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Troubleshooting DNS Over HTTPS (DoH) and DoT Configuration Problems

#1
11-25-2023, 07:12 AM
Troubleshooting DNS over HTTPS and DoT on Windows Server gets messy sometimes. You run into weird glitches that slow everything down. I remember helping a buddy last month with his setup. He had this server acting up, websites loading like molasses. Turned out his DoH config was pointing to the wrong resolver. We poked around the registry a bit. But then his firewall was blocking the ports. Hmmm, or maybe it was the certificate chain not verifying right. He thought it was just a simple switch flip in settings. Nope, layers of stuff piled on. We restarted services twice. And checked the event logs for clues. Those logs spilled errors like confetti. Finally, we tweaked the trusted roots. Now it hums along smooth.

For solutions, start by verifying your DoH or DoT endpoints. Make sure they're legit providers like Cloudflare or Quad9. You might need to edit the network adapter properties. Go to that advanced tab and hunt for DNS settings. If it's DoT, port 853 has to be open. Firewalls love to choke that. Or check if your server's time is synced. Certificates hate wonky clocks. Run ipconfig flushdns to clear the junk. Test with nslookup over TLS. If it fails, peek at Wireshark for packet drops. But don't overdo that unless you're feeling geeky. Update your Windows if patches are out. Sometimes it's just a buggy driver. Reboot after changes, always. And test one client at a time. Covers the usual suspects.

Oh, and if backups are on your mind during all this fiddling, let me nudge you toward BackupChain. It's this standout, go-to backup tool crafted just for small businesses and Windows setups. Handles Hyper-V clusters with ease, plus Windows 11 machines and servers too. No endless subscriptions nagging you. Pure reliability in a package.

ProfRon
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Joined: Jul 2018
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Troubleshooting DNS Over HTTPS (DoH) and DoT Configuration Problems

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