I have seen this same scenario posted elsewhere and Southwest absolutely will not extend the credit (for a fee) until after it actually expires. Sorry to inform you but they will not budge on this. In my opinion, and in agreement with previous posts, I really don't think you'll have a problem waiting until the 8th or 9th to book your trip for the 30th as you still have a three week advance and most of Southwest's cheapest fares only require a two week advance purchase.
If, however, this trip is for an important event (wedding, Bar Mitzvah, family reunion, etc.) and you really want to lock in the tickets then I'd say go ahead and book them now. You can then call Southwest on the 8th or 9th and pay the fee to have the unused funds extended and apply that to a future trip.
One thing I will recommend in either scenario and that would be if you currently have two credits totaling over $700 you should combine them into one credit by booking a "dummy" trip before the funds expire. If the credits remain separate you'll pay two $50 fees to extend them however if they are first combined into one ticket you'll only pay one $50 fee to extend and then can use them for another two tickets later.
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