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Cake day: June 1st, 2023

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  • I’ve fixed the same issue for me.
    Originally I had this in my Local DNS settings in my Pi-Hole:

    - service1.domain	10.0.0.4
    - service2.domain	10.0.0.4
    - service3.domain	10.0.0.5
    

    I changed that to this:

    - host1.domain		10.0.0.4
    - host2.domain		10.0.0.4
    

    And then I added CNAME Records to the services like this:

    - service1.domain	host1.domain
    - service2.domain	host1.domain
    - service3.domain	host2.domain
    

    This fixed the whole thing for me :)

    Edit: Gonna add some more info

    The trick that makes this work, and probably will for you too, and allow you to keep your HTTPS queries, is that Pi Hole will just not ask upstream, if it has the DNS name in the CNAME records. Those CNAME records will have to point to a domain, that Cloudflare doesn’t know about. That way there is no other records upstream that will confuse the DNS server and your browser.
    The hostname you have in your local DNS records that your CNAME points to, will be something only known locally for you.