Autonomous IT

The all-knowing IT pro is a myth. In this episode, Automox Senior Solutions Consultant Jeremy Maldonado breaks down why curiosity and asking for help are the real foundations of a successful IT career. He shares how he went from feeling nervous about asking questions to becoming a trusted resource for IT teams across industries, including hospitals, local governments, and school districts.

Jeremy also pulls back the curtain on what he does day to day on the Automox Professional Services team: reviewing IT admins' environments, evaluating patching schedules, and working collaboratively to fine-tune configurations. Rather than coming in as the all-knowing expert, he explains why the best results come from treating every engagement as a shared experience, where both sides learn from each other.

Whether you're early in your IT career or a seasoned admin, this episode is a reminder that growth starts with a question.

Topics covered:

- Why the all-knowing IT pro doesn't exist

- How curiosity drives career growth in IT

- What an Automox environment review looks like

- Tailoring patching best practices to different industries

- Finding room for improvement even when things work

NIST is falling behind on vulnerability scoring — and the gap is growing. In this episode, Peter and Steph break down what that means for IT and security teams relying on CVE data to prioritize patching, and how Automox is solving it.

We cover:

• Why NIST's National Vulnerability Database has a growing backlog and what's causing it
• How incomplete vulnerability data creates blind spots in your patch management program
• Automox's new partnership with VulnCheck to deliver real-time vulnerability intelligence
• What KEV (Known Exploitable Vulnerabilities) data is and why your leadership team cares about it
• Expanding from fewer than 10 third-party apps to 70% coverage across 500+ supported applications
• The rollout plan from third-party apps to macOS, Windows, and Linux

Whether you're running a mature vulnerability management program or just getting started, this episode lays out how the vulnerability data landscape is shifting and what you can do to stay ahead of real-world threats.

In this episode of Automox's Secure IT podcast, host Jason Kikta welcomes back Rich Casselberry, VP of IT security at AT&I, to discuss key insights from the CISO Blueprint. The conversation emphasizes the importance of a positive approach to security, the role of automation in IT practices, and the necessity of delegation to enhance efficiency. Rich shares real-world examples illustrating how a solution-oriented mindset can lead to better security outcomes and how automation can free up valuable time for IT professionals.

This episode originally aired January 16, 2025

February's Patch Tuesday includes two actively exploited vulnerabilities you need to patch now. Ryan Braunstein breaks down a denial of service flaw in Windows Remote Access Connection Manager that can black out your VPN infrastructure and leave remote endpoints unreachable. Seth Hoyt covers a pair of SmartScreen bypasses that let malicious files slip past Windows security prompts without warning.

Both vulnerabilities rely on user interaction to succeed, and phishing is getting harder to spot. Ryan and Seth discuss how AI is lowering the barrier to entry for attackers, making convincing phishing emails easier to generate and enabling single actors to operate like full teams.

What you'll learn:

• How attackers use VPN disruption as a distraction for larger attacks

• Why SmartScreen bypasses are a serious initial access vector

• Which endpoints to prioritize for patching

• How AI is changing the threat model for social engineering

Patch your systems. Train your users. Stay ahead.

In this episode of Automate IT, Jeremy Maldonado dives into the world of data-driven endpoint management, breaking down what it means to go “beyond the spreadsheets.” He explores how visibility, intelligent reporting, asset intelligence, and risk scoring can transform how IT teams manage and secure their environments.

Drawing from his own journey into the IT space, Jeremy unpacks practical strategies for improving compliance, prioritizing threats, and empowering IT teams to play offense, not just defense. Whether you're an IT pro or just endpoint-curious, this episode will give you fresh perspective on managing smarter, not harder.

This episode originally aired May 1, 2025.

In this episode of Automox Insiders, Maddie Regis welcomes back Charles Coaxum, SVP of Customer Experience at Automox, to talk about what really happens after the deal is signed. Charles shares a quick look at his career journey from frontline support to customer experience leadership, and explains why the moments that shape great leaders often come from the toughest customer conversations.

You will also get a first look at Charles’s upcoming podcast on the Automox network, where he plans to bring honest, practical stories from the post sale world without the extra polish. Then Maddie puts Charles through a customer experience themed would you rather game, covering big company wide issues versus lots of small problems, leading with smooth operations versus always jumping in to help, and choosing steady improvements versus bold changes.

If you are curious about how trust, accountability, and listening drive better outcomes for customers and teams, this episode is for you.

What if the IT industry stopped pretending everything is “fine”?

In this Autonomous IT live show, Automox CEO Justin Talerico shares candid perspectives on the real state of IT as the industry heads into 2026 — where things are breaking down, why burnout is becoming an operational risk, and what actually needs to change.

Topics include:
-- Why many IT careers begin with curiosity and stall under constant operational pressure
-- The operational risk created by manual work and hero-based infrastructure
-- Why automation initiatives fail and why the root cause is rarely the tooling
-- How IT leaders can rebuild trust in automation and autonomy
-- What IT leaders will look back on and question about endpoint management in 2025

The discussion concludes with a rapid-fire game:
AI vs Human vs Hybrid, deciding where IT work belongs in 2026.

This is not a product pitch.
It is not a trend report.
It is an honest conversation about how IT actually works today and how it needs to evolve.

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.

This episode originally aired July 29, 2025. 

Public Key Infrastructure (PKI) underpins nearly every secure interaction in modern IT, but it's also one of the most misunderstood and overlooked foundations of security.

In this episode of Secure IT, host Jason Kikta is joined by Mark Cooper, CEO and founder of PKI Solutions, to unpack why PKI is so critical to identity, authentication, and trust, and what happens when it fails.

They explore how certificates enable passwordless authentication, secure TLS connections, IoT devices, endpoints, and enterprise systems, while also examining why misconfigured or poorly monitored PKI environments often become an attacker's fastest path to privilege escalation. From certificate expirations and operational outages to real-world breach scenarios and pen test failures, this conversation maps the full PKI risk spectrum.

Jason and Mark also challenge a common assumption in cybersecurity: that recovery equals resilience. Instead, they argue that true resilience means staying secure and operational, even during misconfiguration, failure, or attack.

Whether you're new to PKI or responsible for running it, this episode will change how you think about identity infrastructure, resilience, and trust.

Topics covered:

- What PKI is and why most organizations already depend on it
- Certificates, passwordless authentication, and digital identity
- How PKI misconfigurations enable high-impact attacks
- Why recovery is the weakest form of resilience
- The hidden operational and security risks of foundational systems

Automox announces its new partnership with Splashtop, bringing secure remote control directly into the Automox console. Host Peter Pflaster is joined by Italo Nava from Splashtop and Automox Product Manager Steph Rizzuto on launch day to break down the integration and what it means for IT teams.

They discuss why remote access is still essential even when automation handles most of the work, the cost of switching between tools during urgent issues, and how Splashtop’s 20 years of experience drives reliability and security. Steph also shares early access results, including average connection times under 10 seconds and a 95% success rate.