Long read but hopefully helpful. The Cliff Notes version is to avoid Southwest like the plague if you're a frequent flier. Southwest is pretty pathetic when it comes to customer service for loyal customers. I've been A-List for over two years and have held a Companion pass for over two years and that's through credit card spending and flights for business and leisure, not accumulation through opening cards and other advertising deals. They do not deviate from policy. You can be a first time flier or someone who has 1,000,000 miles, they don't care. That's probably good news for an infrequent Southwest flier, but it's again, pretty pathetic, if you fly with them only. While I was part of this "Top Tier" for Southwest these were some of my poor experiences with them: (1) They sent off a plane from Las Vegas with 20+ open seats after they would not waive the flight transfer fee for my pregnant wife and 2 year old when we tried to get on an earlier flight. As an A-List member the transfer fee was waived for me (policy) but instead of sacrificing the $150 for a "Top Tier" loyal customer, they opted to send the plane off with 20+ open seats (no deviation from policy). (2) I had purchased a flight to Hawaii for myself and my wife ($800 roundtrip) right before I hit Companion. So when I hit Companion I added my wife for that flight and cancelled the purchased flight so she got $800 in funds to her name. Well, since you have to use the $800 in a year but she was my Companion for the next year, I was essentially out $800. I called Customer Service and they said they could transfer her funds to me but that they'd take a $100 transfer fee. No flex at all in waiving that fee, didn't matter that I took 60 flights with them that year. (3) Amidst all this COVID crap I will say they've been good about extending dates (big deal, so has every other airline). Now that things are looking up we decided to book some travel for the upcoming year and what better time to use the funds from #2, right? WRONG. Southwest doesn't extend "Vouchers", which is apparently what the funds were transferred to in #2. Again, doesn't matter that I'm A-List or a Companion Pass holder. Doesn't matter that there was a global pandemic when my voucher expired. Doesn't matter that it was $800 of my cash. Southwest not only stole $100 of my money to transfer the funds from my wife's name to mine in #2 (really big effort and expenditure on their end to re-type a name, right?), they then stole the remaining $700 without ever notifying me that all the other 'expiration date extension' emails did not apply to vouchers. Reminder, this is not a LUV Voucher in the sense that Southwest gifted me $800 for giving up my seat. That was $800 of my money that was used to purchase a flight that was cancelled. I called, I wrote, and I got an email that basically told me to get bent but thank you so much for your loyalty. Bunch of BS. Their customer service is atrocious. All in all, not only have my experiences absolutely sucked lately with them, I know plenty of people who fly other airlines and receive top-notch service for their loyalty. With the amount of miles I've accumulated with Southwest I'd be upgraded to first class every flight on any other airline and be sitting in a lounge before flights with comp'd food and beverage. Do not fly Southwest or look at RapidRewards as anything other than monetary rewards (e.g. points). Your loyalty means nothing to them and your 1,000,000 flights or points gets you the exact same treatment as the guy who opened the credit card for his first ever flight on Southwest for free. Again, that's great news for the casual flier or bargain flier but horrible for anyone who will fly frequently. Take your business elsewhere. When I use up my 300,000 points and vouchers, I'm cancelling my Southwest credit cards and will never fly with them again.
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