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September 2, 2025 β€’ 20 mins

Teaching AI to Read Great-Aunt Mildred's Cursive: Step-by-Step AI Transcription Mastery

Tired of squinting at impossible-to-read family letters and handwritten documents? In this episode, I walk you through the complete process of getting AI to transcribe those challenging handwritten genealogy documents that have been gathering dust in your research files.

You'll learn the exact 5-step photography protocol that genealogists use to get consistently better AI results, which specific AI tools work best for different types of handwriting challenges, and the precise prompts that deliver the most accurate transcriptions.

What You'll Discover:

  • How to photograph documents for optimal AI transcription (lighting, angles, backgrounds)
  • Which AI tool to choose: Claude Sonnet 4 for cursive letters, Gemini 2.5 Pro for official documents, Perplexity for challenging historical scripts, or Ancestry's brand-new AI Transcript feature
  • Copy-paste ready prompts that consistently deliver accurate results
  • Step-by-step walkthrough of transcribing a typical challenging family letter
  • Pricing comparison of free vs. paid options ($20/month tools vs. Ancestry's premium integration)
  • How to verify AI results and avoid common transcription mistakes

Featured Tools:

  • Claude Sonnet 4 & Opus 4.1 (best for careful cursive transcription)
  • Google Gemini 2.5 Pro (highest accuracy for structured documents)
  • Perplexity AI (real-time research for challenging documents)
  • Ancestry's new AI Transcript feature (launched April 2025, perfect for family tree integration)
  • Transkribus, FamilySearch AI, and other specialized genealogy tools

Perfect For:

  • Genealogists struggling with illegible handwriting
  • Family historians with boxes of old letters and documents
  • Anyone wanting to preserve and share family stories
  • Researchers looking to save time on document transcription

Remember our Golden Rule: AI is your research assistant, not your researcher. These tools will revolutionize how quickly you can transcribe handwritten documents, but verification and genealogical judgment remain essential.

This Week's Homework: Try our complete 6-step transcription process on one of your challenging family documents and share your results with our community!

Next Episode Preview: Learn how to transform dry genealogy facts into compelling family narratives that make your relatives actually want to read about their ancestors.

Connect with Ancestors and Algorithms:

πŸ“§ Email: ancestorsandai@gmail.com
🌐 Website: https://ancestorsandai.com/
πŸ“˜ Facebook Group: Ancestors and Algorithms: AI for Genealogy - www.facebook.com/groups/ancestorsandalgorithms/

Golden Rule Reminder: AI is your research assistant, not your researcher.

Join our Facebook group to share your AI genealogy breakthroughs, ask questions, and connect with fellow family historians who are embracing the future of genealogy research!

New episodes every Tuesday. Subscribe so you never miss the latest AI tools and techniques for family history research.




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