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I don't use Message in iCloud. I just depend on my various devices catching and saving conversations, but I've never felt a super-urgent need to archive the messages. I do, however, set Messages > Preferences > General > Keep messages to Forever. I have lots of disk space.

However, I was surprised to find that the upgrade has apparently wiped out all of the conversations I'd had on Messages on my MBP. It looks like whatever it is storing currently will be saved, as it had in the past.

It also looks like the old chat database is still in my Library, in ~Library/Messages/chat.db.incompatible.v13004.sqlitedb, meaning that the chat file somehow has a different format now. I suppose I could dig into the old file with a database reader and extract the messages, if I felt the need. Or I could turn on Messages in iCloud on my iMac, let them upload, then see if they sync to my MBP.

(On a related note, the upgrade to iOS 13 seems to have wiped out my Health data, at least in the Health app, and my other apps don't seem to be able to feed data into Health like they did previously. As with Messages, I don't keep Health data in iCloud.)

-awlabrador
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