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Vivoactive 4 History Not syncing

Hello, 

I have searched through the forums and cannot find an answer for this question. 

If I use a non-garmin device to record a ride and then import that ride to Garmin connect web it will not sync with my vivoactive 4 watch and show in the history. I find this odd as if I ride on zwift those rides eventually show up on my watch's history even though I don't use my watch to record them. 

Am I missing some checkbox in the Garmin Connect Web app to upload them to my watch and show in the history?

I can provide more detail if needed.