This doesn't return all messages unfortunately, and the way the algorithm works, it will return a few results at a time, forcing you to re-pull for more results. I wanted all the messages I had received from my dad, and it was impossible to do this way.
Oddly this doesn't always give results for me, for things I KNOW are in my messages. All my iMessage history is on-device (I don't use and will never use iCloud backup). Pretty disappointing :\
Yeah I don’t use iCloud either, but that method always worked for me, where it does fail for you?! What’s the scenario where it doesn’t return what you were looking for?
Oh it's just like some arbitrary limitation, like the search function only goes so far back, or something. No clue, I haven't narrowed down the exact factors that determine whether my search will get a result or not
Supposedly iMessage search is getting way better in iOS 17. Fingers crossed.