PowerShell + DevOps Global Summit 2026

Managing software on Windows at scale can often feel like herding cats; however, when you combine the declarative power of Ansible with the package management reliability of Chocolatey, it becomes a piece of cake.

In this session, we will unwrap the chocolatey.chocolatey collection, exploring how it provides a complete recipe for declaratively managing packages across your Windows fleet. We will look at how to mix the right ingredients (idempotency, configuration, and source management) to bake a reliable automation strategy that always rises to the occasion.

Whether you are strictly open-source or using Chocolatey for Business, you will leave this session ready to write playbooks that are undeniably sweet.

Handmade chocolate is charming. Handmade Chocolatey builds? Not so much. When your packages rely on copy-paste scripts, tribal knowledge, and “run this step next,” things fall apart—especially at scale.

In this session, we’ll move from artisanal, hand-rolled Chocolatey builds to repeatable, factory-grade automation using psake. You’ll learn how psake can orchestrate building Chocolatey packages, extensions, and related tooling with clear structure, dependency management, and predictable outcomes. These patterns come from real-world use in large, fast-moving environments where Windows automation needs to be reliable, auditable, and boring in the best possible way.

Drawing on experience maintaining psake itself and applying it in organizations operating at massive scale, this talk focuses on practical techniques you can use immediately—whether you manage a handful of internal packages or thousands of endpoints.

Patch happens—often at the worst possible time. In this session, we’ll show how Chocolatey for Business helps organizations bring control and consistency to software management through automation, standardization, and self-service. Learn how to reduce manual effort, improve security, and turn patching from a chaotic scramble into a predictable, low-stress process.

In this session, we'll review Chocolatey's Central Management platform, exploring its features and use for both simple software installations and upgrades, and moving into more advanced use cases, including leveraging its robust API.

If you're looking for a streamlined way to manage software within your organization, this session will shed light on one of Chocolatey's sweetest products.

PowerShell isn’t just for sysadmins and DevOps pipelines; it’s also a powerful tool for making your everyday life easier, more efficient, and even a little more fun.In this lighthearted but practical session, I’ll share real-world ways I’ve used PowerShell outside the data center and beyond the cloud. From automating the hunt for our dream home, to organizing and deduplicating thousands of old family photos, to sending real-time weather alerts to my kid’s soccer team, and even assigning Secret Santas. PowerShell has been my go-to companion for solving real-life problems with code.We’ll walk through the scripts, logic, and thought processes behind these solutions. You’ll leave with a fresh perspective on what’s possible with PowerShell, along with tips for building your own everyday automations.Whether you’re looking for clever ways to sharpen your skills or just want to see what a little scripting creativity can do, this session will open your eyes to the power of PowerShell in your own life.

As organizations scale their Windows automation practices, accessibility is often treated as an afterthought addressed late, inconsistently, or only when issues arise. Yet accessibility is not just a UI concern; it intersects deeply with automation, configuration management, deployment workflows, and the overall reliability of enterprise environments. This session explores how accessibility principles can be embedded into automated Windows ecosystems using Chocolatey, PowerShell, and modern DevOps tooling.

Drawing from real‑world experience in digital accessibility and inclusive design, this talk demonstrates how accessibility thinking strengthens automation quality, reduces operational friction, and improves user experience for everyone, not only people with disabilities. Attendees will learn how to incorporate accessibility checks into CI/CD pipelines, package deployments, documentation workflows, and configuration baselines. We’ll also explore practical strategies for making internal tools, scripts, and automated processes more inclusive for administrators, engineers, and end users with diverse needs.

Whether you’re managing large‑scale Windows environments, building internal automation tools, or maintaining enterprise packages, this session provides actionable patterns to elevate both accessibility and operational maturity. Accessibility isn’t a separate track, it’s a force multiplier for automation done right

Chocolatey packaging is often learned by example—and sometimes by accident. When packaging code lives outside of source control, teams lose context, history, and confidence.

In this session, we’ll break down why Chocolatey packages should be treated as versioned code and how even simple Git usage dramatically improves reliability and maintainability. We’ll cover common beginner mistakes, a sensible repository structure, and how source control enables safer changes and easier automation. Whether you manage one package or many, this talk will help you build packaging workflows that won’t surprise future you.

Automation is critical to scaling IT environments, improving reliability, and reducing manual toil. In this 4-hour, hands-on workshop, you’ll go beyond theory and learn how to design, build, and deploy an end-to-end automation solution using Ansible—enhanced with PowerShell for cross-platform and Windows-specific tasks. Together, we’ll tackle a realistic infrastructure scenario, giving you practical skills to automate complex workflows across Linux and Windows systems.We’ll start with a concise overview of Ansible fundamentals—inventory files, YAML playbooks, roles, and modules—before diving into PowerShell integration for Windows automation. From there, you’ll follow along in a live lab to build automation that provisions servers, configures services, applies security hardening, and orchestrates application deployment across multiple nodes. By layering Ansible’s orchestration strengths with PowerShell’s depth on Windows hosts, you’ll see how to create a truly hybrid automation strategy.This is a fully interactive workshop: you’ll write your own Ansible playbooks, integrate PowerShell scripts, troubleshoot failures, and iterate on your work until it’s production-ready. By the end, you’ll have a complete, functioning project that demonstrates the value of combining open-source tools with native scripting to solve real-world challenges.Key topics covered include:Setting up Ansible for Linux and Windows automationWriting Ansible playbooks and roles to orchestrate multi-tier environmentsUsing PowerShell modules and scripts to manage Windows hostsSecuring secrets and credentials with Ansible VaultDesigning repeatable automation workflows for provisioning and configurationTesting, debugging, and scaling automation for long-term maintainabilityCome ready to write YAML and PowerShell, fight with some whitespace in that YAML file, deploy servers, and leave with a repeatable framework for automating your own environment—whether it’s a homelab, a hybrid cloud setup, or an enterprise network.This workshop will be useful for IT Pros whether in their profession roles from help desk to Sysadmins, or even any homelab enthusiasts who wants to go beyond basic automation. No Ansible or PowerShell expertise is required, but some capacity for groaning at bad jokes is encouraged.