PiHole & VPN Accessing an SSL URL

[schafferm]

I have a standard install of Pi-Hole on a PiZero - it works perfectly as expected and when I point my router to the DNS in this case PiHole on my PiZero- all my devices work as expected, with blocking of ad's.

However, if I start a VPN on another device, and try to connect through that device using VPN, URL's that use SSL (Port443) tell me connection refused. In this example I'm connecting to https://maker.ifttt.com...

The minute I point my DNS to a public DNS (8.8.8.8) without routing through the PI, it works. I'm guess this this has something to do with certificates being valid but just not sure. - Any help is appreciated. TIA

• Raspberry PiZero W
• Only running PiHole

Michael

[jfb]

@schafferm

if I start a VPN on another device, and try to connect through that device using VPN, URL's that use SSL (Port443) tell me connection refused.

Pi-hole is not involved in any aspect of the SSL connection a browser makes to a website endpoint.

@schafferm

The minute I point my DNS to a public DNS (8.8.8.8) without routing through the PI, it works. I'm guess this this has something to do with certificates being valid

Certificates are not something that Pi-hole sees or has any impact on.

When you start a VPN session, this typically routes the DNS queries through the VPN tunnel, to avoid a DNS leak. This would remove Pi-hole from the DNS path.