Enabling DoH on Windows Server 2025: A Guide for the Self-Loathing Administrator

Oh joy. Another steaming pile of “innovation” that nobody asked for except the tinfoil-hat brigade and the vendor lock-in specialists at Microsoft. DNS over HTTPS – because apparently regular DNS wasn’t making my life complicated enough. Now I get to troubleshoot encrypted DNS queries while Karen from HR screams that her “computer is broken” because she can’t access Facebook marketplace at her desk.

For those unfamiliar with this fresh hell, DoH wraps your DNS requests in HTTPS encryption. This means instead of being able to quickly glance at a packet capture to see why someone’s machine is resolving “malware-r-us.biz” every three seconds, you now get to play cryptographic whack-a-mole. The security team wanks themselves silly over it, though, so here we are.

Prerequisites (Or: Shit You Need Before the Misery)

Before embarking on this digital suicide mission, ensure you have:
• Windows Server 2025 Preview Build 26063 or later (because production servers love running beta code)
• Windows 11 22H2+ for clients (time for forced upgrades, bitches)
• A DoH-capable resolver like Cloudflare, Google, or Quad9
• Administrative rights and a developing substance abuse problem

Server Configuration: The Easy Part (Surprisingly)

First, enable this monstrosity on your DNS server. Fire up PowerShell and sacrifice dignity to the syntax gods:

Set-DnsServerSetting -EnableDoH $true

Shockingly, that’s not the worst part. Now you must feed it actual DoH servers, because enabling DoH without servers is like buying a car with no engine – technically a car, but fucking useless.

Add-DnsServerDohServerAddress -ServerAddress 1.1.1.1 -DohTemplate https://cloudflare-dns.com/dns-query -AutoEnable $true

Add as many as your paranoid heart desires. Verify it with:

Get-DnsServerDohServerAddress

If you see output, congratulations. If not, check your firewall isn’t blocking port 443, or that you didn’t typo the URL like a muppet.

Client Setup: Where Dreams Go to Die

Now to inflict this upon your users. Two methods, both equally shit:

Group Policy Method:
Navigate to Computer Configuration > Administrative Templates > Network > DNS Client. Find “Configure DNS over HTTPS” and set it to Enabled. Choose “Automatic” discovery (ha!) or “Manual” where you hand-craft template URLs like a peasant. Deploy to an OU and watch the chaos unfold.

MDM Method:
If you’re fancy and have Intune, create a device configuration profile. The CSP is ./Device/Vendor/MSFT/Policy/Config/DNS/ConfigureDoH. Push it out and pray to the MDM deities it doesn’t brick half your fleet. If you’re using anything else, well, enjoy your manual configuration, champ.

Verification: Proving the Pain Is Real

Run this on a client to see what DoH servers it’s supposedly using:

Get-DnsClientDohServerAddress

Then actually test the bloody thing:

resolve-dnsname github.com -https

Look for “QueryType : HTTPS” in the output. If you see it, the encryption is working and your monitoring tools are now worthless. If you don’t see it, something’s broken and you’ll spend the next six hours troubleshooting TLS handshakes instead of real problems.

Conclusion: Was It Worth It?

In summary: you’ve encrypted DNS queries, broken your ability to see what’s happening on your own network, satisfied some auditor’s checkbox, and given yourself a migraine. The queries are now hidden from ISPs and nosy neighbors, which is great if your threat model includes “someone cares that I’m checking ESPN.com during work hours.”

It hasn’t stopped Dave from clicking that phishing link, though. But sure, let’s call it a security win.

Article link for the masochists who want the full gory details: https://4sysops.com/archives/enable-doh-dns-over-https-in-windows-server-2025-dns-server-configure-windows-11-dns-clients/

Anecdote: Had a management consultant ask me last month if our DNS was “zero trust compliant.” I told him we implemented DoH specifically to trust zero people, especially not the users. He billed the company $500 for that insight. I billed my liver for the six whiskeys it took to not strangle him.

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