Microsoft Cloud PKI: Because Fucking Up Certificate Management Wasn’t Easy Enough Already
Oh brilliant, just what I needed—another half-baked Microsoft service in public preview that makes me want to chainsaw my own network backbone. Microsoft Cloud PKI, they call it. Sounds fancy, right? Like it’ll magically solve all your certificate headaches. Spoiler alert: it won’t. It just moves the migraine from your on-prem CA to the cloud, where you can pay for the privilege of being equally pissed off.
So here’s the deal, and try to keep up because I’m not drawing you a fucking diagram. You get two CAs: a Root CA that can live up to 50 years (because apparently, Microsoft thinks you’ll be dead before that becomes a problem) and an Issuing CA that maxes out at 10 years. The certificates you push to devices? They’re capped at 5 years for Intune enrollment and 2 years for S/MIME. Why? Because fuck consistency, that’s why.
The Issuing CA allegedly “automatically renews” 60 days before it expires. Big. Fucking. Deal. It’s the Root CA that’ll bite you in the arse. When that bad boy approaches expiry, there’s no nice “renew” button. No, you get to manually recreate the entire goddamn hierarchy from scratch like it’s 1998 and you’re setting up your first Windows NT domain.
The process is a seven-layer shit-cake: create a new Root CA, verify it (because blindly trusting Microsoft is how you end up explaining a breach to the board), create a NEW Issuing CA under that Root, mark the old Issuing CA as inactive, wait for all devices to get the new certs, then clean up the old CA like you’re erasing evidence of a crime. All while praying you don’t brick every mobile device in the company.
And the best part? Microsoft’s documentation is silent on what happens to existing certificates when the Root CA finally kicks the bucket. Do they fail? Do they keep working? It’s a mystery box of fuckery. You’ll need PowerShell scripts to monitor this mess because the Intune portal sure as shit won’t give you proper warnings. The Get-MgBetaDeviceManagementCertificateConnectorDetail cmdlet becomes your new best friend, not that you wanted one.
Bottom line: this isn’t managed PKI. It’s PKI that you’re paying Microsoft to let YOU manage, just with prettier dashboards and more opaque failure modes. Start planning your Root CA rotation now, because 50 years sounds like forever until you’re 49 years and 300 days into it, and suddenly the CEO’s iPad stops trusting the VPN.
Anecdote: Last week some middle-manager who calls himself “cloud-forward” asked why we can’t just “extend the certificate like we do with Teams meetings.” I explained PKI trust chains using the analogy of house keys and lock smiths. He nodded, then asked, “So can we just call the lock smith?” I told him yes, absolutely, and gave him Microsoft’s support number. He’s still on hold. I consider it a win.
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