No, you do not have to pay for a carry-on bag twice for a layover, provided both flights are part of the same booking and ticket. When you purchase a ticket in 2026 that includes a carry-on allowance, that allowance covers your entire journey from the origin to the final destination, regardless of how many stops you have. If you are flying a budget airline (like Spirit or Ryanair) where you must pay for a carry-on, the fee you pay during booking is for the "trip," not per individual leg of the flight. The only exception to this rule is if you have booked two separate tickets on different airlines (e.g., flying London to Paris on EasyJet and then Paris to Rome on Vueling). In that case, you are technically ending one trip and starting another, and you would have to pay each airline's respective baggage fees. For a standard connecting flight with a layover on one itinerary, your baggage fees (and boarding passes) are handled once at the start of your journey.