The reason that it has taken this long for Southwest to have in-flight wi-fi at all is that Go-Go fought them when they wanted to price it at $4.95. The planes and the towers to which they connect to the Internet don't have the capacity that a low price-point would bring. They price the connectivity out of the range of some customers intentionally.
This wi-fi is NOT what you are used to getting on the ground unless you use your smart phone for your Internet connectivity. You only get cell-speed connect AT BEST and the more customers buying it on a flight, the slower your connection will be. If you try to stream content, the Go-Go system is programmed to boot you off and make you spend a lot of time trying to reconnect so that the other passengers can use the limited bandwidth you were hogging. This is also why connectivity will never be free. They HAVE to get you to agree to their t & c (terms and conditions) so that they can then quote their rules and not give you a refund.
You are far better off bringing some other form of entertainment onto the plane, unless you like sharing your bandwidth with every other passenger who purchases connectivity. Go-Go's policy is no refunds so if you have an issue, whether it is their fault or yours, all you get, if you can wangle it at all, is credit for connectivity on another flight.
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