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So I think I wasn't wrong to recall that at some point, Message deletion did not sync to the Apple Watch. For instance, see this thread on Apple Discussion: https://discussions.apple.com/thread/252984890

However, it looks like with the latest iteration of WatchOS, message deletion with the exception of SMS text does sync delete across to Apple Watch! At least so far that seems to be the case for me.

Yes that's right. SMS deletion still doesn't sync
 
Little off topic but I'm having the opposite problem. iMessages on my Mac, once I delete DO NOT delete off my iPhone and yes I have the setting on and always have. It just started today.
 
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Little off topic but I'm having the opposite problem. iMessages on my Mac, once I delete DO NOT delete off my iPhone and yes I have the setting on and always have. It just started today.
ugh.

Various sync issues across iCloud occur from time to time, including for example, iCloud tabs not syncing.

Another example is I have NEVER been able to get Screen Time to properly show up. I have 3 devices in which Screen Time is applicable: laptop, phone, iPad. The iPad Screen Time never shows up on laptop or iPad but will show up on phone.
 
ugh.

Various sync issues across iCloud occur from time to time, including for example, iCloud tabs not syncing.

Another example is I have NEVER been able to get Screen Time to properly show up. I have 3 devices in which Screen Time is applicable: laptop, phone, iPad. The iPad Screen Time never shows up on laptop or iPad but will show up on phone.

Same here. Screen time across devices has never worked correctly for anybody that I can see since they released it. Truly gobsmacking how incompetent Apple are with these kind of services. They aren't fit for purpose.
 
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