tyler olson · system engineer

The full Microsoft stack. On-prem to cloud, and the hybrid in between.

Identity, PKI, endpoints, M365, automation — the systems an institution actually runs on. Most of what I build was never assigned.

type help in the terminal → press / anywhere
G U E S T @ P A S S K E A S Y . C O M
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01 /about

The kind of curious that turns every answer into another question.

That curiosity has run a decade and change — help desk to system engineer, campus labs to a financial institution's entire Microsoft estate. Building for the people who use it, not for my own convenience.

Tyler Olson
Tyler Olson System Engineer · Wings Credit Union. Individual contributor — Microsoft enterprise stack, on-prem to cloud. linkedin ↗
always

How and why, not just what

Every system has logic underneath it. Finding that — regardless of what the system is — is the part that never gets old. Still asking the same questions, just with harder problems.

currently

The whole stack, not a slice

Deep in identity and PKI — ADCS, autoenrollment, cloud Kerberos, native passkey provisioning. But also Autopilot and Intune across Windows and macOS, Exchange and the M365 estate, and the unglamorous DNS-DHCP-print-server layer institutions actually run on. Invisible when it's right, very loud when it isn't.

track record

Most of it was never assigned

An overnight merger cutover scripted in PowerShell — security stack swapped, domains joined, full app suite installed, users barely noticed. An ADFS decommission. A passkey CLI. Saw what needed doing and did it.

how i work

Automate everything possible

PowerShell, Graph API, Proactive Remediations, Power Platform, Logic Apps, Bicep. If it can be scripted, it is. If it can't, it will be.

what's next

AI as a working partner

Staying on whatever's next — right now that's AI, used as a collaborator rather than a curiosity. This site was built with Claude: code, architecture, decisions. The gap between people who get this and people who don't is only going to grow.

02 /projects

More has been built than what's shown. This site exists because something needed to. What it becomes next is still forming.

Built after scrubbing through Tesla dashcam clips by hand one too many times. Point it at a folder of clips and review them like one continuous drive — nothing installs, nothing uploads, nothing leaves your machine.

browser-onlyno uploadssingle file
visit teseasy.passkeasy.com ↗

The portal flow for provisioning a hardware key is fourteen clicks too many. This wraps Yubico Developer Tools in a help-desk-friendly CLI so a new hire's key is enrolled in seconds, not minutes. The site's namesake.

FIDO2CLIhelp desk
github.com/Intranet-Explorer ↗
03 /tools

Built by people in the Microsoft community who actually use them. Worth bookmarking.

04 /arcade

Classic arcade games running entirely in the browser via Internet Archive iframes — no backend, no uploads, just Azure Static Web Apps doing what serverless does best. Scroll if you want, no pressure.

🕹️

Select a game below

— arcade —
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· · select a game below ↗ archive.org