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