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Family, Grandkids & Memories

Transcribe your grandparents' wartime letters

A Hacker News commenter says Claude and ChatGPT did an impressive job transcribing his collection of letters between his grandparents during World War II. He also notes that, at the time he tried, neither could keep pages in order and ChatGPT sometimes skipped a paragraph.

Tool used: Claude, ChatGPTAdded Oct 13, 2026

What they did

He has a personal collection of letters between his grandfather, who was fighting in Europe, and his grandmother in England, and used both AI tools to transcribe the handwriting.

How it went

He calls the transcription extremely impressive but says he hasn't worked on it in months, so newer versions may do better on page order.

Worth knowing

Upload one page at a time, compare each transcription with the original, and ask the AI to mark unreadable words rather than guess. Keep a list of names and places to check.

Try it yourself

Copy this into Claude (or any AI assistant). Replace the parts in [brackets] with your own details.

Transcribe this handwritten letter exactly as written, keeping the original spelling and line breaks. Mark any word you can't read as [unclear] and don't guess. After the transcription, list the people, places, and dates mentioned. This is page [number] of a letter dated [date, if known].

Source: Hacker News commenter MrSkelter, Hacker News, Dec 3, 2025. Read the original →

First-hand account by the person who did it. Summarized in our own words. Spotted a mistake or want this removed? Tell us.

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