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I would just like to know if it is possible to use the Squid proxy server on an Ubuntu as a remote proxy server that when connected would allow someone to connect to a domain name with a custom TLD?

Thanks in advance, Francis P.S Please let me know if there is a better way to do this :D

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Yes, but you'd need to either set explicit host mapping in /etc/hosts for every system in the custom TLD or configure it as a DNS server with relevant records pointing to the DNS servers for the custom TLDs you want in much the same way as a default configuration already has for the root servers.

The OpenNIC Project already does this for a bunch of custom TLDs, like .pirate and .geek.

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