Sorting by date and filename — probably won't work
Sorting the Desktop or your screenshots folder by date in Finder can narrow things down in theory, as long as you actually remember roughly which week it was. In practice, "a few weeks ago" is already a fuzzy memory, and scrolling through a dozen screens of thumbnails, scanning by eye, isn't much faster than not sorting at all. Spotlight's search box matches filenames, but the default name macOS gives a screenshot is a timestamp — if you never renamed it, typing anything into that search box won't surface the one you want.
Preview's Live Text helps, but only so much
The Preview app on macOS lets you select text directly inside an open image, copy and paste it, even pop up a translation. That's genuinely useful, but it comes with a catch: you have to find and open the image first before it can help you select anything. It solves "how do I get this text out of the image I'm looking at" — not "which of these hundreds of screenshots has this text in it." In other words, Live Text helps after you've already found your target; it doesn't help you locate the target among a pile of screenshots.
What actually trips people up: content sticks, coordinates don't
Think it through and you'll notice that weeks later, what you remember tends to be fragments of content — "some error that mentioned a timeout," "that boarding pass," "the $24 charge" — not the date, the filename, or which folder it's in. None of the retrieval methods macOS offers (by filename, by date, by selecting text in an image you've already opened) actually matches on a fragment of content.
The usual outcome: ten minutes of scrolling, no luck, and you give up — either asking the person who sent it in the first place, or just retaking the shot if it's still possible. Either way, that stretch of digging was time spent for nothing, and you're not even guaranteed to get the original information back.
Search the text, not the filename
This is exactly the scenario on-device OCR search is built for. Shotbox reads the text inside a screenshot the moment you take it, and builds an index alongside the title it generates automatically. Weeks later, type "timeout," "boarding pass," or "24" into the search box, and it matches the actual text that appeared in the image — not a filename you made up after the fact. Once it's found, you get the original image, the recognized text, and the app it came from, all together.
One boundary worth stating plainly: this only covers screenshots you take through Shotbox's hotkey. Historical screenshots already scattered across your Desktop or other folders aren't part of this index — finding those still means falling back on the older methods above.
