AI for Genealogy: Teaching AI to Read Great-Aunt Mildred's Cursive

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:

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Transcript

You know that feeling when you find a box of old family letters in the attic, and your heart starts racing because you know there are stories in there. But, then you open the first envelope and it's all in Great Aunt Mildred's flowing cursive handwriting that looks like beautiful art, but might as well be hieroglyphics. Well, what if I told you that in the next 25 minutes I'm going to walk you through exactly how to photograph those documents for perfect AI transcription, which specific AI tools work best for different types of handwriting, and the exact prompts that will get you the most accurate results? We're going from, I can't read this, to, AI just transcribed my entire family history in one episode. Welcome back to Ancestors and Algorithms, where family history meets artificial intelligence. I'm your host, Brian, and this is episode 5, where we're about to turn Great Aunt Mildred's cursive from a brick wall into a breakthrough. Today we're delivering on last week's promise, a complete step-by-step guide to getting AI to read those impossible handwritten documents that have been gathering dust in your research files. We're talking old letters, diary entries, census records with terrible handwriting, and yes, Great Aunt Mildred's beautiful but mysterious cursive. By the end of this episode, you'll know exactly how to photograph documents for optimal AI results, which specific AI tools to use for different handwriting challenges, and the precise prompts that consistently deliver accurate transcriptions. This isn't just theory. This is your practical playbook for revolutionizing your document research. Before we even think about which AI tool to use, we need to talk about the foundation of successful handwriting recognition, getting the photograph right. Because here's the thing, AI is your research assistant, not your researcher. And, like any good assistant, it can only work with what you give it. Think of it this way, if you can't read the handwriting clearly in your photo, neither can AI. But here's the good news, AI actually needs less perfect conditions than you might think, as long as you follow some key principles. Let me walk you through my five-step photography protocol that genealogists are using to get consistently better AI transcription results. Step one, lighting. Natural, indirect light is your best friend. Position your document near a window, but not in direct sunlight. Direct sunlight creates harsh shadows and can wash out faded ink. If you're working in the evening, use two light sources, one on each side of a document, to eliminate shadows. Here's a pro tip I learned from a genealogist in our Facebook group. Use a white pillowcase or sheet as a diffuser if your only option is direct sunlight. Just hold it between the sun and your document. Step two is background. Your document needs to contrast sharply with its background. For most old documents, which are typically light colored or yellowed, use a dark background. A black folder, dark wood table, or even a dark towel works perfectly. For documents written on a dark paper or with very light ink, flip this. Use a white or light colored background. Step three is angle and distance. Hold your smartphone directly above the document, parallel to the surface. The sweet spot for distance is about 12 to 18 inches away, close enough to capture fine details, far enough to get the entire page without distortion. Most modern smartphones will autofocus perfectly at this distance. If you're using an older phone, tap the screen to focus on the text before taking the photo. Step four is stability. Camera shake is the enemy of clear text recognition. If you don't have a tripod, use the timer function on your phone. Set it for three seconds. Position the camera. Then let go before it takes the picture. Another Lean your arms against the edge of a table to create stability. Or ask someone to help hold the document flat while you photograph it. And finally, step five is resolution and format. Use your phone's highest resolution setting. More pixels mean AI can see finer details in the handwriting. Save photos at JPEG. It's the most universally compatible format for AI tools. Take multiple shots if the document is long, because it's better to have several clear photos of sections than one photo where the text is too small to read clearly. Let me tell you about the mistakes I see genealogists making that sabotage their AI transcription results. The glare mistake. Photographing through plastic sleeves. Always remove documents from protective sleeves before photographing if possible. The fold mistake, not flattening the document. Creases and folds create shadows that confuse AI. Use a piece of glass or clearer acrylic to gently flatten documents without damaging them. The angle mistake, taking photos at an angle instead of straight on. This creates perspective distortion that makes letters look different than they actually are. The "too far" mistake. Trying to capture too much in one photo. It's better to make multiple close-up photos than one distant shot where the text is tiny. Now that we've got the Photography Foundation right, let's talk about which AI tools work best for different types of handwriting challenges. Here's what I've learned after months of daily testing. Different AI tools have different strengths when it comes to handwriting recognition. It's not just about good or bad. It's about matching the right tool to the specific type of handwriting challenge you're facing. Let me break this down by handwriting type and use case so you know exactly which tool to reach for in different situations. When you're dealing with printed handwriting, think census enumerators, clerks filling out forms, or anyone who is writing for official... records. GEMiLLAPS GEMNI 2.5 Consistently delivers the highest accuracy rates. Here's why: GEMNI has been trained extensively on structured documents and understands the context of forms. It's particularly good at recognizing standard abbreviations used in genealogical documents. Access for that is free tiered through a Google account or Google One AI Premium is $20 a month for the Pro version. For personal correspondence and cursive writing like Great Ann Mildred's Letters, Claude Sonnet 4 is your best bet. Here's why this matters: Claude tends to be more conservative with uncertain readings, which is exactly what you want with cursive text where letter formation can be ambiguous. Access to Claude, you get a free tier with Daily Limits, or Claude Pro for $20 a month for unlimited access to advanced models. When you're dealing with really challenging documents, faded ink, water damage, or historical scripts like old German handwriting, Perplexity's real-time web connection becomes crucial. Here's why: Perplexity can research historical context while it's transcribing. If it encounters words or names it's unsure about, it can cross-reference historical records and naming patterns to make more educated guesses. Access to Perplexity is a generous free tier, or Perplexity Pro, which is $20 a month for advanced models and unlimited searches. Now, here's something brand new that many genealogists don't know about yet: Ancestry launched their AI-Transcript feature just this past month, and it's specifically designed for documents you're adding to your family tree. Currently, Access does require a World Explorer or World Deluxe Ancestry subscription, which is about $40 or $50 a month. It's currently in beta testing with gradual rollout. Full access is expected by December 2025. Here's how Ancestry's approach is different. Instead of being a standalone transcription tool, it's integrated directly into your family tree workflow. You upload images to your tree gallery, either to a specific ancestor's profile or your main gallery. After you add basic details like dates and locations, a transcribe button appears within about a minute. What makes Ancestry's tool special? First, it's built on their proven handwriting recognition technology—the same system that transcribed over 150 million records from the 1950 US Census in just nine days. Second, the transcriptions become searchable within your family tree and can be linked to multiple family members. Third, it's perfect for sharing family letters with relatives who can't read the original handwriting. But here's a reality check. Ancestry's AI works excellently on 19th and 20th century documents. Genealogists are reporting "surprising accuracy" on century-old family letters. But it struggles with colonial-era documents and archaic handwriting. One tester found that a 1769 will transcribed "two cases of drawers and his pewter bed pen" as "two cows of dinner and my cater butt pen." So like all our tools, verification is crucial. Now let's get into the exact prompts that will get you the most accurate results from each tool. This is where the magic happens—the specific prompts that consistently deliver accurate transcriptions. I've tested dozens of different prompts, variations, and these are the ones that work best for genealogical documents. The Claude Sonnet four prompt for cursive letters. This is the exact prompt I want you to copy and paste when using Claude for personal correspondence. Quote, You are an expert genealogist and paleographer specializing in historical handwriting. Please transcribe this handwritten document exactly as written, preserving original spelling, punctuation, and capitalization. For any unclear words, provide your best reading in square brackets with a question mark like this. After the transcription, list any words or phrases where you have low confidence. Note any abbreviations or unusual terms that might have historical significance. End quote. Why this prompt works? It establishes Claude's expertise context, asks for exact preservation of original text, provides a clear format for uncertain readings, and requests confidence levels, all crucial for genealogical accuracy. For structured documents like census records or certificates, use this prompt with Gemini 2.5. Quote, I need you to transcribe this official genealogical document. Extract all handwritten information exactly as written, including original spelling errors. Organize the transcription to match the document's structure. Mark uncertain readings as square brackets. Provide a confidence, provide a confidence percentage for your overall transcription, and flag any names or places that seem unusual. End quote. Why this prompt works? Gemini excels at understanding document structure, and this prompt leverages that strength while still maintaining genealogical standards for accuracy. When dealing with difficult handwriting, use this prompt with perplexity. Quote, Transcribe this handwritten genealogical document, preserving original spelling and format. For uncertain text, provide context-based suggestions in brackets. After transcription, research any unusual place names or surnames you identify to verify they're historically accurate for that time period. Note any historical context that might help interpret uncertain passages. End quote. Why this prompt works? This leverages perplexity's web research capabilities to verify uncertain readings against historical records. Now let's put this all together with a complete walkthrough. I'm going to walk you through transcribing a typical challenging family letter, the kind of cursive handwriting that stops most genealogists cold. Step one is your document assessment. Before you even pick up your camera, look at the document and ask yourself, What type of handwriting is this? Printed, cursive, mixed? What's the condition? Clear, faded, damaged? What's the historical context? A personal letter, official document, diary entry? This assessment determines which AI tool you'll use and which prompt template to start with. For our Great Aunt Mildred example, we're looking at Flowing cursive handwriting, reasonably good condition but with some faded areas, Personal letter from the 1940s. This points us toward Claude Sonnet 4 with a cursive letter prompt. Now step two is your photography setup. Following our five-step protocol, you first position near a window with indirect light. Place on a dark background for contrast. Hold phone 12 to 18 inches directly above. Use a timer to avoid camera shake. Take multiple angles if needed. Remember, if you can't read it clearly in the photo, neither can AI. Step three is your AI tool selection and initial transcription. Based on our assessment, we're using Claude Sonnet 4. Go to Claude. ai, start a new conversation, and paste our cursive letter prompt. Upload your photo and wait for the initial transcription. Don't expect perfection on the first try. This is just your starting point. Step four is verification and refinement. Here's where your genealogical knowledge becomes crucial. Look at the transcription and ask, Do the names make sense for your family? Are the places geographically logical? Do the dates align with what you know about family history? Are there words that seem completely out of context? Use follow-up prompts to clarify uncertain readings. Remember our golden rule, AI is your research assistant, not your researcher. You're the genealogist who makes the final decisions. Step five is cross-verification. It's optional, but recommended. For really important documents, try the same photo with a second AI tool. If Claude gives you uncertain readings, try perplexity to see if its web research capabilities can provide additional context for unclear names or places. Consistency across tools increase confidence. Disagreement between tools signals areas that need your careful attention. And finally, step six is documentation. Always save both the original photo and the A. I. transcription. In your genealogy software, note which A. I. tool you used and which readings you verified or corrected. Future researchers, including future you, will thank you for this documentation. Let me share the most common problems genealogists run into with A. I. transcription and how to solve them. One problem is the A. I. keeps misreading the same letter. A solution for this is to look for pattern consistency. If A. I. consistently reads N as U throughout the document, you can do a find and replace to fix all instances. This is especially common with faded handwriting where certain letter combinations become ambiguous. Another problem is A. I. transcribes nonsense words. The solution for this? This usually means the image quality isn't good enough or you're asking A. I. to transcribe text that's too damaged. Try re-photographing with better lighting or accept that some documents may need human-only transcription. last problem is that A. I. misses entire lines or sections. A solution for this is to break up the large documents into smaller sections. A. I. works better with focused areas rather than trying to process an entire page of dense handwriting at once. Now, here's a bonus tip. These same tools work for translation. If you have documents in foreign languages, use the transcription first, then ask the A. I. to translate the result. This two-step process often works better than trying to translate directly from the handwritten image. All right, here's your homework and I want everyone to try this complete workflow. Your mission? Find one handwritten document that you've been putting off transcribing. Follow our complete six-step process. Number one, document assessment. Identify the handwriting type and condition. Step two, photography. Use our five-step protocol for optimal images. Step three, A. I. tool selection. Match the right tool to your handwriting type. Four, initial transcription. Use the appropriate power prompt. Five, verification and refinement. Apply your genealogical knowledge. And finally, number six, documentation. Save everything for future reference. Now, share your results. Email me your before and afters, the original challenging document and the A. I. transcription results. I want to hear about your breakthroughs, your challenges, and yes, even your hilarious mistakes A. I. makes. Send an email to me at ancestorsandai at gmail.com Or, come join our Facebook group. Search for Ancestors and Algorithms AI for Genealogy. If you're feeling ambitious, try the two-tool method on your most important document and let me know how the results compare. Next week's episode is going to be a complete game changer. From family facts to family stories, using A. I. to write compelling narratives that make your relatives actually want to read about their ancestors. We're talking about taking those dry genealogy facts, birth dates, census records, military service, and turning them into stories that read like the best family novels. I'll show you the exact A. I. prompts that transform John Smith was born in 1847 and moved to California into compelling narratives that bring your ancestors to life. Remember our golden rule. AI is your research assistant, not your researcher. These tools are going to revolutionize how quickly you can transcribe handwritten documents, but your genealogical knowledge and verification skills are what make the results trustworthy and accurate. Until next time, keep exploring, keep questioning, and keep bringing those family stories to light, one transcribed letter at a time. This has been Ancestors and Algorithms. I'm your host Brian, reminding you that every handwritten document you successfully transcribe with A. I. brings you one step closer to understanding the real voices of your ancestors.