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After I updated my reminders on iOS 13 to the new version and it broke syncing between everything (mainly the watch app not showing all my iCloud lists), it eventually sorted itself out after a few days and it's working as normal now.

I figured the upgrade process happening in the backend of iCloud just took awhile to resolve everything across devices.
 
I figured it was because the upgrade issue so when Catalina finally came out I figured it would fix it but it hasn’t. I’ve tried everything.
 
Same here: iMac, MBP, iPad, iPhone, and Watch all in sync at all times.You don't have a device signed into iCloud that you no longer use do you?
 
Same here: iMac, MBP, iPad, iPhone, and Watch all in sync at all times.You don't have a device signed into iCloud that you no longer use do you?

good thinking but no. I was able to resolve this issue by unpairing.....which is what I was trying to avoid.
Thanks!
 
Had a Calendar syncing issue, but iPhone Watch app > General > Reset > Reset Sync cleared it up.
 
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