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Very true, my co-founder discovered this the hard way.

A note on the roundtrip booking - correct, you should never book roundtrip. Your roundtrip should be made up from two one-way bookings.

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lol I am the aforementioned co-founder. This is definitely a flight booking hack with costs and benefits that have to be weighed. I don't personally book this way for savings of just 10-20 bucks. When it's something like $80 in savings or more (I saved >30% on my last flight), you start to think maybe the expected value will come out positive, even with all risks considered.

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