I've got three chip cards (two credit and one debit) linked to my Apple Wallet and I've never been prompted to insert a card.
Perhaps this is a merchant-level issue with their implementation?
The switchover to terminals supporting chipped cards, here in the US, has borne more than a passing resemblance to a dumpster fire. Even when you get it right, half the terminals make a very "
you've made a terrible error"-sounding beep when the transaction successfully completes - seemingly they're desperately worried you'll wander off without your card - and lots of the terminals
still have bits of cardboard stuck in the chip reading slot with
hand-scrawled notes saying "do not use". Really? The head office did that poor of a job of working through the use cases, and didn't envision at least the need for some mass-produced cards to block the slot? Could have had an industry-wide card with standardized graphics on it saying "
Sorry, not yet, keep sliding your card 
" in some quickly recognizable color scheme, and everyone would have quickly gotten used to seeing that and known what to do, and then the stores could just remove those helper cards when each system was fully switched over. But no, apparently
everyone involved/in-charge thought, "well one day the old terminals will be there, and then, overnight the magical faeries will sneak in and switch the terminals
and back-end systems over to the new system, and then the next morning the cashiers and customers will all know to use the new system in the new way." Really? That was your plan? Smh.
As it is, there's a handful of chains where I know that NFC works and I can just go ahead and use it, and in other places I have to ask "do your NFC readers work yet?" which, about half the time, gets the response, "what is NFC?"
Related: RiteAid switched, a while back, from their own store loyalty card to "Plenti", and spent great amounts of effort having their employees get everyone signed up for Plenti cards. Plenti has an iOS app. The Plenti iOS app will cheerfully help you put your Plenti card into Apple Wallet. There are still RiteAid cashiers, many months later, that get completely befuddled when they ask for my Plenti card and I show them my screen to scan. Nevertheless, its nice that I can complete the entire transaction there with
only my phone.
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Plus I don't have to make sure my credit card is charged overnight.
If your credit card does get charged overnight, check to see if maybe your cats are "borrowing" it to order cat toys and catnip on the internet.