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Adding a photo to a synchronised folder doesn't start synchronising.
Closing Lightroom and starting starts synchronising or stop synchronsing the folder and start synchronising the folder starts sybchronising the photo.
I am refering to a folder in collections with a synchronise icon in front:
Stopping and starting synchronise from the cloud icon:
Also starts synchronising the photo.
Lightroom sync should stay on all the time, unless you actively turn it off. It can turn off if you're changing catalogs a lot as there's usually one main catalog that's connected. Once a photo is added to a collection, it should start to sync. It's not immediate as the Smart preview needs to generate and upload.
It works like it should now.
Perhaps the "Stopping and starting synchronise from the cloud icon" made it work automatically again.