AMEX’s official website includes an explanation of the Shop Small offer; the full PDF is here.

First, here’s an awkward situation many people run into: because these are small merchants, you may find a merchant on the list, but they still tell you that their store does not accept AMEX credit cards.

Also, AMEX’s official terms specifically mention QUALIFYING PURCHASES and give a few examples of purchases that do not count:

For example, you may not receive the statement credit if (a) the Merchant uses a third-party to sell their products or services except that qualifying purchases made through Resy.com and the Resy mobile app will qualify for the offer; or (b) the Merchant uses a third-party to process or submit your transaction to us (e.g., using mobile or wireless card readers); or (c) you choose to make a purchase using a third-party payment account or make a purchase using a mobile or digital wallet.

Here’s a quick explanation:

  • The first situation means purchases made through a third-party platform for services do not count. This is easy to understand, such as food delivery platforms.
  • The second situation means payments made through a third-party payment terminal do not count. This may be fairly common, for example when many small merchants use card readers like Square or PayPal Here, hand-held swipers, iPads, or third-party large terminals. That will not work. Be sure to ask the store before paying so you do not get clawed back later.
  • The third situation means purchases made through mobile wallets or third-party wallets. At the moment it is unclear whether Apple Pay counts (Apple Pay has always worked fine with AMEX offers).But to be safe, it is still best to avoid it if possible.According to reader ameccy’s test, using Apple Pay directly is indeed fine, and using Apple Pay is much faster than tapping your card multiple times. If you are worried, you can try one small purchase first; once you receive the AMEX offer activation notification, you can keep using it.【Note: third-party card readers + Apple Pay are not allowed either】

The main issue, and the one most easily overlooked, is small merchants using third-party card readers. Third-party card readers usually charge a flat processing fee, and there may be discounts for higher volume. In my experience, many small merchants use Square and similar services (including third-party card readers that support Apple Pay). The settlement statement will show something like “Square*Merchant,” and these purchases will not trigger the Shop Small offer. That said, merchants definitely have AMEX card terminals on hand; whether they use them is another matter, since AMEX’s processing fees are just too high.

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