Autonomous IT

Latest Episodes:

Hands-On IT – A Prompt Engineering Deep Dive with Henry Smith, E20 Jul 29, 2025

Show notes

In this episode of Hands-On IT, host Landon Miles is joined by Automox Security Engineer Henry Smith for a deep dive into prompt engineering and how it’s transforming the way IT and security teams work with AI.

From crafting high-quality prompts to auditing and hardening code using large language models like Claude and ChatGPT, Landon and Henry share real-world insights, practical strategies, and lessons learned from implementing AI in secure development workflows.

They also explore:

Why context is king when prompting AI
Security implications of AI-generated code
Tips for optimizing token usage and context windows
How Automox engineers are experimenting safely with AI

Whether you're a developer, security professional, or IT leader, this episode offers actionable advice and forward-thinking perspectives on integrating AI into your workflow.

Product Talk – Alerting, Scheduling, and Smart Decisions, E19 Jul 24, 2025

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Discover how Automox is transforming IT reporting. In this episode, Steph Rizzuto talks with product lead Emily Pace and engineer Ben Glass about new reporting features that give you real-time visibility, alerting, and automation. Learn how IT teams are cutting reporting time from 30 hours to 1, setting up custom alerts, and making smarter decisions—without logging into the console 24/7.

Heroes of IT – Sleeping Easier: Milton Webster’s Story of Risk Reduction with Automox, E18 Jul 22, 2025

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In this episode of Heroes of IT, Ashley sit down with Milton Webster to explore how his team transformed their IT operations using Automox. From reducing endpoint risk scores in record time to implementing automated Windows 11 upgrades with Worklets, Milton shares real-world wins and challenges from the frontlines of IT. Learn how a culture of proactive patching helped his organization boost security and sleep easier at night. If you're navigating risk management, remote device updates, or end-user satisfaction, this conversation is packed with practical insight.

🔧 Topics Covered:
• Endpoint security & patch automation
• Risk score reduction with Rapid7 & Automox
• Worklet-powered upgrades & scripts
• Reboot strategies that actually work
• Culture change in IT and user communications

🎧 Whether you're an IT leader, sysadmin, or tech strategist, this episode delivers actionable advice from someone who's been there.

Autonomous IT, Live! Inside the Breach — Identity Hijack Response Exercise, E04 Jul 17, 2025

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In this special live episode of Autonomous IT, Live! we walk through a high-stakes incident response drill that mimics a disturbingly realistic threat scenario: an attacker gains access to your internal tools — not by breaking in, but by logging in.

Here's the setup: a user unknowingly reuses compromised credentials with the company’s SSO provider. An attacker logs in, flies under the radar, and impersonates internal IT support using Slack, email, and calendar invites. Their goal? Convince employees to install a fake remote access tool—all while avoiding anyone likely to report suspicious behavior.

Join Landon Miles, Tom Bowyer, and Ryan Braunstein as they:

🔍 Investigate a suspicious login and Slack impersonation
🔐 Contain and remediate the breach using real-world tactics and tools
📉 Discuss phishing-resistant MFA, endpoint visibility, Slack impersonation risks, and more
🧠 Share tips on improving security awareness, incident playbooks, and interdepartmental collaboration
💬 Answer live audience questions about malware analysis, EDR response, and building detection rules

Whether you’re a security veteran or just starting out in IT, this episode offers an unfiltered look at how to respond when credentials are compromised and attackers act like insiders.

📎 Bonus: We also include a downloadable Incident Response Checklist to help your team run your own tabletop exercise.

🛡️ Because in today’s world, attackers don’t need to break in—they just need to log in.

CISO IT – The Automation Imperative, E10 Jul 15, 2025

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In this episode of Automox's CISO IT Podcast, host Jason Kikta returns from Black Hat and DEF CON in Las Vegas to discuss one of the most talked-about IT events of the summer, and what it truly reveals about automation in IT. Contrary to popular fearmongering, Jason argues that the incident isn’t a cautionary tale against automation but a clear call for more thoughtful automation.

Jason breaks down why automation, when paired with rigorous testing and strategic controls, is critical to modern IT and cybersecurity success. He challenges listeners to rethink what IT efficiency really means—not job cuts, but freeing teams to tackle the backlog and do more meaningful work. He wraps with a personal challenge: find and automate one tedious task this week using tools like Automox, Okta workflows, or your own scripts.

This episode originally aired September 12, 2024

Automox Insiders – Customer Experience by Design: A Conversation with Kat Breeggemann, E18 Jul 10, 2025

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In this episode of Automox Insiders, host Maddie Regis sits down with Kat Breeggemann, Digital Customer Experience Manager at Automox, to explore her unique journey from journalism and communications into the world of customer success. Kat shares how a leap-of-faith internship opened the door to a career in CX, the pivotal moment she advocated for her own role, and why scaling digital experiences is the key to supporting thousands of end users effectively.

You’ll learn:

What digital CX looks like in action
How to transition your skillset into tech
The importance of proactive, scalable customer education
Why assuming user knowledge can break your product experience
Career advice for new grads and professionals making a switch

Whether you're navigating your own tech career or building better customer journeys, this episode is full of practical insight and inspiring takeaways.

👉 Subscribe to the Automous IT Podcast for more behind-the-scenes conversations with the people shaping IT.

Patch [FIX] Tuesday – July 2025: [BitLocker Attack, Secure Boot Expiry, Linux chroot+sudo privesc, and Malicious .Zips], E21 Jul 08, 2025

Show notes

In this July 2025 Patch [FIX] Tuesday episode, Automox security experts Tom, Seth, and Cody unpack four high-impact threats — from Microsoft updates, to Linux vulns, and .zip exploit PoCs.

Topics include a physical attack method bypassing BitLocker encryption (CVE-2025-48001), the looming expiration of secure boot certificates, a Linux privilege escalation flaw in chroot and sudo (CVE-2025-32463), and a proof-of-concept .zip exploit that hides malicious content during preview but runs it on unzip.

Expect sharp technical insights, practical mitigation tips, and as always, a few laughs.

Executive IT – The Art of Procurement: You Don’t Get What You Deserve — You Get What You Negotiate, E02 Jul 03, 2025

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In this episode of Executive IT, host Evan Kiely and guest JB Snodgrass discuss the intricacies of procurement processes, effective negotiation strategies, the importance of timing and communication, and common pitfalls to avoid when evaluating tools. JB shares insights from his extensive experience in procurement, emphasizing the need for thorough research, stakeholder engagement, and strategic negotiation to secure the best outcomes for organizations.

This episode originally aired March 18, 2025

Automate IT – The Human Side of IT: A Toast to Sysadmins, E17 Jul 01, 2025

Show notes

With a newborn at home and fueled by coffee (and Linux), Jeremy reflects on what it means to support both technology and people. In this episode, Jeremy tackles some of IT’s toughest challenges — maintaining balance, fostering gratitude, and safeguarding your mental health.

Whether you’re rebooting servers at 2 am, automating backend workflows, or trying to catch your breath, this episode is for you.

Topics covered:

Balancing 2 a.m. server reboots with life at home | What that means for you
Spotting early burnout signs | Steps you can take now
Learning from peers | Practical tips to expand your IT skill set
Finding small wins | Why a quick acknowledgment goes a long way

Heroes of IT – Optimizing IT Workflows with Automox: Insights from Steve Engler, E06 Jun 26, 2025

Show notes

Ashley sits down with Steve Engler from the Oklahoma Farm Bureau to explore his journey from taking apart his first computer to becoming a certified Automox expert and system admin.

Stephen shares how he:

Transitioned from the Air Force into IT
Unlocked the full potential of Automox in a previously underused environment
Built a hands-on lab to test Linux and Windows automation
Earned all three Automox University certifications
Became a go-to expert through community collaboration and scripting

This episode originally aired July 21, 2024

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