial (E remains the most common glyph in English). Wingdings 2 is valued for its decorative look in Word documents or escape-room handouts.
Historical and modern usage
- Microsoft Word / PowerPoint — checks, pointing hands, section ornaments.
- Vintage branding — nod to Windows 95-2000 interfaces.
- Paper escape rooms — humorous coding of “administrative” messages.
- Pedagogy — a textbook example of typographic substitution.
Related variants
- Wingdings (1990) — see our entry, first volume.
- Wingdings 3 (1995) — see our entry, third volume (arrows).
- Webdings (1997) — see our entry, web version by Vincent Connare.
What are the weaknesses?
- Monoalphabetic substitution — frequency analysis is immediate.
- Public font — installed by default on every Windows for 25 years.
- No polyalphabetism — no key, just the table.
The 40 glyphs
