December 1, 2023

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Southwest Hawaii Vacation Risk | Pilot Strike Warning + $1B Problems

Southwest Airlines Pilots Strike Vote

We are getting emails and messages asking the same question. Should we book a Southwest Airlines Hawaii now, given several uncertainties? Our answer is below, but first, the issues that could influence your decision. Also, we’ve thoroughly enjoyed our fall flights with Southwest, as you can read about in this Southwest Hawaii review. But would we jump on a Hawaii flight with them right now?

While a plan is coming into place, Southwest systems aren’t yet capable of managing massive interferences such as the big storm that hit over the holidays. That resulted in 15k flights canceled, plus untold problems with delays, mishandled baggage, and more. Unlike the aviation industry has ever seen.

Pilots’ union seek strike authority.

SWAPA, the SW Pilots union, will hold a first-ever vote to provide it the authority to call a potential strike. While such an eventuality may not be likely, it indicates the severe tension and bad feelings pilots have after being stranded by Southwest over the holiday disaster, among other things. Pilots have also been unable to reach an agreement with the airline after years of negotiations.

Union president Casey Murray said regarding seeking a strike vote authorization, “This decision is not one based on emotion, but I would be lying if I said that I wasn’t angry.” He also seeks “gratitude pay to compensate our Pilots who suffered through the meltdown.” The voting begins May 1.

We want to “Give our customers time to book elsewhere so that they may have confidence in their summer vacations, honeymoons, and family outings.” — SW Pilots’ Union president.

You may recall that Delta also faced a similar situation in some ways with their pilots when they authorized a strike vote last fall. A preliminary deal was subsequently reached.

Nearly $2 billion in unexpected costs complicate things.

It is estimated that the December meltdown will end up costing Southwest some $800 million. Not only that, but Southwest CEO Bob Jordan said that the company will invest an additional $1 billion to improve its infrastructure and prevent a reoccurrence of their problems. He said the company is “Currently budgeted to spend more than $1 billion of our annual operating plan on investments, upgrades, and maintenance of our IT systems.”

The highlights and action plans described by Bob Jordan in a recent email to his customers are:

  • Establish supplemental operational staffing that can quickly mobilize to support Crew recovery efforts.
  • Enhance crew engagement technology to efficiently communicate with large numbers of Crew Members during frequent schedule changes.
  • Updating and upgrading our Crew recovery system to not only solve current and future schedules but also provide the ability to optimize established schedules as we revise them during irregular operations
  • Hire a third-party global aviation consulting firm, Oliver Wyman, to complete an assessment of the event and make recommendations of additional mitigation elements for us to consider.

Should you fly to Hawaii on Southwest?

The answer depends on where you fit below:

1. Non-Loyalist: Given the current problems, non-loyalists might consider alternative airlines over the upcoming months. It will take time for Southwest to fix billion-dollar technology problems and deal with its pilots. Neither will be resolved quickly, leaving passengers vulnerable to those issues. The sad thing is this could have all been avoided had Southwest been more proactive and updated its ancient technologies earlier.

2. Loyalists: there’s no question, as they will almost always choose Southwest for many good reasons.

3. Placebound: Some cities are easier to travel from/to using Southwest because the airline is so well positioned. And that will be part of your decision.


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