Andrew Doering

The Model Context Protocol roadmap was updated today, and one line in it points at how agents will authenticate to enterprise systems for the next few years.

Over the past three weeks I got to go scuba diving for the first time, then snuba diving the day after.

Nine days ago I published a post explaining why Tailscale couldn’t route on the reMarkable Paper Pro.

I wanted Tailscale running on my reMarkable Paper Pro so I could reach SSH and a couple of internal services while traveling, without carrying a laptop just to jump through a bastion host.

Every morning at six, a container on my home server builds a fresh notebook and pushes it to my reMarkable, the same routine from rewriting the daily journal generator to stop generating PDFs and ship native, device-templated notebooks instead.

I’ve administered Okta for ten years now, and it’s been an enormously wild ride.

Azure Virtual Desktop can sign users in to their session host with a Microsoft Entra ID token instead of a Windows password.

Back in early 2024 I wrote about getting Device Trust working on our Azure Virtual Desktop estate.

If you have ever managed a fleet of Macs, you have seen this prompt: An update is ready to install.

A few months ago I wrote about Okta’s Device-Bound SSO, which welds an Okta session to a hardware key in the Secure Enclave or TPM so a stolen cookie is useless on any other machine.

Tip TL;DR: if you just want the tool, it’s open source - remarkable-ocr-handwriting: a small containerized daemon that watches a folder, transcribes new reMarkable exports with a local vision LLM (via Ollama), and writes searchable Markdown into your Obsi…

Every morning at six, before I’m awake, a small container on my home server builds a fresh notebook and pushes it to my reMarkable.

There’s a bass player I follow on YouTube, an Italian guy who goes by Davie504.

Det finns en basist jag följer på YouTube, en italienare som kallar sig Davie504.

I went to read an article about human.json and got served H.P.

This is Part 6 of a 6-part series on AuthZEN and the Shared Signals Framework.

This is Part 5 of a 6-part series on AuthZEN and the Shared Signals Framework.

This is Part 4 of a 6-part series on AuthZEN and the Shared Signals Framework.

This is Part 3 of a 6-part series on AuthZEN and the Shared Signals Framework.

This is Part 2 of a 6-part series on AuthZEN and the Shared Signals Framework.

This is Part 1 of a 6-part series on AuthZEN and the Shared Signals Framework.

The Problem: Your Session Cookie Is a House Key Under the Doormat If you manage an Okta tenant today, here’s the uncomfortable truth about what happens after your users jump through all those authentication hoops.

I recently completed a migration of our Microsoft 365 SSO federation from Google Workspace to Okta for our organization (~350 users).

There’s a category of security tooling that promises to protect your organization from insider threats by analyzing employee behavior.

This is Part 4 of a 4-part series on identity as the new security perimeter.

This is Part 3 of a 4-part series on identity as the new security perimeter.

This is Part 2 of a 4-part series on identity as the new security perimeter.

This is Part 1 of a 4-part series on identity as the new security perimeter.

The printer is dying.

Note Update (June 2026): This post solves the input problem - reshaping tall reMarkable exports so Vision LLMs can read them.

Introduction I received a reMarkable tablet for note-taking and document annotation over the holidays.

I have family members retiring soon, and apart from getting their laptops set up so that they have a low-maintenance life, there is an elephant in the room we don’t talk about.

After a routine reboot, my entire self-hosted infrastructure went dark.

When you can’t install Tailscale on a device - like a work laptop with MDM restrictions - but still need secure access to your homelab services, what are your options?

Solving the Okta Group Rename Headache: A Script to Export Push Mappings Hey there, fellow identity admins!

Home Assistant Automation Watchdog: Because Someone Always Clicks the Wrong Thing Introduction After running Home Assistant for several years now, I’ve learned that building reliable home automation isn’t just about writing good automations - it’s about m…

Introduction I have been using Sonos’ Alarms feature for some time to setup alarms for certain things, like waking up, but one thing always bothered me.

Introduction As we attempt to build out a more developer and technical driven operational workflows, this means that we need to have potentially non-technical support members, to be able to help and assist with those flows.

Note

Introduction At $currentJob, we wanted to allow our end-users of Okta, who are administrators in their respective platforms, to view or manage applications they are responsible for.

Introduction As part 6 has yet to be released pending approval from my work, here is a brief overview of part 5.

Introduction Last week we took on: Overview: Addressing Okta’s 100 network zone limit through automation with Terraform.

Why we need Privileges or why Apple needs to get better at admin-less actions Back in 2019-2020, I blogged about using Privileges as it was somewhat freshly out in the Apple Community.

Introduction Last week we discussed the following: Introduction: Exploring Terraform’s integration for Okta to manage infrastructure and groups.

Introduction Last week we went over the following: Overview: Automating group memberships and business line structures using Terraform.

Introduction Last week we discussed what went into Terraform and Github Pipelines, and Okta workspaces.

Introduction Just a brief recap from last week’s blog post, we covered: Introduction to Terraform: I began using Terraform for AWS in 2017 and expanded to IT services like Okta after its Terraform provider was released in 2019.

Switching the commenting system I have been using Disqus for some time since switching my blog, as it was the most common system at the time and felt like the most frequently used.

Introduction I was introduced to Terraform in June of 2017, as my employer was using Terraform to manage their AWS resources and infrastructure for our product as we moved from an on-prem colo datacenter to an AWS Infra-hosted environment.

What are we trying to achieve?