It Started as a Small Annoyance
Our setup is simple: images and documents get made on a Windows device, and a bot on the Mac mini picks them up. But file names were all over the place, so the bot often got confused about which one was the latest. Picture a folder full of 「final」, 「final2」, and 「really final」.
A Small Experiment
Same folder, only the naming rule changed, one week each.
• Before: free-form names like 「final_cardnews_edited2.png」
• After: date_topic_version names like 「2026-09-22_cardnews_v2.png」
The request to the bot stayed identical: 「Find this week's latest card news and add it to the review list.」
Results (from our own team log, a very small sample)
• Latest-version mix-ups: from about 5 a week down to 1
• Times the bot asked us to clarify: noticeably fewer
• Times a person opened the folder to double-check: almost gone
The Surprise
With the date at the very front, sorting by name is sorting by time. The bot doesn't need any clever judgment, it just grabs the last file in the list. When we put the date at the end of the name instead, the improvement was much smaller. It wasn't about having a date, it was about where the date sat.
Try It Yourself
YYYY-MM-DD_topic_vNUMBER.extension
1. Write the rule in one line and put it in a README at the top of the folder.
2. Don't delete old files, move them to an archive folder.
3. Add the same one-line rule to the bot's instructions.
Before asking a bot to be smarter, name your files honestly.