Funds applied to a new itinerary cause that new itinerary to take on the earliest expiration date of any funds. Now, more than every, you must read the fine print -- for all transactions that involve a significant amount of money. Southwest doesn't ever extend expiration dates, but they may be able to reissue the funds as a voucher, minus a $100/passenger fee. You'll need to talk to Customer Relations at 1-855-234-4654 (not the main number). These requests are granted on a case-by-case basis. You have 6 months after expiration in which to make the request, and once issued the voucher is valid for 6 months, and is usable by anyone. Good luck.
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