Best Way To Scan & Transcribe Family Letters

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Family letters give us a peek into someone’s life from THEIR perspective, so letters deserve a prominent place in our family history. Here’s my 3-step process for scanning family letters and making them easier to access.

Linda and Charlie DatingThe day before I got engaged, back in 1981, I sat on my bed with a pen and a piece of paper and tried to make sense of my thoughts by writing them out. I had been in turmoil for weeks after Charlie and I broke up. I knew he wanted to marry me, but I wasn’t sure he was THE ONE for me. But over the next couple of months I realized how much I really DID care for him. But that day I was still struggling with whether he was the “right” one, and how do you know for sure?

I already know the end of the story, of course—that we DID get married and it was one of the best decisions I’ve ever made! I thought I knew that story pretty well, but a few days ago as I was going through a box of memorabilia, I found that very paper. When I read it I could feel it along with my younger self—even though I knew the outcome. That didn’t surprise me that much, but what did surprise me were some details I had totally forgotten. As the saying goes: The dullest pencil is sharper than the sharpest memory. That’s the power of letters. You get to participate with someone in your family that maybe you’ve never met and you get to see life from their perspective.

Let me share my 3-step process for scanning family letters.

Step 1: Transcribe Handwritten Letters

Step 1 is optional, and that is to transcribe handwritten letters. I LOVE seeing the handwriting because it’s so unique to each person, so I definitely want a scan of the actual letter, but let me share three good reasons to also transcribe them:

  1. First it’s often easier for family members to read letters when they’ve been transcribed—especially if the handwriting isn’t very legible.
  2. Secondly, it allows me to quickly copy and paste information or quotes that I can use in other family history projects
  3. The third and most important reason is that it makes the letter searchable because NOW you have words that your computer can actually search. Transcription App

To transcribe a letter I record myself reading out loud and then use a website called to create the transcription. Temi has a free phone app which allows me to push a button to start a recording and to stop or pause a recording as I read the letter. I try to speak as clearly as possible without slurring the words together. When I’m done I name the recording and click a button to upload it to and in just a few minutes I have a transcript. And it’s cheap—only 10 cents a minute!

I always take the time to read through the transcript to correct any errors, because Temi uses AI—artificial intelligence—so that’s why it’s a lot cheaper than sites where an actual human also looks at the transcript, but as long as you read clearly you should get good results with only minor changes needed. Then you can download it as a text file or Word document or PDF.

Temi is English-only but other transcription sites work with other languages. Just type “transcription ai” and your language in a search field to find an online transcription service that will work for you.

Step 2: Scan The Letter

Step 2 is to scan the letter, and you can use whatever scanner you have. A standard flatbed scanner can scan the letter as one or more jpegs and some can also scan multiple pages as a single PDF, which is what I prefer. I like PDFs because they keep all the pages of the letter together in one tidy document, but individual JPEGs are fine as well, and JPEGS might actually match the original color of the letter a little better.

Step 3: Name The Files—Date First, Then Name Of Writer

Step 3 is to name each JPEG or PDF with the date first and then the name of the person who wrote the letter. My naming convention is to start with the year, then month, then day if it’s available, and finally the name of the person who wrote it. By starting with the date all letters from that family group will line up sequentially in the correct order. Of course you won’t always be lucky enough to find a date on the letter and the cancellation mark on the envelope may be impossible to read so do your best to figure out an approximate year or decade from the context of the letter. If that’s impossible put it into a “MISC-Date Unknown” folder and simply use the name of the person who wrote it and a sequence number as the file name.

So those are my three steps for scanning family letters. It takes a little bit of extra time to scan or transcribe letters but it’s worth it because they contain hidden nuggets of family stories just waiting to be discovered and enjoyed!

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