For anyone reading this message and wondering what the solution is:
It seems you have requested a certificate but not installed it. The installation checker only verifies if your website returns a correct SSL certificate. Since you’re using Cloudflare, it returns Cloudflare’s certificate.
The error you got without the VPN indicates that there is no SSL certificate installed on your site. The error with a VPN also indicates that there is no valid SSL certificate installed. The error is different with and without VPN because of DNS cache.
The redirect loop is caused by Flexible SSL, which WordPress can’t deal with properly on it’s own. But with a bit of configuration, you can make that work:
Alternatively, you can forego Flexible SSL and either:
- Request a “Self Signed” certificate and use Cloudlfare in “Full” mode.
- Request a certificate from Let’s Encrypt or another trusted provider and configure your site with “Full (strict)” mode. This is the most secure option, but you need to manually renew the SSL certificate on your hosting account every 2-3 months.