You can get a pass at the Southwest Ticket counter.
I've never had a problem with carry-ons with Southwest. In fact, I've brought a small travel suitcase (the kind with the retractable handle and wheels), a laptop bag and a purse and have never had a problem. The key is mostly in what fits in the overhead compartments - my suitecase goes in the overhead, the laptop bag under the seat in front of me and my purse in my lap.
You can get a pass at the Southwest Ticket counter.
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