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Re:Chrome 68 will mark all HTTP sites as “not secure” by AdamJacobMuller on Saturday February 10, 2018 @02:11AM (#16346290)
Register domain called X.com

Set up a DNS server that, for a domain of 10-0-0-1.$rand.X.com returns 10.0.0.1

Generate DNS challenges for your domain, issue lets encrypt certificates for said domain.

Viola, private, local, publicly-trusted, SSL-encrypted.

Have http://10.0.0.1/ redirect to https://10-0-0-1.$rand.x.com/

The biggest issue with this is getting LetsEncrypt to issue you enough certificates.

PS: this idea is somewhat borrowed from Plex.

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