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Works fine for me both ways (MBP -> iPhone, iPhone -> MBP). Are you logged into your same iCloud account on both devices?
 
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Well it's broken again. iPad <-> iPhone, iPhone <-> Mac, etc. Deleting the plist at Library -> Preferences, com.apple.coreservices.useractivityd.plist, didn't work this time. This seems to have all started after the most recent updates to MacOS and iOS. ☹️
 
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