macOS Platform SSO with Entra ID via Apple Business (No Intune Required)

The Problem A small business running Microsoft 365 with no existing Intune footprint wanted phishing-resistant, hardware-bound MFA their Macs: the same Windows Hello for Business-equivalent experience, but for macOS. Apple’s answer is Platform SSO (PSSO) with a Secure Enclave-backed key, and Microsoft’s Entra ID plugin supports it. The problem: virtually every piece of public documentation for this assumes Intune. This organization didn’t have an Intune license and didn’t want to buy one just to push a single configuration profile. ...

August 21, 2026 · 11 min · Zac Lohrenz

Migrating a 107GB Gmail Mailbox with LAO: What Microsoft's Docs Don't Tell You

Migrating a single Accounts Payable mailbox from Google Workspace to Exchange Online should have been the easy part of a larger phased migration. It wasn’t. The mailbox was 100GB+ with 600,000+ items, which put it past Exchange Online’s standard migration path and into Large Archive Onboarding (LAO) territory. LAO is the only supported mechanism for migrating a mailbox this size from Gmail while splitting content between primary and archive by date or folder. ...

August 12, 2026 · 9 min · Zac Lohrenz

1Password Storing Your OTP Is Not MFA

The Claim Under Test If your password and your TOTP seed live in the same 1Password vault, unlocked by the same master password, you are running two-step verification (2SV), not multi-factor authentication (MFA). Same secret store, same unlock event, same attacker who now has both factors the moment they get one. This isn’t a hot take. It’s already worked out, published, and ignored, largely because PCI DSS Requirement 8.3 only mandates two factors from two categories, not factor independence or phishing resistance, and most cyber insurance underwriting still treats SMS OTP as an acceptable floor for standard users, even as carriers increasingly downgrade or reject it for privileged accounts. It’s really the same reason why faxing in the USA is considered acceptable for patient health data: HIPAA’s Security Rule requires reasonable and appropriate administrative, technical, and physical safeguards for transmitting e-PHI, not a specific transmission technology, so fax was never excluded and never got re-evaluated once better options existed. Not because either is safe or secure: because it’s legacy knowledge enshrined in permanance. The compliance bar and the security bar diverged years ago for MFA and 2SV; the industry kept building to the compliance bar. ...

July 24, 2026 · 11 min · Me

Debugging DNS Resolution in Tailscale Exit Nodes: A dnsmasq Configuration Guide

The Problem: Selective Network Outages Over Tailscale When users reported that database access through a Tailscale exit node was failing while RDP connections remained functional, the initial symptoms suggested a routing or firewall issue. However, the real culprit was much more subtle: DNS resolution was being silently dropped at the exit node level. Why This Setup Exists at All: Azure Private Link Resolves Differently Depending on Where You’re Standing Before getting into the dnsmasq “bug” itself, it’s worth explaining why this infrastructure exists in the first place, because the root problem isn’t Tailscale or dnsmasq, it’s that Azure Private Link’s DNS behavior is context-dependent, and a VPN mesh network doesn’t naturally live in any single context. ...

July 17, 2026 · 12 min · Me

The 'Wait a Patch Cycle' Doctrine Is Dead, and Most SREs Haven't Noticed

SREs split into two camps, and neither one is fully right. The first camp matured out of operational IT. They’ve lived through a bad patch Tuesday, a driver update that bricked a fleet, a vendor hotfix that took down a cluster. Their instinct: let a patch cycle pass before you touch it. Let someone else find the landmine. This dates me, but is the world I learned in myself. The second camp never did operational IT work. They came up through cloud-native, IaC, CI/CD. They don’t have the scar tissue, but they inherit the doctrine anyway, because the first camp is louder and… has tenure. ...

July 2, 2026 · 5 min · Zac Lohrenz