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Jim Tyler is back for his third visit to the PowerShell Podcast, and he showed up with a full bag of new projects. Andrew and Jim dig into the PowerShell Engineer Standard, Jim's effort to get AI tools writing PowerShell the way a seasoned engineer would. What started as a Chrome extension idea for teachers turned into an AGENTS.md and CLAUDE.md standard, browser extensions, a VS Code extension that loops in PSScriptAnalyzer, and even a lightweight local model on Hugging Face so you can generate quality PowerShell without burning tokens. From there the conversation gets real about security in an agentic world. Jim talks about why local models matter for K-12 data privacy, why open weight coding models with no guardrails keep him up at night, and why small misconfigurations are now legitimate attack paths when an agent can probe your environment in seconds. He also shares how he has used PowerShell and AI to build audit tooling for Google Workspace that simply didn't exist before. The episode closes on the heart stuff. Jim walks through Model Communicator, the free AAC app he built with speech-language pathologist Kara Cotter to give nonverbal kids a voice without the $300 price tag or the months-long insurance wait. Plus a shout out to Jorge Suarez and endpointjobs.dev, the evolution of PowerShell.News and its new Repo Roundup, Jim's rebranded K-12 Engineer YouTube channel, and his "imposter to presenter" message that everyone has something worth sharing. Key Takeaways: Good AI output starts with good guardrails. The PowerShell Engineer Standard bakes in best practices like advanced functions, CmdletBinding, splatting, and version awareness up front, so you aren't fixing the same mistakes after the fact. Agents have changed the threat model. Misconfigurations that used to feel obscure are now real attack paths, which makes zero trust, process controls, and regular audits more important than ever. AI lowers the barrier to building meaningful tools, but expertise still matters. Model Communicator works because a speech-language pathologist hand-touched every board, and Jim still reads and understands the PowerShell his tools produce. Guest Bio: Jim Tyler is the Director of Technology at Niles Community Schools in Michigan, a Microsoft MVP, and the creator of PowerShell.News and PowerShellEngineer.com. He is the author of PowerShell for Systems Engineers and an elected school board member. Alongside speech-language pathologist Kara Cotter, Jim co-created Model Communicator, a free AAC app for nonverbal learners. He shares PowerShell, security, and AAC content on his YouTube channel, K-12 Engineer, and is a regular speaker in the Michigan K-12 tech community, where he encourages first-timers to go from imposter to presenter. Resource Links: PowerShell Engineer: powershellengineer.com PowerShell Engineer Firefox extension: addons.mozilla.org/en-US/firefox/addon/powershell-engineer PSEng model on Hugging Face: huggingface.co/jimtyler/pseng-14b-preview PowerShell News: powershell.news Model Communicator: modelcommunicator.com Endpoint Jobs: endpointjobs.dev PSScriptAnalyzer: github.com/PowerShell/PSScriptAnalyzer CISA ScubaGoggles: github.com/cisagov/ScubaGoggles Locksmith: github.com/jakehildreth/Locksmith Maester: maester.dev dbatools: dbatools.io PowerShell is fun (Harm Veenstra): powershellisfun.com ThreatLocker: threatlocker.com PDQ Discord: discord.gg/pdq The PowerShell Podcast on YouTube: https://youtu.be/gMUhzfLVchM

It's the Halloween episode, and Jake Hildreth is back to raise the dead. Fresh off Wild West Hackin' Fest in Deadwood, South Dakota (a town of 1,100 people that welcomes 1,200 hackers, a mechanical bull, and a round of Hacker Feud), Jake walks Andrew through his talk. The talk idea is simple and kind of brilliant: one tool to build a vulnerable AD CS lab, one tool to attack it, and one tool to defend and fix it. He also shares the very real story of ripping the auto-pwn pieces out of ESCalator four days before the talk and finishing his demos 45 minutes before showtime. Then things get spooky. Jake explains "zombie certificates," a persistence risk he uncovered while feeding RFCs and open spec docs into an LLM-built wiki and hunting for mismatches. A single registry value meant for testing and troubleshooting flips certificate revocation checking from fail closed to fail open. Pair that with the CA's disable extension list, strip the CRL address off a certificate, and you've got a cert you can revoke all day long that still lets an attacker walk right back in. The good news is the fix is straightforward hygiene. Along the way, Jake and Andrew talk about the full circle moment of thanking the person who got Jake into AD security, why sharing what you learned yesterday matters, and how a little mentoring can change someone's whole career path. Key Takeaways: Testing settings have a way of becoming permanent. A registry value meant for troubleshooting smart card logon can quietly turn certificate revocation into a fail open situation, so audit your domain controllers for it and only use it when you're actively testing. Certificates that can't be checked can't be killed. Keep the CA's disable extension list clean and make sure revocation info stays on your certificates, or revoking a compromised cert may do absolutely nothing. Learn it, then teach it. Jake turned years of AD CS work into tools, talks, workshops, and courses, and the people he's helped are now paying it forward with content of their own. Guest Bio: Jake Hildreth is a Principal Security Consultant at Semperis, a Microsoft MVP in both PowerShell and Identity/Access, and a recovering sysadmin with 25 years of IT under his belt. He's probably best known for building Locksmith, the open-source AD CS auditing and remediation tool, but he's also the creator of Stepper, Deck, BlueTuxedo, and PowerPUG! — a suite of tools designed to make identity security a little less painful for the admins who live in it. When he's not untangling Kerberos or chasing down ADCS misconfigurations, and can usually be found saying ridiculous things in the PDQ Discord's #off-topic channel. Resource Links: Battling Zombie Certificates: The Persistent Risk Lurking in AD CS (Semperis blog): https://www.semperis.com/blog/how-to-battle-zombie-certificates-persistent-ad-cs-risk/ Jake Hildreth's Website: https://jakehildreth.com Jake's Blog: https://blog.dotdot.horse Jake's GitHub: https://github.com/jakehildreth ADCSGoat (Deliberately Vulnerable AD CS Lab): https://github.com/jakehildreth/ADCSGoat ESCalator (AD CS Issue Combination Finder): https://github.com/jakehildreth/ESCalator Locksmith (AD CS Auditing and Remediation): https://github.com/jakehildreth/Locksmith Wild West Hackin' Fest: https://wildwesthackinfest.com Hybrid Identity Protection Conference (HIP Conf): https://www.hipconf.com CodeMash: https://www.codemash.org PDQ Discord: https://discord.gg/pdq Andrew's Links: https://andrewpla.tech/links The PowerShell Podcast on YouTube: https://youtu.be/ik4hlES4Uwc

Fresh off a PowerShell Wednesday session on Windows PowerShell versus PowerShell 7, Andrew Pla sits down with Ryan Yates, a longtime pillar of the UK PowerShell community and member of three PowerShell Working Groups (Cmdlets, Engine, and Interactive UX). Ryan pulls back the curtain on what working group members actually do, from triaging issues and reviewing PRs to deciding how bugs and enhancements should be implemented before the community picks up the work. The conversation rewinds to Ryan's early days as an IT apprentice at Barclays, where supporting SharePoint without a Visual Studio license led him straight to PowerShell and a lifelong love of breaking things to learn how they work. Ryan also shares his take on PowerShellGet and PackageManagement headaches, why PSResourceGet and DSC v3 point to a better future, how AI's cost barrier affects everyday PowerShell users, and his dream of turning old devices into a local AI compute farm. Things wrap up with a rapid-fire lightning round covering underrated cmdlets, favorite automatic variables, the most rewritten code block in PowerShell history, and a heartfelt call for more community eyes on the PowerShell repository. Key Takeaways: The PowerShell Working Groups triage issues and decide how bugs and enhancements should be handled, which opens the door for community members to step in and contribute the actual code. PSResourceGet (Install-PSResource and Find-PSResource) is the path forward for module management, and cross-platform software installation is shifting toward DSC v3 rather than PowerShell itself. Anyone can contribute. Start a discussion or open an issue in the PowerShell repository, and the team can convert between the two as needed. Everyone made their first contribution at some point. Guest Bio: Ryan Yates is a UK-based PowerShell community member who has been a driving force behind the UK and international PowerShell communities for over a decade. A former seven-time Microsoft MVP for PowerShell, Ryan currently serves on the PowerShell Cmdlets and Modules, Engine, and Interactive UX Working Groups, where he is in the PowerShell repository triaging, testing, and contributing. He began his career as an IT apprentice at Barclays supporting SharePoint, which led him to PowerShell, and he went on to help organize UK PowerShell user groups and PSDay UK. Ryan also helped keep the PowerScripting Podcast running in its later years. You can find him most days in the PowerShell Discord as pwshdoodUK. Resource Links: Ryan on GitHub: https://github.com/kilasuit Sponsor Ryan on GitHub: https://github.com/sponsors/kilasuit Ryan's Blog: https://blog.kilasuit.org/ Ryan on LinkedIn: https://uk.linkedin.com/in/ryanyates90 PowerShell Repository: https://github.com/PowerShell/PowerShell PowerShell Working Group Definitions: https://github.com/PowerShell/PowerShell/blob/master/docs/community/working-group-definitions.md PSResourceGet: https://github.com/PowerShell/PSResourceGet DSC v3: https://github.com/PowerShell/DSC ConsoleGuiTools (Out-ConsoleGridView): https://github.com/PowerShell/ConsoleGuiTools Microsoft.WinGet.Client Module: https://www.powershellgallery.com/packages/Microsoft.WinGet.Client PowerShell Discord: https://discord.com/invite/powershell PDQ Discord: https://discord.gg/pdq The PowerShell Podcast Hub: https://pdq.com/the-powershell-podcast The PowerShell Podcast on YouTube: https://youtu.be/r5IYrhIEH4Y

Andrew sits down with longtime PowerShell legend James Brundage to recap what he calls his "summer of fun," a stretch of side projects that prove PowerShell can go way further than most of us ever thought to push it. James kicks things off with Wave, a module for creating and manipulating real .wav files in the object pipeline. Once you see audio as a sine wave and some math, you can generate notes, play music, and even draw animated SVG waves straight from PowerShell. From there, the tour keeps rolling. MarkX turns Markdown into queryable XML so you can pull out code blocks or turn Markdown tables into typed data tables. James also shares how a vibe coded Wolfenstein 3D style clone in PowerShell (that got pulled from the internet after some tough feedback) sent him down the audio rabbit hole, and how he's collaborating with Bruce Payette on getting Braid to play nicely with PowerShell. Then it gets visual. James walks through his Matrix module, which brings the transformation matrices already baked into .NET over to PowerShell and CSS, and shows off a hallway of fake 3D depth built entirely with PowerShell generated SVG. He explains the simple trick behind PowerShell static sites (a .html.ps1 script that spits out HTML, plus a ToString or HTML property on your objects) and shares Fun, a tiny web server where any function named with a leading slash becomes a web page. The episode wraps with a promise of a Part 2, because there is clearly way more to cover. Key Takeaways: PowerShell can do a lot more than most of us assume. Audio waveforms, Markdown as queryable data, matrix transforms, and fake 3D graphics are all fair game once you understand the small piece of math or tech underneath. Static websites in PowerShell have been possible since version 1. Redirect output from a .html.ps1 script to a file, and add a ToString or HTML property to your objects so they render nicely on the web instead of dumping text in a terminal. With the Fun module, naming a function with a leading slash turns it into a route on a local PowerShell web server, which makes web experiments quick and low stakes. Guest Bio: James Brundage is a former Microsoft engineer and one of the most prolific PowerShell developers around, known through his company Start-Automating and the handle MrPowerShell. He is the author of a long list of open source modules, including RoughDraft for multimedia work with FFMpeg, and he founded the PoshWeb GitHub organization to bring together open source PowerShell web development projects. James is currently heads down on creative projects around PowerShell web development, audio, and graphics. Resource Links: PoshWeb GitHub organization (open to new contributors) https://github.com/PoshWeb Wave (work with wave files in PowerShell) https://github.com/PoshWeb/Wave MarkX (Markdown, XML, and PowerShell) https://github.com/PoshWeb/MarkX Matrix (matrix transforms with PowerShell, CSS compatible) https://github.com/PoshWeb/Matrix https://www.powershellgallery.com/packages/Matrix Fun (a fun functional PowerShell server) https://github.com/PoshWeb/Fun James Brundage on GitHub https://github.com/StartAutomating James Brundage's website https://MrPowerShell.com Previous PowerShell Podcast episode with Bruce Payette on PowerShell and Braid https://pdq.com/resources/the-powershell-podcast/ep-82-exploring-powershell-braid-and-beyond-with-bruce-payette The PowerShell Podcast on YouTube: https://youtu.be/WLEo6EjZqFM

Adam Driscoll, creator of PowerShell Universal, returns to the show for a deep dive into how AI has reshaped his day to day work. Since selling PSU to Devolutions last October, Adam has gone from writing thousands of lines of code himself to running a fleet of coding agents through GitHub Copilot, working across the PSU codebase, documentation, and Jira tickets. He and Andrew talk candidly about the personal side of that shift, the strange mix of mourning your old flow state while also getting more done than ever. From there the conversation turns practical, covering how Adam builds guardrails around agents using PowerShell modules and MCP servers, why planning in smaller steps beats one shotting a huge feature, and why Pester testing has quietly become non negotiable. They wrap with a PowerShell Universal 2026.3 update, including a redesigned admin console, new AI chat and MCP guardrail features, and Devolutions Agent support for running PSU jobs, plus a fun detour into Adam's side projects: a fully managed SQLite engine called Ahtola and an accidental 20,000 line Unity game. Key Takeaways: Treat your AI coding agent like a junior developer. It needs the "why" behind a task, not just the "what," or it will fill in the gaps with assumptions you don't want. Guardrails matter more as agents get more capable. Adam constrains what his agents can touch by routing them through well defined PowerShell functions and MCP tools rather than giving them free rein, and tool approval settings let IT admins do the same in more sensitive environments. Break big builds into small, reviewable steps instead of writing a massive plan and letting the agent run wild with it. Smaller steps mean you can actually review what changed at each stage. Guest Bio: Adam Driscoll is the creator of PowerShell Universal and joined Devolutions in October 2025, where he now leads its continued development. He's a longtime fixture in the PowerShell community, known for his tooling work and prolific output. Resource Links: https://ironmansoftware.com/ https://devolutions.net/ https://bsky.app/profile/adamrdriscoll.com https://discord.gg/PDQ The PowerShell Podcast on YouTube: https://youtu.be/u5zTzgEhWT8

Justin Grote (posh.guru) rejoins the PowerShell Podcast a year after his last appearance to talk about how fast the agentic AI world has moved since then. He walks through his experiments with the agent host protocol, running coding agents in isolated dev boxes and spot VMs so a stray command can only trash a container instead of his laptop. He and Andrew dig into what a "harness" actually is, how tools like these steer raw model output into something useful, and why that shift pushed Justin into a real existential dip this past summer, wondering what the point of hand building modules is when an agent can spin one up on demand. He works through how he came out the other side (doing it for the love of the game and the community), then gets into the practical stuff: a from-scratch C# rewrite of ModuleFast that cut Az module install time from seven seconds to three, the ExcelFast beta for slinging PowerShell objects in and out of Excel, and how he's tuning prompts using VS Code's new debug view and token caching. They also cover the rise of agent plugins (bundled skills plus MCP), his favorite lightweight plugin Ponytail, and Justin's read on where PowerShell fits once AI can talk to APIs directly. The conversation closes on advice for people getting into PowerShell right now and where to find Justin online. Key Takeaways: Agentic coding is moving fast enough that "harnesses" (the coordination layer around an LLM, like GitHub Copilot or Claude Code CLI) matter as much as the underlying model, and running agents in isolated dev boxes or spot VMs lets you hand over real autonomy without real risk. Feeling threatened by AI generating modules on the fly is common right now. Justin's answer was to keep building for the love of the craft and the community rather than chasing relevance. PowerShell's role is shifting from "the way you talk to a computer" toward a rapid prototyping and troubleshooting tool that both humans and AI agents reach for, especially anywhere a GUI or a full compiled language is overkill. Guest Bio: Justin Grote is a PowerShell MVP and the author of ModuleFast and ExcelFast, along with other tools in the PowerShell ecosystem like PoshNmap and several SecretManagement extensions. He works for a managed services provider and has been a fixture of the PowerShell community for years, known online as posh.guru. Resource Links: Justin Grote on GitHub https://github.com/JustinGrote Justin Grote on Bluesky (posh.guru) https://bsky.app/profile/posh.guru ModuleFast https://github.com/JustinGrote/ModuleFast ExcelFast https://github.com/JustinGrote/ExcelFast Ponytail (the agent plugin Justin mentioned) https://github.com/DietrichGebert/ponytail PowerShell Discord https://discord.com/invite/powershell The PowerShell Podcast on YouTube: https://youtu.be/MsgZoIKYnY0

Andrew welcomes back pen tester and AD security enthusiast Spencer Alessi (Tech Spence) fresh off DEF CON for a wide ranging chat on where PowerShell still fits into offensive security, how AI is changing his workflow, and what makes an environment genuinely painful to attack. Spencer talks through why PowerShell remains a favorite for both attackers and defenders, how he uses LLMs to speed up one off scripting tasks (and where they still fall short), and how he leans on AI tools to obfuscate offensive tooling during engagements. The conversation shifts into real world stories from the field, including a memorable case of exposed domain user hashes sitting on an overly permissive share, before wrapping up with the three controls Spencer sees make the biggest difference for defenders: application control, content filtering, and network segmentation. KEY TAKEAWAYS: PowerShell is still a top tool for both attackers and defenders because it is fast, flexible, and built into every Windows box, which is exactly why locking it down matters. AI is great for offloading quick one off scripting tasks, but it often assumes intent incorrectly and can produce messy code, so manual review and hand written scripting still matter. Application control, outbound content filtering, and network segmentation are the three controls Spencer sees make attackers' lives noticeably harder. GUEST BIO: Former Sysadmin, now Pentester @SecurIT360 | Microsoft MVP | Helping IT teams make their environment harder to attack | Social Media content & podcast @CyberThreatPOV RESOURCE LINKS: Spencer's website and newsletter: https://spenceralessi.com  Spencer's link hub: https://links.spenceralessi.com  Andrew's link hub: https://andrewpla.tech/links  SecurIT360: https://securit360.com  The Cyber Threat Perspective podcast: https://offsec.blog  PowerSploit (offensive PowerShell framework): https://github.com/PowerShellMafia/PowerSploit  Locksmith (AD CS misconfiguration finder, Spencer is a contributor): https://github.com/TrimarcJake/Locksmith  ScriptSentry (Spencer's logon script scanner): https://github.com/techspence/ScriptSentry  PDQ Discord community (PowerShell scripting channel): https://discord.gg/pdq  PowerShell Wednesdays (weekly livestream): https://www.youtube.com/@PDQ The PowerShell Podcast on YouTube: https://youtu.be/DDbBZqEJkSI

Andrew welcomes back Constantin Hager, a senior systems engineer, PowerShell User Group organizer, and brand new Microsoft MVP. They open by revisiting Constantin's infamous "size of a finger" intro from his first appearance, then dig into his talks at PSConfEU this year on dev containers with GitHub Codespaces and on Maester, the testing framework for M365 and on-prem AD. A quick detour into the GitHub vs. GitLab vs. Codeberg debate leads into the main event: a deep breakdown of Microsoft365DSC, what it actually does, how it treats M365 tenant settings like Intune, Entra, and Exchange as idempotent, drift-monitored code, and how the M365DSC Workshop wraps the notoriously painful setup process into a lab folder anyone can run. They cover the workshop's multi-tenant design, its DSC Community roots, and the honest limitations, like settings that still aren't exposed through public APIs. Constantin also shares his organic path to becoming an MVP, updates on his user group's shift to English-language talks, and a heads up on an upcoming blog series diving deeper into M365DSC. They close with news on the free PSConfEU MiniCon, happening October 13th with the CFP open until September 25th. Key Takeaways: Microsoft365DSC turns M365 tenant configuration into idempotent, drift-monitored code, and the M365DSC Workshop exists specifically to make the notoriously painful setup process approachable through a ready-to-run lab folder instead of a hundred-page whitepaper. Not everything in M365 is automatable yet. Settings without a public API (some Copilot controls, for example) still require manual portal fixes or an interactive token, so full automation has real gaps today. Constantin's MVP award grew out of years of showing up, organizing his user group, speaking at conferences, and opening GitHub issues, not out of being the loudest voice in the room. Guest Bio: Constantin Hager is a senior systems engineer based in Germany, organizer of the PowerShell User Group Inn-Salzach, and a newly awarded Microsoft MVP. A returning guest of the podcast, he's known for his enthusiasm around dev containers, PSFramework, and now Microsoft365DSC.   Resource Links: Constantin Hager on LinkedIn https://www.linkedin.com/in/constantin-hager/ Constantin's blog, The IT Guide https://the-itguide.de Andrew's blog: https://andrewpla.tech PowerShell User Group Inn-Salzach (Meetup) https://www.meetup.com/de-DE/powershell-usergroup-inn-salzach/ Maester (M365 and Entra security testing framework) https://maester.dev/ Microsoft365DSC official site https://microsoft365dsc.com Microsoft365DSC on GitHub https://github.com/microsoft/Microsoft365DSC M365DSC whitepaper and CI/CD pipeline scripts https://github.com/ykuijs/M365DSC_CICD DSC Community https://dsccommunity.org PSConfEU https://psconf.eu PSConfEU MiniCon Call for Papers (Sessionize) https://sessionize.com/psconfeu-minicon/ PDQ Discord https://discord.gg/PDQ The PowerShell Podcast on YouTube: https://youtu.be/Vy4kaayGT2M

David McFall joins Andrew Pla to talk about practical PowerShell, mentorship, automation, and why you do not need to be a PowerShell expert to get serious value from it. David shares how he uses PowerShell across Active Directory, Entra, Microsoft 365, Microsoft Graph, and PDQ, including real-world examples like device posture reporting, identifying hardware gaps, and automating project management. They also dig into learning with AI, knowing when a simple script is enough, the importance of testing before production, and why helping the people around you grow can make everyone’s job easier. Key Takeaways: · PowerShell does not have to be complicated to be useful. David approaches PowerShell as a working sysadmin who wants to automate repetitive tasks, reuse existing tools, and solve real problems rather than build everything from scratch. · AI can accelerate learning, but it should not replace understanding. David uses AI to better understand PowerShell concepts and Microsoft Graph, while emphasizing the importance of reviewing, testing, and understanding scripts before putting them into production. · Sharing knowledge makes the whole team stronger. David views himself as a mentor rather than simply a manager. Helping junior team members develop their skills gives them more opportunities while also creating a team that can share responsibility instead of relying on one person who knows everything. Guest Bio: David McFall is an IT infrastructure and operations leader with experience across enterprise cloud platforms, cybersecurity, system administration, Microsoft Defender, Azure, incident response, and automation. Based in Metro Detroit, David combines hands-on technical work with a strong focus on mentoring IT professionals and sharing what he has learned throughout his career. Resource links: ImportExcel (create Excel reports without Excel installed) https://github.com/dfinke/ImportExcel PSWriteHTML (build interactive HTML reports from PowerShell) https://github.com/EvotecIT/PSWriteHTML BurntToast (Windows toast notifications from PowerShell) https://github.com/Windos/BurntToast Maester (automated Microsoft 365 security posture testing) https://maester.dev The PowerShell Podcast on YouTube: https://youtu.be/36VN6K-oE8w

Andrew welcomes Morten Mynster back to the PowerShell Podcast to dig into the projects he’s been building around Microsoft Graph, Entra, least privilege, and authentication. Morten walks through Least Privileged Entra, a module that uses activity logs to identify users who may have more permissions than they actually need, and MS Graph Proxy, which lets developers work with mocked Microsoft Graph data locally without connecting to a live tenant. They also get into managed identities, the rougher corners of Microsoft 365 APIs, testing Graph-based projects in CI/CD pipelines, and how contributing to open source can solve real problems while creating unexpected career opportunities.   Key Takeaways: · Least privilege is easier when you can see what people actually use. Morten’s Least Privileged Entra module compares assigned Entra roles with activity data to identify permissions that may be unnecessary and suggest more limited alternatives. The goal is to give admins something actionable rather than simply reporting that a configuration passed or failed. · You don’t always need a live Microsoft 365 tenant to develop against Microsoft Graph. MS Graph Proxy intercepts Graph requests and responds with mocked data, allowing developers to test scripts and modules locally, offline, or inside CI/CD pipelines. It can also identify the minimum Graph permissions associated with the endpoints an application uses. · Sharing your work can have benefits far beyond the project itself. Morten credits his Least Privileged MS Graph project with helping him land his current job. His approach is simple: solve a real problem, share the solution, contribute where you can, and let other people build on what you’ve learned.   Guest Bio: Morten Mynster is an IT professional and open source contributor focused on Microsoft Entra, Microsoft Graph, security, and least privilege. His projects include LeastPrivilegedMSGraph, LeastPrivilegedEntra, and MSGraphProxy, and he regularly contributes to community projects and discussions around Microsoft 365 security and PowerShell. Resource Links: https://github.com/Mynster9361/Least_Privileged_MSGraph https://github.com/Mynster9361/LeastPrivilegedEntra https://github.com/Mynster9361/msgraphProxy https://github.com/FriedrichWeinmann/EntraAuth The PowerShell Podcast on YouTube: https://youtu.be/cB_QE1HvAyI

Mike Soule, Field CTO at Sentinel Technologies, returns to the PowerShell Podcast for the first time in three years to talk identity security, cloud configuration testing, and the evolving role of AI in the Microsoft ecosystem. Andrew and Mike dig into Maester, the open source PowerShell-based test automation framework that applies unit testing concepts to Microsoft 365 security configuration. Mike breaks down how Maester works, how Sentinel uses it with clients, and how the community has grown it into something that spans hundreds of built-in tests covering conditional access, CIS baselines, CISA standards, and more. They also cover EntraOps, the Enterprise Access Model, AI's impact on the MSP world, and why working in managed services is still one of the fastest ways to level up in IT. The episode closes with a strong Brandon Sanderson tangent. Key Takeaways: Maester brings the concept of unit testing to Microsoft 365 security configuration, letting admins continuously validate their cloud settings against known-good baselines with as few as three PowerShell commands. It's built on Pester, is fully open source, and now has over 100 community contributors. AI is changing the MSP landscape fast, but the fundamentals still matter. Mike and Andrew discuss how to think about Copilot licensing complexity, model routing in agent stacks, and why meeting users in their existing interface is often more important than deploying a shiny new tool. MSP experience accelerates learning in a way that internal IT often can't match. When you're working across multiple clients and environments, you accumulate reps quickly, and that breadth is hard to replicate elsewhere. Guest Bio: Mike Soule is the Field CTO at Sentinel Technologies, a large managed service provider focused on identity, cloud, and security strategy. Mike has been working hands-on with PowerShell, Entra ID, and Microsoft 365 security architecture for years and is a regular speaker at identity and security conferences. Resource Links: Maester (open source framework): https://maester.dev Maester on GitHub: https://github.com/maester365/maester Maester Cloud (hosted version by Merill Fernando): https://maester.cloud HIPConf (Hybrid Identity Protection Conference): https://www.hipconf.com EntraOps by Thomas Naunheim: https://github.com/Cloud-Architekt/EntraOps Mike Soule on LinkedIn: https://www.linkedin.com/in/mikesoule The PowerShell Podcast on YouTube: https://youtu.be/EQK693gGWoo

Andrew Pla sits down with TJ Turner at Microsoft’s TechMentor conference @ Microsoft HQ in Redmond, Washington, for a conversation about PowerShell, career growth, and the parts of working in IT that don’t show up in the documentation. TJ traces his path from infrastructure through K-12, finance, and retail to his current role as a Cloud Evangelist at TD SYNNEX, along with his early days using PowerShell v2 and v3, competing in the Scripting Games, and helping start the Philadelphia PowerShell User Group. They also dig into real-world automation wins, including a PowerShell workflow that helped validate thousands of systems before a holiday weekend, plus burnout, community, asking for help, and what years of broken demos and IT mistakes can teach you about staying prepared and learning to adapt. Key Takeaways: · What got you here won’t get you there. TJ’s career moved from hands-on infrastructure into distribution, cloud, and technical evangelism, and none of those moves were necessarily part of the original plan. Staying open to new roles, skills, and opportunities has been a big part of that growth. · PowerShell changes how you think, not just how you work. TJ shares examples of using PowerShell to validate thousands of systems, automate VMware update workflows, and collect detailed system state information. Over time, that automation mindset became part of how he approaches problems, even as his career moved beyond day-to-day infrastructure work. · Community and communication are technical skills too. Whether it’s recognizing burnout, asking for help, meeting someone at a conference, or admitting you don’t know an answer during a presentation, the ability to connect with other people can have just as much impact on your career as knowing the technology. Guest Bio: TJ Turner is a Cloud Evangelist at TD SYNNEX, one of Microsoft’s largest distributors in the CSP and partner channel. His background is in infrastructure, with experience spanning K-12, financial services, retail, and other enterprise environments. TJ got started with PowerShell during the v2 and v3 era, competed in the Scripting Games, and helped found the Philadelphia PowerShell User Group. Today, his work includes Azure, Microsoft 365, security, GitHub, DevOps, and helping partners grow their businesses. Resource Links: · TD SYNNEX Microsoft Partner Programs: https://www.tdsynnex.com/na/us/Microsoft/ · PDQ Connect PowerShell Scanner: https://www.pdq.com/powershell-scanner/ · PDQ PowerShell Scanner Blog Post: https://www.pdq.com/blog/the-powershell-scanner-has-arrived-in-pdq-connect/ · PDQ Community PowerShell Scanners Repository: https://github.com/pdqcom/PowerShell-Scanners · TJ Turner on LinkedIn: https://www.linkedin.com/search/results/people/?keywords=TJ+Turner+TD+SYNNEX The PowerShell Podcast on YouTube: https://youtu.be/ce9vxdkzDbo

Fred Weinmann is back, and this time he's walking us through the PowerShell Framework Collective – his personal answer to the age-old problem of building the tools that build the tools. The core idea is simple but powerful: if you invest in the scaffolding around your code, the actual code you write gets faster, cleaner, and more consistent every time. Fred breaks down four key wins from his framework stack, including PSModuleDevelopment for templating new projects, PSUtil for leveling up your console experience, PSReadLine for predictive history, and PSFramework itself for things like logging, configuration, parameter handling, and protected command execution. If you've ever spent more time wiring up logging and retry logic than solving the actual problem, this episode is going to feel very familiar – and very useful. Key Takeaways: PSModuleDevelopment makes spinning up a new, fully scaffolded PowerShell module a one-liner – complete with tests, GitHub release pipelines, and PowerShell Gallery publishing – so you can focus entirely on the actual functions you need to write. PSFramework handles the infrastructure layer of your code (logging, configuration, tab completion, parameter validation, retry logic) so you stop reinventing the wheel and your projects stay consistent across years and teammates. The real payoff of a shared framework is long-term maintainability: Fred opened a module he hadn't touched in six years and had a bug fixed and released in five minutes because everything was exactly where he expected it to be. Guest Bio: Friedrich "Fred" Weinmann is a Cloud Solution Architect at Microsoft and one of the most recognized PowerShell community contributors working today. He is the creator of PSFramework, which underpins many other modules in the ecosystem, as well as tools like PSModuleDevelopment, PSUtil, and the Active Directory Management Framework. Fred is a frequent conference speaker, a longtime community collaborator, and someone Andrew credits with helping shape his own PowerShell journey. Resource Links: PSFramework Project Home: https://psframework.org/ PSFramework on GitHub: https://github.com/PowershellFrameworkCollective/psframework PSModuleDevelopment on GitHub: https://github.com/PowershellFrameworkCollective/PSModuleDevelopment PSUtil on GitHub: https://github.com/PowershellFrameworkCollective/PSUtil PowerShell Framework Collective on GitHub: https://github.com/PowershellFrameworkCollective/ PDQ Discord – PowerShell Scripting Channel: https://discord.gg/pdq The PowerShell Podcast on YouTube:https://youtu.be/sZQdgBZM75Y

Andrew sits down with Evgenij Smirnov, a Berlin-based IT veteran with 30 years of experience in Active Directory and security consulting, to dig into what actually gets organizations popped. Evgenij walks through the most common escalation paths he sees in real-world AD environments, including over-permissioned accounts, exposed certificate authorities, and unencrypted domain controller backups, and explains how attackers chain these together to produce golden tickets and gain god-mode access. The conversation covers why these misconfigurations keep happening (bad defaults, lazy vendors, and a long history of "just click next"), how PowerShell fits into both hardening and attack scenarios, and what proper tier isolation actually looks like when you implement it with both authentication policies and user rights assignments. Evgenij also introduces his book, Building Modern Active Directory, and makes the case for treating security not as a chapter you can skip, but as something baked into the design from day one.   Key Takeaways: The most common Active Directory escalation paths are not sophisticated. Over-permissioned accounts with ACL chains to DC sync, exposed certificate authorities, and unencrypted backup tapes are consistently the entry points attackers exploit. If you can find these first, you are already ahead of most threat actors. Tier isolation done right requires both authentication policies and user rights assignment policies working together. Either technique alone leaves a blind spot that a determined attacker can walk through. Cybersecurity is a team sport, and bad cybersecurity is too. Microsoft ships AD with questionable defaults, vendors demand domain admin for service accounts, and administrators make shortcuts under pressure. The fix is not one heroic hardening sprint; it is a culture of least privilege built into every decision from the start. Guest Bio: Evgenij Smirnov is a Principal Solutions Architect at Semperis and a Microsoft MVP in both Security and PowerShell since 2020. Based in Berlin, Germany, he has spent more than 30 years in IT and security consulting, with deep expertise in Active Directory, identity security, and hybrid infrastructure. He is a longtime community leader, running the PowerShell User Group Berlin and the Windows Server User Group Berlin, and a regular speaker at conferences including PSConfEU. He is the author of Building Modern Active Directory, published by Apress in 2024.   Resource Links: Building Modern Active Directory (book site): ad2049.com Evgenij's personal blog): it-pro-berlin.de Evgenij on LinkedIn: linkedin.com/in/evgenijsmirnov ADMF (Active Directory Management Framework) on GitHub: github.com/ActiveDirectoryManagementFramework/ADMF ADMF documentation and project site: admf.one Attack Scenario To Go: https://github.com/HerrHoZi/AS2Go The PowerShell Podcast on YouTube: https://youtu.be/EQb7H6vBOtg

Andrew sits down with Fred Weinmann, one of the most prolific PowerShell module authors in the community, for part one of a multi-episode series covering his projects. This episode focuses on the Active Directory Management Framework, or ADMF, a configuration-driven system Fred originally built while working as a field engineer at Microsoft for a large enterprise customer managing hundreds of Active Directory forests. Fred walks through the problem ADMF was designed to solve: Active Directory is notoriously hard to manage consistently across environments, and most organizations just accept the chaos as the cost of doing business. The old approach at this particular customer involved zipping up scripts, RDPing into domain controllers, and running them manually. ADMF changed that by borrowing the test/apply concept from Desired State Configuration, but making it flexible enough to handle the messiness of real-world AD environments. The conversation covers how ADMF is structured around components (like organizational units) and contexts, why generating a reference configuration from an existing environment is harder than it sounds, the protocol juggling required to handle Group Policy and schema updates, and why Fred would use raw LDAP instead of the built-in AD commands if he were starting from scratch today. Fred also touches on the credential provider plugin system, which lets teams plug in their own password management workflows for things like break-glass accounts. Key Takeaways: ADMF follows a test-before-apply model borrowed from DSC, but trades DSC's all-or-nothing enforcement for a more selective, component-by-component approach that better fits the fluid reality of Active Directory management. Generating a configuration from an existing AD environment is tempting but potentially counterproductive. If you auto-generate your desired state from a domain that's accumulated years of cruft, you're not capturing what you want, you're just freezing what already exists. Performance at scale is a real consideration. The built-in Active Directory PowerShell module uses the AD Web Services protocol, which sends XML over the wire. Raw LDAP is significantly faster, and Fred says switching to it is the one architectural change he'd make if building ADMF over again. Guest Bio: Friedrich "Fred" Weinmann is a Cloud Solution Architect at Microsoft and one of the most recognized PowerShell community contributors working today. He is the creator of PSFramework, which underpins many other modules in the ecosystem, as well as tools like PSModuleDevelopment, PSUtil, and the Active Directory Management Framework. Fred is a frequent conference speaker, a longtime community collaborator, and someone Andrew credits with helping shape his own PowerShell journey. Resource Links: ADMF documentation and getting started guide: admf.one ADMF on GitHub: github.com/ActiveDirectoryManagementFramework/ADMF ADMF on PowerShell Gallery: powershellgallery.com/packages/ADMF PSFramework (Fred's logging, configuration, and scripting infrastructure module): psframework.org Fred Weinmann on GitHub: github.com/FriedrichWeinmann Fred Weinmann on X: x.com/FredWeinmann PDQ Community Discord: discord.gg/pdq   The PowerShell Podcast on YouTube: https://youtu.be/8SlIqUKP3hY