I don’t know if this would be it. But when you go to your Location Services settings, scroll down and tap on the Find My app, what are the settings? If “Precise Location” is off, I wonder if there’s a lag in your phone’s location updating that causes your watch to think it’s separated.
Settings > Privacy > Location Services > System Services > Find My (ON).
The way System Services work is still a bit of a puzzle and can make things to stop working or work less reliably even if the toggle is enabled within another setting (i.e. Optimized Battery Charging).
Also, inside System Service make sure to have “Significant Locations” enabled. I don’t know why but having it enabled has made some stuff like alerts, notifications and location more reliable.
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