Some devices get confused if there is only one DNS server provided by the DHCP… Maybe try setting your PiHole IP for both “Primary” and “Alternative” DNS server

The DHCP server pushes the DNS configuration to the clients. Is your Asus router running the DHCP server? If so, in DHCP configuration, set the DNS to point to your Pi-Hole

The only thing that comes to mind which would be our fault is a suboptimal internet connection when it comes to the Outlook not starting properly each time… but still not an excuse for it to get stuck in a background so we need a hacky solution like that shortcut I’ve made…

Thanks for the info, I’ve started using Quad9 ever since I got fiber recently and tried a DNS benchmark tool and saw it’s even faster than Cloudflare at my network

OpenDNS, anyone?