Southwest Airlines just nickel-and-dimed some customers at the worst possible time

The little things matter to your regular customers. They can matter even more if you pick an imperfect time to do them.
Written by Chris Matyszczyk, Contributing Writer
Plane in blue sky with clouds
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Let's think about all the good things Southwest Airlines does.

It doesn't charge you bag fees. It doesn't charge you for changes or cancellations. Its rewards points don't expire.

All this is currently quite easy to forget, given the airline's long and winding debacle at the end of 2022.

Why, renowned travel industry analyst Henry Harteveldt recently mused that some customers are still steering clear of Southwest. This, he said, had engendered in the airline "a moderate state of panic."

What do you do when you're in a moderate state of panic? Me, I watch sports and pretend it's me playing on the TV. A glass of decent pinot noir helps.

Also: The best sports streaming services

But Southwest has tried to pull off the idea that it's business as usual. Why, the airline even wants its customers to propagate that idea and recommend Southwest to businesses so that airline can get more corporate business.

But if there's one thing business travelers don't like -- oh, all travelers really -- it's when they feel they're being nickel-and-dimed.

I can imagine, then, that one or two Southwest customers will be peeved at the airline's latest announcement. As Travel and Leisure reported, Southwest is changing how it's charging for Wi-Fi.

It used to be that you could get a single-day Wi-Fi pass for a mere $8, valid for all Southwest flights that day. This was especially kind to those customers who were connecting from one Southwest flight to another.

What a way to build loyalty by saying: "Nah, you've paid us once already for Wi-Fi. Why should we charge you again on the same day? That's not love."

Ah, but these are challenging times, so the fee will now be $8 per flight.

Also: In-flight Wi-Fi is a nightmare, but fixes could be on the way

The airline has an explanation, one that's entirely believable: It's trying to make its Wi-Fi better, which costs money.

Southwest's Wi-Fi hasn't always enjoyed the best of reputations. Some regular flyers can even get into spats over whether it's slightly worse or slightly better than United's.

So now Southwest is introducing Viasat Wi-Fi to some of its planes, something that airlines like Delta are now offering for free.

It's clear Southwest is conscious that not everyone will enjoy having to pay a total of $16 for Wi-Fi, should they be having to leap onto a connecting flight.

In a statement, the airline pleaded: "This impacts a small subset of customers due to our robust network of nonstop flights, free onboard entertainment, and a limited number of customers choosing to use paid internet across connecting flights."

Also: Here's how to keep your home secure when you travel

Of course it's a limited number. Most numbers are. But I still wonder how big the number is. If it really is a teeny-tiny number, then why do this at all?

Sadly, anything adorned with even the mildest whiff of unhelpful news won't go down well with the flying masses.

I feel sure, though, that Southwest's accountants and other fine executives are now furiously tossing out ideas on how to win back those whom the airline so heinously let down.

Ideas that won't cost the airline too much, that is.

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