Basically it references the purchase to your history and if there's something funky it forces you to re-auth.
Mostly happens to me on vacations and road trips when I pay in multiple locations 100s of km away from each other.
But I've never had to do it at my local grocery store(s), even though I might visit them multiple times a week.
"In a ‘card present’ scenario, the convenience of contactless at point-of-sale would remain, however customers will be asked to complete a Chip and PIN transaction when they reach the maximum total contactless spend, or have exceeded the card issuer's limits for consecutive contactless transactions since they were last authenticated." [1]
"When you spend around £100 in shops (across multiple payments, not just in one go) without having used Chip & PIN , we’ll do an extra security check by declining the next contactless payment and asking you to use Chip & PIN instead. " [2]
[1] https://www.barclaycard.co.uk/business/business-matters/frau... [2] https://monzo.com/blog/2019/09/11/strong-customer-authentica...
It is pretty annoying because there are a lot of terminals that don't have the PIN keyboard, e.g. on vending machines. If you card decides it needs PIN, you are not buying, unless you can sidestep it using a phone.
It doesn't seem to be universal though. I paid for multiple hotels in Europe (so hundreds of pounds/Euros) with contactless payments and--although I actually made a point of making sure my card had a PIN after a problem on my previous trip--I never needed it.
Apple Pay does not force the above, as you have already identified yourself via mandatory biometrics or device PIN.