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Ok so where is this magic option to sync messages in iCloud? I went into Accounts according to their directions and there is no option 'Enable Messages in iCloud'?

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Seems it's all working (iCloud Messages). Some conversations are not on my phone but 98% are.

The new issue is, attachments are not all there. Large conversations have an empty bubble where the attachment should be. Some conversations have them, some do not. Some are SMS some are iMessage. No rhyme or reason.

Possibly still updating?
 
Ok so where is this magic option to sync messages in iCloud? I went into Accounts according to their directions and there is no option 'Enable Messages in iCloud'?

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Make sure you were actually successfully upgraded to 10.13.5. Mine went through the motions but wasn't upgraded on the first attempt.
 
For me, the update downloads and then says it needs to download more, rinse repeat. Will post more pics if this happens a 3rd time.
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I guess 3rd times a charm!
 
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Did you look at your iMessage account in the Message app itself? The setting is not in the iCloud preferences.

me neither. I checked both and nothing. Interestingly though Messages shows under iCloud preferences on my iOS devices but not on macOS. You'd think they would put it under iCloud instead same as iOS?
 
Only reason Apple created iCloud support for Messages is so users eat up their allotted storage even more quickly, thus motivating them/us to upgrade and hand over more $$$ to AAPL. $ad.
 
You know what the file system needs is a secure hash for each file data so that for example if two files were the same it would just keep one copy and point to that. I bet half the files on my system are duplicates of some other file somewhere else. Along with soft moves and copies that should seriously accelerate things like OS updates.
 
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