waypost: never have a file named asdf.png again

Your Downloads folder is where files go to die. IMG_3427.png, Untitled_document_final_v2.pdf, a hundred things you'll never find again. Waypost fixes that. Waypost reads folders of your choice, then renames, sorts, and tags dropped files based on what's actually inside. No more guessing. It runs entirely on your Mac with Apple Intelligence, so nothing ever hits the cloud. And since there's no server to feed, it's yours for a one-time $7 payment.

I built a macOS app on a 9½ hour flight after work because I was tired of files named "Screenshot 2026-07-18 at 5.02.14 PM.png"

My desktop had become a graveyard of "IMG_3461.png" and "Untitled document (17).txt." I knew none of them. Opening each one just to rename it was a chore I was never actually going to do.

So I stopped renaming files by hand and built something that would.

Waypost reads what's actually inside a file (text, scans, PDFs, images) and gives it a name that makes sense, sorts it into the right folder, and tags it. All using Apple Intelligence, running entirely on your Mac. No cloud, no upload. Your lease agreement, your tax docs, your half finished essay: none of it ever leaves your machine. Turn off WiFi and watch it keep working.

Trust was the harder problem than renaming ever was. So I built in the controls I'd actually want: a toggle for every file type, naming conventions, folder-specific configuration, and an ask before renaming mode that suggests a name and waits for your click before touching anything.

Swift for macOS. Next.js on Vercel for auth. Stripe for payments. $7, once, no subscription, because there's no server to keep paying for.

the way it reads inside the files instead of just guessing from filenames is such a thoughtful move, and keeping everything on-device with Apple Intelligence makes it feel like the tool actually respects your mess.