Cipher methods Symbols
Webdings (Microsoft, 1997)
Webdings is a web dingbat font designed by Vincent Connare (the controversial creator of Comic Sans) and Sue Lightfoot for Microsoft, shipped with Windows 98 and Internet Explorer 4 in 1997. Thematic successor to Wingdings (see our entry), it differs through an explicit orientation toward the emerging web interfaces: eye, e-mail, phone, folder, printer, media player, and other standard UI icons.
Unlike Wingdings, which mixed religious symbols, zodiac signs and ambiguous pictograms (source of the 2001 conspiracy theories), Webdings uses only readable pictograms designed for the Web 1.0 context, when images were heavy to load and pictographic fonts offered a lightweight alternative.
The font has lost relevance with the rise of modern vector icons (Material Design, Font Awesome, Unicode emoji since 2010) but is still installed by default on Windows for backward compatibility.
How does the alphabet work?
The cipher uses a monoalphabetic substitution: every letter of the plaintext is replaced by a glyph drawn from a fixed correspondence table. It is one of the oldest cryptographic techniques on record — already described in antiquity (Caesar cipher, ~50 BC) — and the most directly readable family for a beginner.
The table holds 26 glyphs for the Latin letters, 10 digits and 4 punctuation marks (! . , ?). The glyphs are web-UI-oriented pictograms (eye, e-mail, folder, phone, printer, utility shapes).
Cryptographic strength: weak. Because every plaintext letter always maps to the same glyph, the cipher falls to a frequency analysis in a few dozen words (in both English and French, E remains the most common letter, an immediate entry point). Monoalphabetic substitutions are therefore used today for their decorative, playful or pedagogical value — not to protect real information.
Historical and modern usage
- Windows 98+ (1997-) — installed by default.
- Web 1.0 — UI pictograms on late-1990s sites.
- Pedagogy — studied in the history of web icon fonts.
- Backward compatibility — still present in Windows 11 to avoid breaking older documents.
Related variants
- Wingdings — see our entry, thematic predecessor.
- Font Awesome / Material Icons — modern vector successors of icon fonts.
What are the weaknesses?
- Monoalphabetic substitution — immediate frequency analysis.
- Documented alphabet — Microsoft’s official public table.
- Microsoft licence — proprietary font; the PNGs here are pedagogical reproductions.
The 26 glyphs
The 10 digits
The punctuation marks
