At my wits end, this simply doesnt work. SITE IS DOWN

Server
2

Hi @Squidblacklist

the tls-sni-01 - challenge is deprecated. Support ends 2019-02-13

So it's better you switch to another validation.

There is your DocumentRoot.

So try (one line)

certbot run -a webroot -i apache -w /var/www/www.squidblacklist.org/ 
-d squidblacklist.org -d www.squidblacklist.org

You have two ip addresses.

Your configuration

Domainname Http-Status redirect Sec. G
• http://squidblacklist.org/
104.24.110.41 301 http://www.squidblacklist.org/ 0.233 D
• http://squidblacklist.org/
104.24.111.41 301 http://www.squidblacklist.org/ 0.230 D
• http://www.squidblacklist.org/
104.24.110.41 200 0.230 H
• http://www.squidblacklist.org/
104.24.111.41 200 0.230 H
• https://squidblacklist.org/
104.24.110.41 301 http://www.squidblacklist.org/ 1.416 F
• https://squidblacklist.org/
104.24.111.41 301 http://www.squidblacklist.org/ 3.310 F
• https://www.squidblacklist.org/
104.24.110.41 200 1.477 B
• https://www.squidblacklist.org/
104.24.111.41 200 1.480 B
• http://squidblacklist.org/.well-known/acme-challenge/check-your-website-dot-server-daten-dot-de
104.24.110.41 301 http://www.squidblacklist.org/.well-known/acme-challenge/check-your-website-dot-server-daten-dot-de 0.234 D
• http://squidblacklist.org/.well-known/acme-challenge/check-your-website-dot-server-daten-dot-de
104.24.111.41 301 http://www.squidblacklist.org/.well-known/acme-challenge/check-your-website-dot-server-daten-dot-de 0.223 D
• http://www.squidblacklist.org/.well-known/acme-challenge/check-your-website-dot-server-daten-dot-de
104.24.110.41 404 0.243 A
Not Found
• http://www.squidblacklist.org/.well-known/acme-challenge/check-your-website-dot-server-daten-dot-de
104.24.111.41 404 0.230 A
Not Found

looks ok, your /.well-known/acme-challenge - subdirectory doesn't send nonsense.

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