I am SO glad you made this post. YES! I have had the same issue for the past 2 years. I purchased an upgrade about 2 years ago, and EVERY TIME SINCE I HAVE BEEN GIVEN A BOARDING GROUP position that is at least at the end of the A group and usually in the B Group. Also, to respond to the nay-sayers, I always, without fail, check in the moment the clock ticks 24 hours from the flight time. It happened a few times and I thought it was my imagination. I have now started keeping a log (I fly a lot for business) and it has happened EVERY flight, without fail. I remember the old days when I used to get an A20 or A30, but that literally has not happened since I purchased an upgrade. I am keeping the log because I would be willing to bet that there are others out there who have had the same issue. By the way, to those Southwest reps posting on here, in the past 2 years I actually moved to a new city and it still is happening. I have flown to many different locations (both direct and with legs) all over the country and it has happened without fail. If I bet against the odds of this happening, I would have been able to buy my own jet by now! I am actually surprised that Southwest would be so blatant about this as a simple IT audit could easily uncover the truth here.
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