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I'm not sure if you're speaking from personal experience, but most I've interacted with don't have to worry about the self-signed vs. LetsEncrypt debate. They just don't do it. Also there would be no way to do LetsEncrypt as the system is air gapped.

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You can do DNS challenges for air gapped networks as long as the TXT records resolve publicly.

So then you have a signed CSR right? How would you get the certificate onto the box?

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