In 2026, for standard domestic connecting flights on Southwest Airlines, you do not need to check in twice. When you complete your initial check-in (usually 24 hours before your first leg), you are checked in for all flights listed under that single confirmation number. Your boarding position (e.g., A16) is assigned for each segment simultaneously. However, there is a major 2026 exception for International Connections: if you are flying from an international destination into the U.S. and then connecting to a domestic Southwest flight, you must claim your checked luggage after clearing Customs and physically re-check it with a Southwest agent. Furthermore, if your connection involves a long layover (over 24 hours), it may be treated as a "stopover," requiring a separate check-in. For most 2026 travelers on a typical domestic layover, your bags will be tagged to your final destination, and you can proceed directly to your next gate using the same digital boarding pass.