The PowerShell Podcast

Jake Hildreth, Principal Security Consultant at Semperis and Microsoft MVP, is back on the podcast fresh off a trip to PowerShell Conference Europe, where he and Andrew co-presented a session on securing PowerShell. Jake also gave his own talk on Stepper, his open-source module for building resumable, step-by-step scripts — a tool that's grown considerably since his last appearance on the show. The two dig into what makes PSConf EU such a standout event, the refreshing lack of elitism in the PowerShell community, and the updates Jake's been shipping, including named steps, built-in logging, and secret suppression. The conversation winds into burnout, the importance of actually taking your vacation days, and how the same mindset that drives good automation — knowing when to stop and reset — applies to taking care of yourself.

Key Takeaways:

• Stepper has gotten some meaningful quality-of-life updates since Jake last appeared on the show, including named steps, automatic logging, and the ability to suppress secrets from logs — making it more practical for real-world production scripts.
• PSConf EU punches above its weight as a conference experience: technically deep but genuinely welcoming at every skill level, with none of the elitism that can creep into security-adjacent events.
• Your vacation time is a benefit, not a backlog item. Jake makes the case that getting good at separating your work time from your off time isn't a soft skill — it's a sustainability practice.

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, he goes by "horse" in the PowerShell Discords.

Resource Links:

• Jake Hildreth's Website: jakehildreth.com
• Jake's GitHub: github.com/jakehildreth
• Stepper (Resumable PowerShell Scripts): github.com/jakehildreth/Stepper
• Locksmith (AD CS Auditing & Remediation): github.com/jakehildreth/Locksmith
• Locksmith 2 (Next-Gen AD CS Toolkit): github.com/jakehildreth/…
• PowerShell Conference Europe: psconf.eu
• PDQ Discord: discord.gg/PDQ
• The PowerShell Podcast on YouTube: https://youtu.be/Rqkuaeps_jM

Andrew sits down with Robert Prüst, a Netherlands-based Microsoft MVP, to geek out about Pester, AI-assisted coding, and the power of showing your work in the PowerShell community. Robert breaks down how Pester works as a testing framework (unit testing, integration testing, and mocking) and explains why testing is the key to trusting AI-generated code. They also dig into a Visual Studio Code extension Robert built for Azure DevOps, the conference culture around PSConf EU, and why community involvement matters as much as technical skill. The conversation wraps with some honest takes on imposter syndrome, learning in public, and the value of just getting started.

Key Takeaways:

• Pester isn't just for unit testing your functions -- it scales all the way up to testing live infrastructure, validating Azure environments, and serving as the backbone of security tools like Maester. The more you invest in it, the more useful it gets.
• AI-generated code needs a safety net, and Pester is exactly that. Testing gives sysadmins a way to verify what the code is actually doing, which is especially critical when you didn't write it yourself.
• Imposter syndrome is almost universal in this community, and the people who feel it most are often the ones learning the most. Getting into community spaces -- online or in person -- is one of the fastest ways to grow.

Guest Bio:
Robert Prüst is a Microsoft MVP and MCT based in the Netherlands, focused on PowerShell, Azure automation, and DevOps. He has around 24 years of professional IT experience and has been working with PowerShell since roughly 2012. Robert is a regular speaker at PSConf EU, blogs at powershellpr0mpt.com, and is active on GitHub under the handle powershellpr0mpt. He runs a custom Azure Engineer bootcamp course and contributes to open source projects including the AMBA and EPAC frameworks.

Resource Links:

•  Pester documentation: https://pester.dev
•  Maester: https://maester.dev
•  PSKoans: https://github.com/vexx32/PSKoans
•  PSConfEU: https://psconf.eu
•  PDQ Discord: https://discord.gg/pdq
• Connect with Andrew: https://andrewpla.tech/links
• Robert’s blog: https://powershellpr0mpt.com
• Robert on GitHub: https://github.com/powershellpr0mpt
• Robert on LinkedIn: https://www.linkedin.com/in/rprust/
• The PowerShell Podcast on YouTube: https://youtu.be/7Z2Pk0y2Xss

 

Dan Adams is a 13-year Microsoft 365 and SharePoint veteran who joined Andrew to talk about the often misunderstood world of SharePoint, the shift to Microsoft Graph, and his custom PowerShell module built which can assess and benchmark M365 environments. Dan breaks down why SharePoint gets such a bad reputation (spoiler: it's usually about who built it, not the platform), explains why "everything in M365 is SharePoint" isn't just a meme, and digs into how the Microsoft Graph API is changing the way admins interact with the platform. He also shares his experience going from longtime podcast listener to first-time guest, and closes with some honest advice about reaching out to people in the community.

Key Takeaways:

• SharePoint's bad reputation often comes from poor initial architecture, not the platform itself. Getting the information structure right at the start has downstream effects on everything from Copilot to Purview to legal compliance, and PowerShell automation is only as useful as the metadata you've set up to work with.
• The Microsoft Graph API is consolidating how everything in M365 is accessed. Where older APIs like the SharePoint client-side object model might count a batch of 100 items as 100 separate API calls, Graph treats that same batch as a single call, which is a meaningful difference for performance and rate limiting.
• Dan's custom PowerShell module (SP’r Smash Bros Automation) automates M365 permission extraction to produce security assessments against CIS benchmarks and Microsoft Secure Score. Built as a practical tool for consultants and admins, it delivers a fast, standardized baseline of a tenant's security posture, featuring an optional AI sidecar to instantly generate personalized remediation plans.
  
  Guest Bio:
  
  Dan Adams is a Microsoft 365 and SharePoint Architect with 13 years of M365 consulting experience. Leveraging deep SharePoint and strategic information architecture expertise, he has led teams to deliver over 40 Fortune 500 intranets across industries ranging from healthcare to the NFL. He is the architect behind multiple award-winning portals, including two Ragan "Best Overall Intranet" winners. Dan is also an AI enthusiast, an advanced PowerShell expert, and the creator of the custom "SP'r Smash Bros Automation" module for Microsoft 365.
  
  Resource Links:
• Dan Adams on LinkedIn: https://www.linkedin.com/in/dan-adams-10887650/
• Dan Adams on Github: https://github.com/sprsmashbrosautomation
• Connect with Andrew: https://andrewpla.tech/links
• PnP PowerShell: https://pnp.github.io/powershell/
• PDQ Discord Community: https://discord.gg/pdq
• The PowerShell Podcast on YouTube: https://youtu.be/OLsTaKC9GmM
• PowerShell Wednesday Playlist: https://www.youtube.com/watch?v=XQT8lrn8hhU&list=PL1mL90yFExsix-L0havb8SbZXoYRPol0B

Encore presentation: Lessons in Leadership from PowerShell Pioneers Jeffrey Snover and Don Jones 

In this encore presentation of the PowerShell Podcast from April 28, 2025, we sit down with two legends of the PowerShell world: Jeffrey Snover, the inventor of PowerShell, and Don Jones, bestselling author, teacher, and longtime PowerShell community builder. Recorded live at the PowerShell + DevOps Global Summit, this conversation is packed with personal insights, impactful moments, and the kind of storytelling that only Snover and Jones can deliver.  

 Key topics in this episode include:  

•  The origin stories of PowerShell and how Jeffrey and Don’s paths crossed at a pivotal moment.  

• The evolution of PowerShell as a scripting language, community, and ecosystem.  

• The importance of storytelling in tech, from teaching to team-building to leadership.  

• The shift from individual contributor to leader and how both hosts navigated that path with intention.  

• The power of community: real stories from users whose lives were changed by learning PowerShell.  

• Career advice for the next generation of IT professionals and community contributors.  

Along the way, we hear hilarious stories from the early days of PowerShell development, honest reflections on growth and failure, and powerful reminders that vulnerability, repetition, and kindness are core to success in any career. Whether you're new to PowerShell or a long-time community member, this episode is a true masterclass in leadership, learning, and legacy.  

Bio and links:  

Jeffrey Snover is the inventor of PowerShell, Microsoft Technical Fellow, and a legendary figure in the IT and DevOps communities. With a background in distributed systems, Jeffrey led the development of PowerShell to revolutionize system management and automation on Windows. Known for his visionary leadership and storytelling, Jeffrey has played a pivotal role in shaping modern IT practices. His work continues to inspire technologists around the world to build, share, and lead with intention and clarity.  

Don Jones is a bestselling author, speaker, educator, and one of the most influential figures in the PowerShell community. With decades of experience in IT, Don has written numerous foundational books on PowerShell, including Learn Windows PowerShell in a Month of Lunches. He co-founded the PowerShell + DevOps Global Summit and has mentored countless professionals through his teaching, writing, and leadership. Don is a passionate advocate for storytelling in tech, career development, and building inclusive communities that empower the next generation.  

Resource links:  

https://www.linkedin.com/in/jeffreysnover/  

https://www.linkedin.com/in/concentrateddon/  

https://www.linkedin.com/in/andrewplatech/  

https://www.powershellsummit.org/  

The PowerShell Podcast: https://pdq.com/the-powershell-podcast  

The PowerShell Podcast on YouTube: https://youtu.be/51w_lWFIfqU

 

 

Andrew sits down with Leo D'Arcy, cloud solutions architect and PSConfEU speaker, to talk certificates, PKI infrastructure, and why so many organizations get it so spectacularly wrong. Leo shares how a decade of consulting work in remote access solutions pulled him into the world of Active Directory Certificate Services whether he liked it or not, and how that hands-on experience turned into conference talks and a genuine specialty. The conversation covers the difference between self-signed certs and proper CA infrastructure, why code signing deserves more attention than it gets, and how integrating signing into a CI/CD pipeline is less painful than it sounds. They also get into the "developer-ization" of IT, the underrated value of consulting experience for career growth, and why communicating across teams is just as important as knowing your PowerShell.

 

Key Takeaways:

• Code signing through a CI/CD pipeline is a practical, scalable alternative to constrained language mode. By adding a signing step to your build process, you get cryptographic proof that scripts haven't been tampered with, without giving up flexibility in what you can run.
• Self-signed certificates are essentially the same as having no certificate at all. A proper PKI means having a chain of trust, a policy behind how certs are issued, and infrastructure that your organization actually manages and maintains.
• Technical depth only gets you so far. The people who advance in IT are the ones who can talk networking with network engineers, infrastructure with server teams, and business outcomes with leadership. Soft skills aren't a bonus, they're a multiplier.

Guest Bio:
Leo D'Arcy is a UK-based cloud solutions architect with nearly a decade of consulting background in Microsoft technologies, including Azure, remote access solutions, PKI, and Active Directory Certificate Services. He's a repeat speaker at PSConfEU and runs the Remote Access User Group community on Discord. He's currently focused on Azure landing zone architecture and large-scale PowerShell automation at a stakeholder advisory firm.

 

Resource Links:

• Leo on GitHub: github.com/ld0614
• PSConfEU: psconf.eu
• Leo on Bluesky: https://bsky.app/profile/leodarcy.bsky.social
• Leo on LinkedIn: https://www.linkedin.com/in/leodarcy/
• Connect with Andrew: https://andrewpla.tech/links
• Microsoft Remote Access User Group Discord: https://discord.aovpndpc.com/
• The PowerShell Podcast on YouTube: https://youtu.be/BidUaXtwUNM

In this episode, Andrew chats with Adriano Carollo at PSConfEU about community, PowerShell Universal, AI, and what happens when you stop lurking and start talking to people. Adriano shares how PowerShell helped him grow from sysadmin into web apps, automation, and open source-style contribution, while Andrew reflects on learning, AI, and why enthusiasm still matters.  

Key Takeaways: 
· Community accelerates growth. Adriano came to PSConfEU after hearing Andrew encourage listeners to engage, and the payoff was immediate. 
· PowerShell Universal can open unexpected doors. Adriano describes using it daily to learn web development concepts like JavaScript, HTML, and React through PowerShell. 
· AI is most useful when it supports learning instead of replacing it. Both Andrew and Adriano talk about using AI for research, syntax help, documentation, and personal workflows while still valuing hands-on problem solving. 

Guest Bio: 
Adriano Carollo is a Berlin-based system administrator and PowerShell enthusiast who uses PowerShell Universal daily. He is active in the PowerShell Universal Discord community and is exploring automation, web apps, self-hosting, and entrepreneurship. 

Resource Links: 

• PDQ Connect:https://www.pdq.com/pdq-connect/
• PowerShell Scanner for PDQ Connect:https://www.pdq.com/blog/the-powershell-scanner-has-arrived-in-pdq-connect/
• PowerShell Universal:https://powershelluniversal.com/
• PSConfEU:https://psconf.eu/ 
• PDQ Community Discord:https://discord.gg/pdq
• Adriano C. https://linkedin.com/in/adriano-c-501203213
• The PowerShell Podcast on YouTube: https://youtu.be/qLYqUF9gD9s

Recorded live at PSConfEU 2026, Andrew sits down with returning guest Miriam Wiesner, Senior Security Researcher at Microsoft, for a wide-ranging conversation on PowerShell security, cookie-based attacks, and the evolving threat landscape. Miriam walks through her two conference talks — one on Microsoft Teams session cookie hijacking (a follow-up to her 2025 Entra ID cookie talk, complete with Cookie Monster branding and actual handcuffs), and a joint session with Stéphane van Gulick on using Microsoft Defender's Live Response feature for incident investigation. The conversation also covers the current state of PowerShell security, why sophisticated attackers are moving away from PowerShell, and why defenders who haven't enabled script block logging and AMSI are leaving easy wins on the table. On top of the technical deep dive, Miriam and Andrew get into the human side of the conference community — nerves before presenting, imposter syndrome, and why showing up is already half the battle.

Key Takeaways:

• Cookie-based identity attacks are an active and growing threat. Microsoft Teams, SharePoint, and OneDrive share session cookies, meaning a single cookie theft can give an attacker broad access across your organization's collaboration tools — no re-authentication required.
• Sophisticated threat actors are moving away from PowerShell specifically because its security features work. Script block logging, AMSI, and Constrained Language Mode make PowerShell activity highly visible and detectable. If your org hasn't enabled these, you're handing attackers an easy path.
• Visibility beats prevention. You can't prevent what you can't see. Detection through proper logging is not a consolation prize — it's a core security strategy, and Microsoft Defender's Live Response feature gives teams a powerful way to investigate isolated endpoints without needing RDP or PowerShell remoting enabled.

Guest Bio:
Miriam Wiesner is a Senior Security Research Program Manager at Microsoft with over 15 years of experience in IT security, penetration testing, and security automation. She works on research behind Microsoft Defender and Sentinel and is the creator of widely used open source PowerShell security tools EventList and JEAnalyzer. Miriam is a sought-after speaker at major security and PowerShell conferences including Black Hat, PSConfEU, and MITRE ATT&CK Workshops. She's also the author of "PowerShell Automation and Scripting for Cybersecurity," published by Packt. Her conference speaker career started at PSConfEU 2018 and she's been a fixture of the community ever since.

Resource Links
Miriam's 2025 Cookies talk - https://www.youtube.com/watch?v=8xDcq0pPNPs
Book – PowerShell Automation and Scripting for Cybersecurity (Packt): https://www.amazon.com/PowerShell-Automation-Scripting-Cybersecurity-Hacking/dp/1800566379
Miriam on LinkedIn: https://www.linkedin.com/in/miriamwiesner
Miriam on X/Twitter: https://x.com/MiriamXyra
Miriam's GitHub (EventList, JEAnalyzer, and more): https://github.com/miriamxyra
Miriam's Website: https://miriamxyra.com
Connect with Andrew: https://andrewpla.tech/links

The PowerShell Podcast on YouTube: https://youtu.be/zxJOqcEwgWE

 

Frank Lesniak joins Andrew Pla for a wide-ranging conversation that covers Frank's newly minted Microsoft MVP status, his journey through PowerShell, and what it looks like to build a real presence in the tech community. Frank talks through the pipeline struggles that tripped him up early on, how his VB Script and object-oriented background made the shift to PowerShell's object model feel disorienting, and how AI has quietly changed the way he approaches scripting today. The conversation takes a thoughtful turn as Andrew and Frank dig into impostor syndrome, the value of conference speaking, and how showing up consistently in the community compounds into a career. Frank also shares an update on DuPage Animal Friends, the nonprofit he serves, which supports one of the country's highest-performing open-admission animal shelters.

Key Takeaways:

• The PowerShell pipeline is one of the most commonly cited stumbling blocks for newcomers, especially those coming from text-based scripting backgrounds. Learning to visualize what your objects look like at each stage of the pipeline, using tools like Get-Member, is a skill that pays dividends long term.
• Showing up at conferences and user groups, even when you feel underprepared, is how you build the reps that eventually make it feel natural. Frank's consulting background gave him a head start on presentation skills, and he's clear that no one is born polished.
• Community involvement and career growth are more connected than they might look from the outside. Engaging with people on GitHub, at events, and through open source creates a feedback loop that builds confidence and opens doors.

Guest Bio:
Frank Lesniak returns to The PowerShell Podcast, this time as a Microsoft MVP (Microsoft Azure, PowerShell). Frank is a Sr. Cybersecurity & Enterprise Technology Architect at West Monroe, where PowerShell runs through client work on corporate M&A: carve-outs, tenant-to-tenant migrations, identity consolidation, endpoint moves, and security posture improvement across Microsoft 365, Azure, Entra ID, Active Directory, Intune, Defender, and Windows.

Beyond consulting, Frank speaks at technical conferences, mentors first-time speakers, and publishes open-source PowerShell standards and tooling, including PSStyleGuide, GloryRole, and PSConnMon. His public work threads least-privilege identity, cloud role mining, cross-platform observability, and high-quality AI-assisted development through standards, automated tests, and automated code quality reviews.

Connect with Frank: https://linktr.ee/franklesniak
Connect with Andrew: https://andrewpla.tech/links
PSConnMon - PowerShell Network Monitoring - https://github.com/franklesniak/PSConnMon/
GloryRole - Automating Least-Privlege Azure and Entra ID Directory Roles - https://gloryrole.com
PowerShell Style Guide - https://github.com/franklesniak/PSStyleGuide
PowerShell Style Guide + Coding Agents Lightning Talk - https://github.com/devops-collective-inc/pshsummit26/tree/main/PowerShellStyleGuideForCodingAgentsAndHumans-Lesniak
Coding Agent Accelerator Template Repo (Coming Soon!) - https://github.com/franklesniak/copilot-repo-template
ProStateKit - the DSC v3-Intune Starter Kit - https://github.com/franklesniak/ProStateKit
ProStateKit Promotional Commercial - https://www.youtube.com/watch?v=cA5vMH522F0
macOSLab - Automating Legit macOS VMs - https://github.com/franklesniak/macOSLab
DuPage Animal Friends - https://www.dupageanimalfriends.org/
PDQ Discord: https://discord.gg/pdq
The PowerShell Podcast: https://www.pdq.com/resources/the-powershell-podcast/
Previous episodes with Frank Lesniak: https://powershellpodcast.podbean.com/?s=Frank+Lesniak

The PowerShell Podcast on YouTube: https://youtu.be/Eg-uEGaurmY