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I have a new Mac and I didn't use the Migration Assistant to move my data. I want to now transfer my old messages from my old Mac to my new Mac. It appears all the old messages are in buried in the old Mac's Library folder.

Is it possible to migrate and merge my old messages from my old Mac to my new Mac?

If so, how?

Note, I do (did) use iCloud iMessage on the old and new mac, but it doesn't appear all my old messages were downloaded from iCloud to my new Mac when I setup my new Mac and iCloud. I'm not sure that's even how it works.

  • Is messages enabled on both Macs in iCloud preferences? Also for how it works: support.apple.com/en-us/HT208532 – ankiiiiiii Jul 8 at 8:15
  • The old Mac had iCloud turned on, but now all I have is a copy of old Mac on a drive. I would like to transfer the data from the ~/Library... folder if possible. – Swisher Sweet Jul 13 at 20:55
  • Okay one more thing, do you use an iPhone too? Please turn on text messages forwarding in messages preferences on it, for newer mac too. apple.stackexchange.com/a/364221/313842 See this answer for messages location. – ankiiiiiii Jul 14 at 4:38
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I was able to retrieve my ~/Library/Messages folder from a backup and copy it to a new Parallels macOS VM under the my Home folder on that VM. When I logged into the VM, I saw all my old messages.

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    Please mark your answer as resolved. – howdytom Jul 15 at 17:03
  • ~/Library/Containers/com.apple.iChat/Data/Library/Messages I recommend checking this too if there happens some glitch. – ankiiiiiii Jul 15 at 17:29

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