I think that everyone with this problem could pay at the ticket machines using apple pay instead of card. I use apple pay every day both with my debit and credit cards, and I’ve never had any problem with the PIN, even if the amount paid is more than 25 euros.
Every trenitalia’s (and BLQ airport express bus, too) self service ticket machine is equipped with a contactless reader (that, for rail tickets, is located below the touch screen).
If you have a contactless credit/debit card and the amount paid is less than 25 euros, you can pay at the machines with your card. However, you must tap your card next to the reader (and not insert them)