Transcribe and date 150 old family letters for an archive with ChatGPT

Source checked Oct 30, 2026
Results shared

Copy the prompt below and paste it into the AI tool named on this page.

Prompt Recreated prompt

The source didn't share its exact prompt, so we wrote this from what it describes.

Transcribe this handwritten letter from the attached JPG. Keep the original line breaks, preserve the spelling exactly as written, flag any words you are unsure about and never invent missing text.

Try this in:

ChatGPT Used in source Gemini Grok

Sends the Recreated prompt shown above. ChatGPT and Grok open with it filled in, and ChatGPT may send it straight away. Gemini opens empty, so we copy the prompt for you to paste. Every button also copies it.

Opens in a new tab. We don't see what you send.

These links are only a shortcut. We're not affiliated with OpenAI, Google or xAI, and your results may not match the source.

Optional stronger version

Our rewrite with extra checks. The poster didn't test it.

Before you start, ask me 1–3 short questions about the details below and wait for my answers. Once I've answered, confirm the plan in one line and run the whole task start to finish.

Goal: Transcribe and organize a collection of old handwritten letters so they can be searched and dated.

Questions to ask me first:
- Roughly how many letters are there, and from what years?
- Who are the main writers and families?
- Do you need exact transcriptions, summaries or both?

Inputs (fill in or confirm):
- Scans of each letter (JPG or PDF): [SCANS]
- Known family names, places and dates: [FAMILY DETAILS]
- Any letters already dated: [DATED LETTERS]

Rules:
- Keep the original line breaks and spelling exactly as written.
- Flag any word you're unsure about, and never invent missing text.
- When suggesting a date for an undated letter, quote the clue in the letter and explain your reasoning.
- Keep a running index of people, places and events across all letters.

Checkpoint: Transcribe one letter and wait for me to check it against the original before continuing.

If you get stuck: If part of a page is unreadable, mark it [illegible] and move on.

Verify before you finish: Remind me to check each transcription against the original image and any dating clue against outside records.

Output: Transcriptions, a table of letters with suggested dates and clues, and an index of names and places.

Done when: Every letter is transcribed, checked and placed in likely date order.

AI tool

ChatGPT

Outcome

A co-chair of the California Genealogical Society's Manuscripts Committee scanned a collection of about 150 handwritten letters exchanged among Midwest family members and friends between about 1885 and 1925. The co-chair uploaded JPG images to ChatGPT with clear rules: keep the original line breaks, preserve the spelling exactly, flag unsure words and never invent missing text. The transcriptions weren't perfect but sped up the work, and every one was reviewed against the original letter. ChatGPT also explained references like Flinch cards and helped date undated letters, noting that Iowa was debating women's suffrage in 1919. Asked to find every letter mentioning an infant death, it showed some referred to an earlier loss around 1898, not the 1903 death the co-chair had assumed; genealogical records confirmed it.

Evidence: Described by posterThe person describes what happened in words, without screenshots or video.

Source

Posted: Mar 19, 2026 by California Genealogical Society blog (Manuscripts Committee co-chair)
Last checked: Oct 30, 2026
Method:: How we verify

https://www.californiaancestors.org/manuscripts/

Context: The post's author isn't named on the page. Dating clues from ChatGPT were confirmed against genealogical records.