SysAdmin Weekly

Andy Syrewicze and Eric Siron

Welcome to the SysAdmin Weekly Podcast, your go-to source for IT-related content tailored to busy system administrators in the trenches. Hosted by longtime sysadmins and Microsoft MVPs Andy Syrewicze and Eric Siron, this show dives deep into the challenges and solutions that matter most to sysadmins on any given day. From technical know-how to real-world insights, SysAdmin Weekly is dedicated to those tireless professionals who keep our digital world running. Tune in for relevant topics, expert advice, and engaging discussions to make your busy schedule a little bit easier.

  1. 5 DAYS AGO

    025 - What is Cloud-Native? (And Should You Care?)

    In this episode, Andy teams up with Microsoft expert and Aussie tech legend Paul Schnackenburg to break down the buzzword that’s haunting every IT strategy deck: Cloud-Native. Together, they unpack what it really means in a Microsoft ecosystem from ditching on-prem Active Directory and ConfigMgr to embracing Entra ID, Intune, and Autopilot. Along the way, they hit on real-world migrations, the trade-offs of control vs. convenience, and why hybrid identity might actually make you less secure. Expect analogies about Death Stars, cruise ships, and even the Magic School Bus, because of course they did. Whether you’re an MSP plotting your clients’ next move or an IT pro trying to future-proof your environment, this episode’s your field guide to surviving (and thriving) in a Cloud-Native world. NOTE: As a reminder, be sure to share your IT Horror stories with us! We’d love to share as many as we can during an upcoming Halloween episode! Episode Resources: - CVE-2025-32463 (Sudo vulnerability details) - CISA KEV Catalog (Known Exploited Vulnerabilities) - SysAdmin Weekly Episode 22 – IT Documentation (Referenced in comments segment) - SysAdmin Weekly Episode 3 – WSUS Deprecation Discussion - Azure Files Overview - Microsoft Intune Autopilot Device Preparation (v2) - Microsoft Universal Print - Windows Autopatch Overview - Azure Arc for Servers - PowerShell Summit Session: Secure Management of Secrets with Azure Arc (Referenced by Andy) - SysAdmin Weekly Companion Newsletter - Contact the show

    1h 10m

  2. 2 OCT

    024 - On-Prem AI with Ollama

    This week on SysAdmin Weekly, Andy is joined once again by Mike Nelson for a deep dive into the world of local AI. Together, they unpack Ollama and Open WebUI, exploring how SysAdmins can run large language models on-prem to unlock powerful workflows while keeping sensitive data in-house. From hardware setups (yes, even that dusty old GPU in your basement), to why privacy-conscious SysAdmins are moving workloads local, Andy and Mike cover it all. Along the way, they swap stories on home labs, Ubiquiti gear, Ghost CMS, Hugging Face models, and where open-source AI really shines. If you’ve ever wondered why you’d bother with local AI when ChatGPT is just a browser tab away, this episode lays out the practical sysadmin use cases, security considerations, and future of AI in the trenches. Episode Resources: - SysAdmin Weekly Companion Newsletter - AndyOnTech - Project Runspace - Ollama Models Directory - BookStack Wiki Software - Confluence Free Instance (Atlassian) - Hugging Face Model Hub - Awesome MCP Servers (GitHub curated list) - Previous SysAdmin Weekly Episode: “The Importance of IT Documentation” - Previous SysAdmin Weekly Episode: “Building a Home Lab on the Cheap”

    1h 2m

  3. 24 SEPT

    023 - Budget Home Lab Setup for IT Pros

    In this episode of SysAdmin Weekly, Andy and Eric dig deep into how to build a fully functional home lab without selling a kidney. We cover picking hardware on the cheap, virtualization (Proxmox, Hyper-V, etc.), managing storage, navigating Microsoft licensing, layering in free cloud tiers, network tricks, and the kind of “what if I push this button?” experiments that keep us awake at 2 a.m. Whether you’re starting from a pile of old PCs or trying to mix in cloud credits, this show gives you the blueprint, the trade-offs, and, most importantly, the sanity checks. In this episode: - How to stretch every dollar on lab hardware - When to go physical vs. virtual (or hybrid) - Proxmox tips, license workarounds, and pitfalls - Cloud free/low-cost tiers you can use for testing - Network, storage & routing hacks we swear by - Real talk about maintenance, scaling, and failures Episode Resources - SysAdmin Weekly Companion Newsletter - AndyOnTech - Project Runspace - Windows Server Eval - Proxmox Installation Guide - Azure Free Services / Free Tier - Azure Free Account / $200 Credit - Azure Free Services Documentation

    1h 5m

  4. 17 SEPT

    022 - Why IT Documentation Matters (Even if You Hate Writing It)

    Hey folks! Andy here, and in this episode of SysAdmin Weekly Eric and I answer the hard questions regarding the documentation we all put off, but secretly depend on.... whether we like it or not. In this episode we cover: - Why poor (or missing) documentation is the root of so many SysAdmin nightmares - War stories where “future you” had to clean up past you’s mess - Tools, templates, and mindset shifts to make living documentation actually .....live - Change control, accuracy, and how to trust what your docs say Whether you're flying solo or managing teams, this episode will give you ideas to start building docs you’ll thank yourself for later. Hit subscribe, ring the bell, and share this with someone whose servers are mysterious even to them. Let’s make documentation less boring, more usable, and fearless. Episode Resources: - SysAdmin Weekly Companion Newsletter - AndyOnTech Blog - Project Runspace - Incident Response Markdown Template - Greenshot Screenshot Tool

    59 min

  5. 11 SEPT

    021 - Microsoft Entra ID Conditional Access Explained

    This week on SysAdmin Weekly, Andy is joined by regular co-host Paul Schnackenburg for a deep dive into Conditional Access, the cloud-era identity firewall you could say? and a cornerstone of Zero Trust security in Microsoft 365 and the Microsoft Cloud. We cover everything from the basics of conditional access policies to the nuances of break-glass accounts, layered policies, and how to avoid locking yourself (and your entire org) out of Entra ID. Along the way, we touch on Microsoft’s security defaults, authentication strengths, and the role of risky sign-ins and user risk detection in identity protection. Paul and Andy also share war stories from the trenches: configuring fresh tenants, wrangling MFA requirements, and learning why documentation and backups of your conditional access policies matter more than ever. Plus, there’s plenty of SysAdmin banter on Intel’s decline, ARM’s dominance, and even foldable phones! If you’ve ever wondered how to design policies without creating chaos or how to modernize your security controls without overwhelming your users, this is the episode is for you. Episode Resources - SysAdmin Weekly Companion Newsletter - AndyOnTech - Project Runspace - Microsoft Security Defaults Overview - Microsoft Entra Conditional Access Documentation - Microsoft Identity Protection (Risky Sign-ins & Users) - Authentication Strengths in Entra ID - Meister.dev – Conditional Access Testing Tool - Meryl Fernando’s Conditional Access Documentation Tool - Podcast with Tarek Dawoud on Entra ID Architecture

    1h 3m

  6. 3 SEPT

    020 - Top Microsoft Skills that Every SysAdmin Needs

    Andy and Eric break down the actual Microsoft skills that move the needle with no fluff, and no buzzword salad. We hit the core Windows/AD fundamentals, the PowerShell magic you’ll use every day, and the cloud/M365 bits that keep modern shops sane. If you’re trying to level up without wasting cycles, this is your roadmap. What we cover (at a glance): - Identity & Directory - AD/Entra basics, Group Policy that won’t bite you later, hybrid gotchas - Automation - PowerShell patterns you’ll use forever (loops, pipeline, remoting, “please don’t run that in prod”) - Networking for Windows admins: DNS/DHCP sanity checks, practical troubleshooting, knowing when it’s actually the firewall - Microsoft 365 - mail flow triage, Teams/SharePoint survival skills - Security stack - Defender realities, Conditional Access guardrails, least privilege that people will actually follow, Just in time administration. - Azure orientation - VMs, storage, networking, Arc and what’s worth learning first - Career path - what to learn now vs. what to park for later, and which certs are signal vs. noise Bring coffee. Leave with a plan. And yes, a little snark, because ticket queues were meant to be mocked. Episode Resources - SysAdmin Weekly Companion Newsletter - AndyOnTech - Project Runspace - SysAdmin Weekly - 018 - What did Broadcom do to VMware? - SysAdmin Weekly - 014 - How SysAdmins can Showcase Value - SysAdmin Weekly - 008 - Getting Started with GitHub Copilot

    1h 3m

  7. 27 AUG

    019 - What Counts as a Security Breach (and What Doesn't)

    "Compromised." We throw the word around like everyone agrees what it means, but do we? This week, Andy and Eric dig into the many faces of compromise in a security context and why it’s not a simple definition In this episode: - What actually counts as a security compromise (and why the answer is “it depends”) - Full breach vs. partial breach: Does it even matter? - Why lateral movement should keep you up at night - Session token hijacking in M365 and why MFA isn’t a silver bullet - The Myth of the Green Matrix Terminal Hacker (aka Hollywood hacking nonsense) - How risk profiling and layered defenses can contain the blast radius - Real-world detection failures and the “10,000 alert problem” - Practical steps to tune logs, outsource monitoring, and avoid burnout 📬 Reminder! - You can subscribe to the SysAdmin Weekly Companion Newsletter (link below) or email your own security horror story to contact@sysadminweekly.com! Episode Resources: - SysAdmin Weekly Companion Newsletter - AndyOnTech - Project Runspace - SysAdmin Weekly 012 - Identity is the New Firewall - Evilginx (Reverse Proxy Phishing Toolkit) - Debian 13 “Trixie” Release Notes - Ghost CMS Overview

    54 min

  8. 20 AUG

    018 - What Broadcom Did to VMware (and Why SysAdmins are Furious)

    Broadcom’s acquisition of VMware has left the sysadmin community reeling. From gutting VMware’s workforce to skyrocketing license costs (1000+ percent increases in some cases), cease-and-desist letters for perpetual licenses (really?), and a collapse in customer support, the VMware we once knew is gone. In this episode of SysAdmin Weekly, Andy Syrewicze and Eric Siron dig into: - How Broadcom’s handling of VMware triggered massive customer backlash - Why small and mid-sized businesses (SMBs) are being pushed away - The licensing and pricing nightmare (including lawsuits from giants like AT&T and UnitedHealthcare) - Declining customer experience and security patch transparency - Alternatives on the rise: Hyper-V, Proxmox, Nutanix - And even a spicy debate: will SysAdmins return to physical servers? If you’ve ever managed a VMware environment, are considering your virtualization options, OR you just need to share in VMware Grief, this one’s for you. Episode Resources: SysAdmin Weekly Companion Newsletter AndyOnTech Project Runspace Jen Easterly Joins Huntress Advisory Board

    58 min
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About

Welcome to the SysAdmin Weekly Podcast, your go-to source for IT-related content tailored to busy system administrators in the trenches. Hosted by longtime sysadmins and Microsoft MVPs Andy Syrewicze and Eric Siron, this show dives deep into the challenges and solutions that matter most to sysadmins on any given day. From technical know-how to real-world insights, SysAdmin Weekly is dedicated to those tireless professionals who keep our digital world running. Tune in for relevant topics, expert advice, and engaging discussions to make your busy schedule a little bit easier.

Information

  • Creator
    Andy Syrewicze and Eric Siron
  • Years Active
    2K
  • Episodes
    26
  • Rating
    Clean
  • Copyright
    © Andy Syrewicze and Eric Siron
  • Show Website
    SysAdmin Weekly

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