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Tyler Olson
Tyler Olsonenterprise engineer

I build enterprise systems end to end.

Azure, Intune, Exchange, identity and PKI. I design and build the Microsoft estate a financial institution runs on, from on-prem to cloud, and I still love learning it. This site is where I keep the things I find cool, and a test of how far a static web app can go.

GitHub LinkedIn
01

Built end to end

Things I owned from design to done, not pieces of someone else’s build.

  1. pki

    Designed and deployed the PKI.

    ADCS from the ground up: autoenrollment, cloud Kerberos, and certificate-based network auth with 802.1X and EAP-TLS.

  2. identity

    Took ADFS all the way to decommissioned.

    Federation moved onto Entra ID, with Conditional Access across the tenant.

  3. passkeys

    FIDO2 provisioning at scale.

    Hardware keys enrolled through a PowerShell tool I wrote for the help desk: search the user, plug in the key, done.

  4. endpoint

    Autopilot both ways. Apple from scratch.

    Hybrid- and Entra-joined Windows builds on Intune, and the Apple side built new on DEP and Intune, migrated off Jamf.

  5. automation

    An overnight merger cutover.

    Security stack swapped, domains joined, the full app suite installed, all scripted in PowerShell. Users barely noticed.

  6. m365

    The layer nobody notices.

    Exchange and the M365 estate, plus the DNS, DHCP and print layer underneath. When it works, nobody notices. That’s the job.

identity
Entra ID · ADCS / PKI · FIDO2 · Conditional Access
endpoint
Intune · Autopilot · ConfigMgr · macOS / ABM
m365
Exchange · SharePoint & Teams · Power Platform
automation
PowerShell · Graph API · Logic Apps & Functions · Bicep
02

The lab

Experiments with local models on my own hardware, dated from their own logs. A negative result gets written up the same as a win.

    full notes on every experiment
    03

    Things I made

    Tools I shipped, and the parts of this site that exist because they’re fun.

    powershell · fido2

    Passkeasy

    Provisioning a hardware key through the portal is fourteen clicks too many. This wraps YubiEnroll in a menu the help desk can drive without a manual. The site’s namesake.

     browser-only · single file

    Teseasy

    A Tesla dashcam viewer. Point it at a folder of clips and review them as one continuous drive. The video never leaves your computer.

     8 cabinets · in the browser

    The arcade

    Turtles in Time, N.A.R.C., Total Carnage and friends through the Internet Archive, plus DOOM on this site’s own copy of DOSBox, compiled to WebAssembly.

     windows · an xp theme

    PasskeasyOS

    This whole site again, as a desktop you can drag around. A window manager in plain JavaScript. Best on a big screen.
    04

    This page, traced

    Measured in your browser just now. No framework and no build step: plain files on Azure Static Web Apps, and one Azure Function that talks to GitHub for everything live above.

    1. 01 · you Your browser    
    2. 02 · edge Azure Static Web Apps    
    3. 03 · serverless Azure Function    
    4. 04 · upstream GitHub API