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As it is the public you are catering to, I feel you cannot reasonably ask them to install your SSL root certificate (how do they know you won't then mitm them on their home connections?). The process for this is also very technical and varies by browser. I feel your options are to maintain an IP blacklist, or to disable https connections entirely. For the ...


Consider the question you're asking ("How can I serve a blockpage instead of https://playboy.com without my users having to do anything") as "How can I serve my own version of https://trusted-bank.com without my users' knowledge". HTTPS and browsers are (these days) designed to avoid exactly this. This makes web filtering hard. Even if you pushed a wpad, ...

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