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I opened Messages on my MacBook Pro and clicked "Enable Messages in iCloud".

It said "downloading" (or something along those lines) for a good 10-15 minutes and then stopped, presumably done.

However, certain messages are clearly missing that are on my iPhone (I only text from my iPhone). I think mostly from the last couple of days, but there could be more I'm not sure.

Is that normal? Do iMessages from my iPhone only get uploaded to iCloud every few days or something?

I tried "Sync Now" and it didn't do anything

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I had this exact problem with my 14 inch M1 macbook pro 2021, and iphone 13, running the latest OSes as of Feb 2022. My iphone had all my messages, but macbook was missing messages from about the last day or so.


The way I solved it was to plug in (so that they are charging) both my macbook and iphone. Then, the macbook was still missing the messages. However, I then used my iphone and sent a single imessage to a family member (who also had iphone, so text message was blue) and instantly that message appeared on my macbook, along with all the missing messages from the past day.

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  • Messages.app on my Macbook is missing some months of messages and I tried the approach but in my case it didn't resolve the issue. There are a couple of alternative approaches described in the Apple Community but they seem rather laborious (1, 2). Commented Oct 19, 2022 at 14:08
  • Okay, the solution was much simpler. For some reason a couple of months ago my iPhone decided without notifying me to deactivate cloud synchronization for the Messages app. After reactivating (with power plugged in and connected to Wifi) the messages appeared on my Macbook. Commented Oct 19, 2022 at 14:30

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