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Is it possible to enter Thailand on a visa-free program with one passport (expires in February), and leave on a new passport for 5 years? It turns out without entry stamps.
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They may not let you in if the remaining validity period of the passport is less than 6 months.
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I entered Kyrgyzstan with one passport, and left with another (similar to your situation with the old/new ones), but there are no such visa problems there.