Go from monotonous to autonomous IT operations with this series. Hosts from Automox, the IT automation platform for modern organizations, will cover the latest IT trends; Patch Tuesday remediations; ways to save time with Worklets (pre-built scripts); reduce risk; slash complexity; and automate OS, third-party, and configuration updates on all your Windows, macOS, and Linux endpoints. Automate confidence everywhere with Automox.
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Automox Podcasts

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Automox Insiders – Curiosity, Adaptability, and Career Growth with Ryan Jeziorski, E13
11:39
11:39
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11:39In this episode of Automox Insiders, Maddie Regis speaks with Ryan Jeziorski, a Solutions Engineer at Automox, about the importance of IT adaptability and resilience. Ryan shares his diverse career background, his current role at Automox, and insights on how organizations can maintain uninterrupted services while adapting to changes in technology. …
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CISO IT — Hacker Summer Camp 2025: A Recap of Black Hat & DEF CON, E19
6:17
6:17
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6:17Join Automox CISO and SVP of Product Jason Kikta for a recap of Black Hat and DEF CON 2025. In this episode, Jason shares his take on the conversation around AI in cybersecurity shifting from hype to practical tools for defenders. Hear why integrating AI into your CI/CD pipeline, alert triage, and vulnerability management could be a game changer, p…
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Patch [FIX] Tuesday – August 2025: [Crafted Files, Spoofed Certs, and Good Ol' SQL Injection], E22
8:06
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8:06Join Automox cybersecurity experts Ryan Braunstein and Mat Lee for August 2025’s Patch [FIX] Tuesday, covering a Hyper-V privilege escalation, an Azure Virtual Machines spoofing flaw, and four serious SQL Server vulnerabilities. Learn how attackers could chain virtualization and cloud exploits, why crafted VHDX files and spoofed certificates are da…
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Hands-On IT – The State of IT Careers and the Role of AI with Forrest Brazeal, E11
14:44
14:44
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14:44In this episode of Hands-On IT, host Landon Miles sits down with special guest Forrest Brazeal to explore the current state of IT careers and the evolving role of AI in the tech landscape. As a renowned cloud architect and co-founder of Freeman and Forrest, Forrest shares his insights on upskilling for today’s competitive job market, the real impac…
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Automox Insiders – By Your Command: The Cybersecurity Directive with Tom Bowyer, E10
18:07
18:07
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18:07Maddie 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 enhan…
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Hands-On IT – A Prompt Engineering Deep Dive with Henry Smith, E20
34:04
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34:04In 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 sha…
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Product Talk – Alerting, Scheduling, and Smart Decisions, E19
11:17
11:17
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11:17Discover 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 decision…
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Heroes of IT – Sleeping Easier: Milton Webster’s Story of Risk Reduction with Automox, E18
13:50
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13:50In 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 proa…
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Autonomous IT, Live! Inside the Breach — Identity Hijack Response Exercise, E04
38:52
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38:52In 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.…
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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 cal…
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Automox Insiders – Customer Experience by Design: A Conversation with Kat Breeggemann, E18
22:29
22:29
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22:29In 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 …
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Patch [FIX] Tuesday – July 2025: [BitLocker Attack, Secure Boot Expiry, Linux chroot+sudo privesc, and Malicious .Zips], E21
21:29
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21:29In 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 es…
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Executive IT – The Art of Procurement: You Don’t Get What You Deserve — You Get What You Negotiate, E02
12:53
12:53
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12:53In 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…
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Automate IT – The Human Side of IT: A Toast to Sysadmins, E17
9:08
9:08
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9:08With 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 …
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Heroes of IT – Optimizing IT Workflows with Automox: Insights from Steve Engler, E06
11:17
11:17
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11:17Ashley 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…
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Product Talk – Procrastinators, Rejoice: Making the Windows 10 to 11 Migration Manageable, E18
11:31
11:31
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11:31Ready or not, Windows 11 is here. In this episode of Product Talk, Peter and Steph break down how IT teams can simplify the Windows 10 to 11 migration — without disrupting users or pulling all-nighters. From Worklets for readiness checks and silent upgrades to insights on hardware eligibility and inventory improvements, learn how to take control of…
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Automox Insiders – Ted Harapat, Tales of the Linux Firefighter, E03
13:49
13:49
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13:49In this episode of IT Insiders, host Maddie Regis sits down with Ted Harapat, Senior Systems Engineer at Automox, for a candid and compelling look into the world of Linux, cybersecurity, and the origins of IT careers. Ted shares how a midnight knock on his window sparked a decades-long journey into IT, what it’s like to support and expand Automox’s…
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Executive IT – Balancing Security, Usability, and Speed | E05
17:45
17:45
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17:45How can IT and the business work better together—without sacrificing speed, security, or sanity? In this episode of Executive IT, host Evan Kiely is joined by Volker Otto, a seasoned IT executive, to explore how teams can bridge the gap between user experience and technical requirements. They dive into the rise of business relationship managers, ma…
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Hands-on IT – Fostering Creativity in IT: Listen Monkey, Listen. E08
23:13
23:13
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23:13In this episode, Landon Miles interviews Jon Levenson, the manager of content and community at Automox, about the importance of creativity in IT and how to foster a creative environment. Jon shares his background as a former actor and how he fell into tech, as well as his experience in copywriting and podcast writing. They discuss the key elements …
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Patch [FIX] Tuesday – June 2025: [WebDAV Attacks, SSH Hijacks, and macOS Sandbox Escapes], E20
17:08
17:08
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17:08June’s Patch [FIX] Tuesday unpacks a lighter-than-usual Windows patch cycle — but don’t get too comfortable. Join Automox cybersecurity experts as they break down high-risk vulnerabilities across macOS and Windows, including: A chained SSH vulnerability (CVE-2025-26465 & CVE-2025-26466) that allows memory exhaustion and bypasses host key verificati…
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Hands-On IT – Making End Users Happy (and Maintaining Your Sanity), E19
8:08
8:08
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8:08Is tech easier than people? For many IT pros, the answer is a resounding yes. In this episode, Landon Miles tackles one of IT’s biggest challenges: managing user expectations while maintaining your own mental wellbeing. You’ll learn how to balance empathy with efficiency using proven frameworks like ITIL, SRE, and the NIST Cybersecurity Framework. …
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Automate IT – 5 Steps to Effectively Communicating with Your Executive Team, E13
9:24
9:24
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9:24In this episode of the Automate IT podcast, Jeremy Maldonado discusses the importance of engaging with executive teams and the necessity of clear communication within organizations. He emphasizes the value of understanding team dynamics, preparing effectively for discussions, and aligning goals with organizational priorities to foster collaboration…
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CISO IT – RSA 2025: Identity Is the New Threat Vector, E19
11:12
11:12
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11:12RSA 2025 revealed a shift: identity is now a primary threat vector in cloud security. In this episode, Jason Kikta breaks down the key takeaways from the conference—why identity has overtaken malware, how threat actors exploit service accounts and IDPs, and what this means for modern defense strategies. Plus, Jason shares observations on the evolvi…
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Product Talk – Simplified Patch Tuesday Scheduling & Beta Channel Controls, E17
16:28
16:28
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16:28In Episode 17 of Product Talk, Peter Pflaster and Steph Rizzuto walk you through the latest enhancements in the Automox console that help you work smarter — not harder. Discover how the new Agent Configuration settings let you choose between stable and beta release channels, control auto-upgrades, and manage endpoint behavior — all without submitti…
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Hands-On IT – 3 Tips to Make Your Endpoint Data Work for You, E18
5:42
5:42
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5:42In this episode of Hands-On IT, Landon Miles shares 3 tactical tips to help you make smarter decisions with your endpoint data. Learn how to cut through alert fatigue, streamline your reporting, and use historical insights to predict and prevent future issues. Whether you're managing a few hundred devices or thousands across mixed OS environments, …
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Automox Insiders – Data Trivia and Endpoint Truths, E17
22:15
22:15
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22:15In this episode of Automox Insiders, host Maddie Regis sits down with Peter Pflaster and Kelly Carlson from Automox’s product marketing team to explore how data transforms endpoint management. From mean time to remediate (MTTR) to device compliance and unexpected user activity trends, they break down the metrics IT pros should watch — and why clear…
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Executive IT – The Gatekeeper Myth: Why Procurement Is Your Biggest Ally, E04
14:01
14:01
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14:01Procurement is no longer just a gatekeeper — it’s a strategic driver in IT and security decisions. In this episode of Executive IT, host Evan Kiely sits down with Courtney Adams, a veteran procurement leader, to explore how smart procurement empowers better, faster, and more secure tech investments. From understanding true cost drivers to leveragin…
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Patch [FIX] Tuesday – May 2025: [Please Don’t Click That. Experts Review New Threats], E19
11:55
11:55
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11:55Mayday. Mayday. May Patch Tuesday? This month’s episode dives into four key Windows vulnerabilities you need to address — from scripting engine memory corruption in legacy Internet Explorer components to remote code execution risks in Remote Desktop and Visual Studio. Ryan Braunstein and Mat Lee unpack what each CVE means for your environment, how …
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Autonomous IT, Live! – Spring Into Automation: Clean Up Tech Debt & Refresh Your IT Operations, E03
34:18
34:18
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34:18In this episode of Autonomous IT, Live!, Landon Miles hosts leads a three-part discussion focused on spring cleaning your IT systems, workflows, and personal well-being. You’ll hear candid, practical insights from IT professionals tackling burnout, technical debt, and infrastructure hygiene head-on. This live show originally aired April 16, 2025 💼 …
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Teach IT – MFA Essentials: A Quick Guide for Everyone, E03
2:30
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2:30Think your password is enough? Think again. In this episode of Teach IT, we break down what multi-factor authentication (MFA) really is — and why it’s one of the smartest ways to secure your accounts. You’ll learn how MFA works, the difference between SMS codes, authenticator apps, biometrics, and physical security keys, and why phishing-resistant …
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Automate IT – Beyond the Spreadsheets: Asset Intelligence & Risk Scoring, E16
9:02
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9:02In 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 in…
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Hands-On IT – 9 Essential Spring Cleaning Tips for IT Pros, E17
9:12
9:12
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9:12Spring is in the air, and it’s time to give your IT environment the deep clean it deserves! In this episode of Hands-On IT, host Landon Miles shares nine essential spring cleaning tips to help IT pros declutter, optimize, and future-proof their systems. From cleaning workspaces and dusting off hardware to reviewing patch policies, auditing backups,…
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Automox Insiders – Tidy Endpoints, Tidy Mind: Spring Cleaning with Adam Whitman, E17
13:22
13:22
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13:22In this episode of Automox Insiders, host Maddie Regis chats with Adam Whitman, Manager of Solutions Engineering at Automox, about all things IT spring cleaning. From patch management and software audits to business continuity planning and endpoint hygiene, Adam shares practical, real-world tips for tidying up your tech stack and staying ahead of I…
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Heroes of IT – Casey Merritt’s Patch Playbook at Right! Systems, E17
14:52
14:52
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14:52In this episode, Ashley chats with Casey Merritt from Right Systems about how he manages patching and automation across both internal systems and MSP clients using Automox. Casey shares how he transitioned into IT, took ownership of Automox at his company, and now uses Worklets to streamline software removal, automate reporting, and reduce onboardi…
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Executive IT – Legal’s View on Tool Consolidation: Spring Cleaning Your Tech Stack, E03
15:15
15:15
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15:15Is your tech stack getting out of hand? In this episode, Automox General Counsel Paul Shoning joins Evan Kiely to unpack the legal and strategic risks of IT tool consolidation. From budgeting overlap to vendor lock-in, learn how to clean up your stack without making a mess.By Automox
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CISO IT – Reviewing, Patching, and Hardening: Decluttering Digital Infrastructure, E17
12:20
12:20
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12:20In this episode of CISO IT, host Jason Kikta explores the strategic value of digital spring cleaning—beyond just deleting old files. From uncovering forgotten network segments to tightening data retention policies, Jason walks through practical steps for reviewing your infrastructure, patching overlooked vulnerabilities, and hardening your environm…
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Product Talk – MTTR, CVEs, and What’s New in the Automox Console, E16
22:37
22:37
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22:37In this episode of Product Talk, Peter and Steph are joined by special guest Josh Kriese, Senior UX Developer at Automox, to dive into the latest product updates and design innovations. They cover the release of Automox Analytics, a powerful new reporting engine that introduces MTTR benchmarking and visibility into known exploited vulnerabilities (…
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Patch [FIX] Tuesday – April 2025: [Remote Desktop Roulette, CLFS Exploits, and macOS Vulns], E18
11:22
11:22
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11:22In April 2025's edition of Patch [FIX] Tuesday, the crew dives into April 2025’s patch highlights. Ryan kicks things off with a critical RDP Gateway vulnerability that requires no user interaction—just network access and bad intentions. Seth breaks down a kernel-level CLFS exploit that’s already been seen in the wild, while Henry shifts gears to Ap…
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Automate IT – Spring Cleaning with Automox: Clearing the Clutter, E15
16:24
16:24
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16:24In this episode of the Automate IT podcast, Jeremy Maldonado discusses the importance of cleaning and organizing your Automox environment. He emphasizes the need to optimize device management, remove disconnected devices, and improve policy performance. Jeremy provides practical tips on using Worklets, analyzing activity logs, and understanding pol…
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Heroes of IT – From Oregon Trail to IT Leader: Dustin Mobley’s Journey, E16
17:55
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17:55Ashley Smith chats with Dustin Mobley from SM Energy about how he got started in IT, how technology has changed over the years, and how his team uses Automox to keep server management under control. Dustin breaks down what it’s like managing a 24/7 server environment and shares real-world tips on building routines, working with business teams, and …
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Automox Insiders – Automating IT: How Breaking Servers Built a Career with Jeremy Maldonado, E15
22:12
22:12
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22:12In this episode of IT Insiders, Maddie Regis interviews Jeremy Maldonado, a Senior Solutions Consultant at Automox, discussing his journey with Linux in the web hosting industry. They explore the advantages of using Linux systems, the importance of creativity and balance in work-life, and the significance of the people behind technology.…
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Product Talk – Big Updates & Bigger Value: Your Sneak Peek Behind the Dev Curtain, E15
16:14
16:14
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16:14In this episode of Product Talk, host Steph Rizzuto and Josh Roland discuss the exciting new features coming to Automox, including a revamped end user notification system, enhancements to the device details page, new analytics for proving value, and improvements in remote control features. They emphasize the importance of customer feedback and the …
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Hands-On IT – The Titans of Server History: People, Rivalries, and the Machines They Created, E16
1:04:27
1:04:27
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1:04:27This episode dives into the fascinating evolution of server technology, from room-sized mainframes to today’s AI-powered cloud computing. It explores the innovations, rivalries, and key players—IBM, Microsoft, Unix pioneers, and the rise of Linux—that shaped the industry. The discussion covers the transition from minicomputers to personal computing…
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CISO IT – Dmitri Alperovitch’s Vision for Cyber Defense, E07
22:31
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22:31This episode originally aired on June 13, 2024. Join Jason Kikta as he interviews Dmitri Alperovitch, co-founder of CrowdStrike and author of World on the Brink. Alperovitch shares insights on the importance of speed in cybersecurity, the role of automation in IT management, and the rising threat of opportunistic cyberattacks. They explore how clou…
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Patch [FIX] Tuesday – March 2025: [Expert Analysis of Chromium, MMC, and VHD Vulnerabilities], E17
16:58
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16:58Tune in as Automox's cybersecurity experts break down the latest vulnerabilities from Microsoft's March Patch Tuesday release. This explores recent Chromium-based vulnerabilities, a significant Microsoft Management Console flaw, and file system vulnerabilities impacting VHD files. Beyond the technical analysis, the discussion highlights essential p…
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Automate IT – The Server Tango: Step In... and Now MySQL's Down, E14
12:40
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12:40In this episode, Jeremy Maldonado shares his experiences and insights on server management, highlighting the importance of learning from mistakes, the power of automation, and finding balance between Linux and Windows environments. He discusses the challenges and rewards of managing servers, the pivotal role of Ansible in streamlining operations, a…
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CISO IT – A Love Letter to Servers: Linux, Load Balancers, and the Architecture of Uptime | E16
9:15
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9:15In this episode of Automox's CISO IT podcast, host Jason Kikta delves into the world of servers, exploring their critical role in modern internet operations, the evolution of server technology, and the significance of Linux in the server landscape. He emphasizes the complexity of server management and the importance of reliability, highlighting how…
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Ever wonder why those software updates keep popping up? In this episode, we uncover how updates boost your security, introduce exciting new features, and keep your devices running at their best. Share it with friends, family, or coworkers who might feel overwhelmed by all things tech—help them stay safe and informed, too! Hosted by IT expert Landon…
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Product Talk – Inside Automox’s Approach to Third-Party Software Updates, E14
23:25
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23:25Peter Pflaster and Ben Glass team up in this episode of Product Talk to tackle the ins and outs of third-party application patching with Automox. They break down what third-party software means, where IT teams often struggle with patching, and why a centralized approach can make all the difference. With a relaxed yet informative style, the two cove…
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