In the US, there are typically two different types of networks a transaction can go through, a debit type, and a credit type. Most (but definitely not all) debit cards can also be processed as a credit transaction. There are specific rules and regulations around how each type of transaction, especially related to chargebacks/fraud. Once a debit transaction is complete, it can be incredibly difficult to dispute after the fact, while there are 60 days to dispute a fraudulent credit transaction. This means the processing fees for credit transactions are more expensive than for debit, and nearly always come out of the seller’s pocket, hence some retailers only accepting debit transactions.
Your average larger retailer uses a Point of Sale device that can handle both types of transactions, and generally saves money (both in processing fees and chargebacks) by hoping you will choose debit. This is also (usually) the only method you can request cash back, since the transfer is treated, essentially, like an ATM transaction. When you “skip the PIN”, your transaction is processed as a credit card. If your account doesn’t have that feature (like some payday debit cards and high riak accounts), it will be rejected.
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