I've found that the auto-transit feature doesn't seem to work at readers that are looking for a 交通 FeLiCa chip -- this probably affects very few people here, but some KONAMI arcade machines don't seem to respond.
How long are you waiting before it responds? Is it instantaneous?
As soon the コンビニ reader/pad lights up, flick my wrist down and it responds within say a second or less ? Was the same for Book Off too.
No need to touch the side button at all.
The register peeps and just after the watch vibrates to confirm successful payment.