Eight Years in, Messages on MacOS Still Sucks at Search annoying.technology

Manuel Grabowski (via Michael Tsai):

iMessage is eight years old. Never once in its entire existence has search on macOS (it’s such a long time that it wasn’t even called macOS back then!) worked properly. It is so ridiculously bad, there’s actually a third-party app that provides a functioning search. This total embarrassment of a situation is so old that said third-party app has been around long enough that I was still a student and too broke to buy the app back when I first heard of it. Instead, I built a poor man’s version myself – it’s just a simple SQLite database after all, nothing a few shell aliases couldn’t query quickly and efficiently. But apparently it’s still a problem too hard to solve for the almighty Apple.

There used to be a time where logs from what was then iChat were sensibly stored in ~/Documents/. I don’t remember whether iChat’s search was any good — the mere presence of Logorrhea suggests otherwise — but you could use Spotlight to search the folder and even preview chats with Quick Look.

In today’s MacOS, you can still search for message transcripts using Spotlight, but with several caveats. First, the transcripts are no longer in a user-friendly place like ~/Documents/, but are instead a couple of levels deep within ~/Library/. Second, while transcripts are named and categorized as you might expect — by chat participants and chronologically — attachments have an opaque organizational system. Third, SMS transcripts are not stored here; they only exist locally within a SQLite database. Fourth, you cannot use Quick Look to preview a transcript; and, fifth, when you open the transcript in Messages, it may be comprised of many days of discussion and will default to the most recent message, leaving you to scroll back and manually hunt for the chat in question. And, no, you cannot use ⌘-F in a chat preview window.

The search function within Messages itself is even worse. It is inaccurate, hard to use, and somehow incomplete.

Searching within iOS’ Messages app was a similar disaster for years, but it was radically overhauled in iOS 13. It’s not just better — it’s so great that it is hard to believe that both apps were created by the same company.