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First let me say I love Southwest and I have been a loyal customer for years. In years past I purchased my tickets weeks early and set an alarm to check in 24 hours prior to my departure to make sure I could get a decent low boarding pass, a very high A or a very low B number. I noticed a change when the Early Bird program came out. My method of checking in 24 hours prior to my departure now gave me a high B and sometime even a C number. This didn't bother me too much when I traveled alone but I recently got engaged and my fiance gets very nervous if I am not sitting with her due to her flight anxiety. I really have no choice but to purchase the Early Bird for each of us going both directions which sadly ends up being a lot of extra money especially if I need to change my reservations since their is no refund and Early Bird is not transferable. Hopefully Southwest will lower the price greatly or do away with this added cost.
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Non-refund on Early Bird definitely affects my decision to use it...especially at booking (typically 3-6 weeks in advance).
I have also seen that "buying" EB just before flight time often does not result in "very high A or very low B" boarding passes.
Flying in/out of Orlando getting an "A" is big...many, many families boarding at the start of B.
Wonder if your priority/pick is affected by the EB purchase date? Or is the occasional mid B number just a result of popularity of EB?
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Are you and your fiancé booking together? I would assume that is the tickets are booked together that when you check in you would be seated together. I have yet to fly with someone yet based on my flight history I would think this would be the case. As far as "Early Bird" I think there are a lot of people taking advantage of this program and at the same time this get mixed in with the "A-List" people so that's why you see such a change.
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EarlyBird Check-In positions are assigned based on the date of EBCI purchase. The earlier, the better.
EBCI positions will always come after Business Select (A1-15), then A-Listers (A16+).
Southwest places no limit on the number of EBCIs it will sell per flight, meaning that people get B and sometimes even C positions even after paying the extra fee.
EBCI isn't refundable, unless Southwest cancels the flight. But it is transferrable. As long as you use the "change flight" function, not cancel and rebook. As long as the confirmation number stays the same, the EBCI should transfer to the new reservation.
The date of that transfer becomes the effective "purchase date" for determining your EBCI position on the new flight.
Many, many, many people buy EBCI. In 2015, Southwest earned over $240 million on EBCI fees alone.