Autonomous IT

Maddie Regis speaks with Tom Bowyer, Director of Security at Automox, about the intersection of IT and cybersecurity. Tom shares his career journey, the importance of collaboration between IT and security teams, and insights into SOC compliance reports. He emphasizes the need for transparency, experimentation, and proactive problem-solving in enhancing cybersecurity. 

This episode originally aired October 17, 2024

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.

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.

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.

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.

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 

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.

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. 

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

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