This is pretty unacceptable at this point that they still do not have consistently functioning wi-fi on their aircraft.
When you look at what competitors are doing, their wi-fi is fantastic compared to 15 years ago, and easily attainable for free. However, I feel like Southwest's in flight wi-fi offer doesn't really function any better today than it did 15 years ago, but it sure costs more for those who are paying for it (remember the old system that let you buy it once and use it until your final destination)?