Modern IT feels stuck in a vicious cycle: software ships faster than ever, quality keeps slipping, and SysAdmins are left cleaning up the mess.

In this episode of SysAdmin Weekly, Andy Syrewicze and Eric Siron dig into the growing disconnect between developers and operations teams and why “good enough” software has become dangerously normalized across the industry.

We talk about brittle releases, missing error handling, forced beta testing in production, and how operational debt quietly drains time, money, and morale. From real-world outages and monoculture risks to AI hype, “vibe coding,” and the slow disappearance of software testing roles, this episode breaks down how we got here and why it’s not sustainable.

To be clear, this isn’t a developer-bashing session. It’s a reality check.

If software is going to keep the world running, it needs to be treated as a craft again, NOT a content pipeline. And that means shared accountability, better defaults, meaningful error messages, and respecting the people who have to run this stuff after it ships.

Episode Resources

- Cloudflare Outage - https://www.bleepingcomputer.com/news/security/cloudflare-blames-todays-outage-on-emergency-react2shell-patch/

- Satya Nadella Copilot skills challenge - https://www.youtube.com/watch?v=gBcwQaNoP5A

- SysAdmin Weekly Website - https://www.sysadminweekly.com

- SysAdmin Weekly Companion Newsletter - https://newsletter.sysadminweekly.com

- AndyOnTech - https://www.andyontech.com

- Project Runspace - https://www.projectrunspace.org

IT job postings have gotten… weird.

In this episode of SysAdmin Weekly, Andy flies solo to take a realistic look at modern IT job listings amongst historic industry layoffs and why so many of them feel disconnected from the actual work SysAdmins do every day.

We scroll through real-world postings, talk about unrealistic expectations, role creep, and “unicorn” requirements, and break down how vague or overloaded job descriptions contribute to burnout, churn, and impostor syndrome across the industry.

This isn’t a recruiter or HR dunk session. It’s a candid discussion about how job postings act as signals, why those signals are often confusing, and how both candidates and companies can do better by asking the right questions and setting clearer expectations.

Whether you’re actively job hunting, passively browsing, or just wondering who exactly these postings are written for, this episode is for you.

Episode Resources

- Anthropic Report on AI-Enabled Cyber Espionage

- IT Specialist Simulator

- SysAdmin Weekly - What Makes a Great SysAdmin?

- SysAdmin Weekly - Is University Worth it for Aspiring SysAdmins?

- Microsoft Learn - Discrete Device Assignment

- What are DMARC, DKIM, and SPF?

- SysAdmin Weekly Website

- SysAdmin Weekly Companion Newsletter

- AndyOnTech

- Project Runspace

Microsoft Ignite just wrapped and shockingly, it wasn’t only about AI.
(Okay, it was mostly about AI.)

In this episode of SysAdmin Weekly, Andy and Paul cut through the marketing noise and walk through what actually matters to SysAdmins from Microsoft Ignite’s Book of News. From AI agents showing up everywhere, to Azure resiliency, security posture management, and why massive cloud outages are still very much a thing. This is the practical, admin-focused breakdown you didn’t get from the keynote.

We dig into:

• What Microsoft’s push toward AI agents really means for control, governance, and security

• New Copilot and Azure features that might actually help… and a few that should make you cautious

• Why resiliency keeps failing at scale (and what Ignite quietly admitted about it)

• How Microsoft is trying to simplify security and management and where the complexity is just shifting instead

• The ongoing reality of cloud dependencies, outages, and shared responsibility

No hype. No sales pitch. Just two SysAdmins reacting honestly to what Ignite announced and what it means when the slides become production.

If you manage Microsoft environments, cloud workloads, or security policies, this one’s for you!

Episode Resources

- SysAdmin Weekly Website

- SysAdmin Weekly Companion Newsletter

- AndyOnTech

- Project Runspace

- Microsoft Ignite Book of News

- Paul Schnackenburg on LinkedIn

This week, Andy and Eric dive into one of the most underrated superpowers in IT: community. Not the cringe corporate “community,” but the real stuff. Think mentors, friends, people who help you level up, and the shared hive-mind that keeps SysAdmins alive during outages, zero-days, and career pivots.

From basements full of beige boxes to global open-source conferences, the IT world has evolved into something way more connected and way more essential than ever before.

Andy and Eric share personal stories from Microsoft MVP circles, KubeCon 2025, early career mentors, and the weird ways community quietly shapes your entire trajectory in tech.

In this episode you’ll learn:

- Why community is an actual career accelerator

- How mentors and advocates appear when you least expect them

- Why open-source communities operate differently than vendor ones

- Why contributing (even small stuff) builds reputation and opportunity

- Why community-first companies thrive.....and community-hostile ones decline

If you’ve ever wondered whether getting involved is worth it (spoiler: it absolutely is), this episode brings the stories, lessons, and laughs to prove it.

Episode Resources

- SysAdmin Weekly Website

- SysAdmin Weekly Companion Newsletter

- AndyOnTech

- Project Runspace

- Bank hit by audio deepfake scam

- Earlier SysAdmin Weekly episode on “enshittification”

Ready to leave password chaos behind? In this episode of SysAdmin Weekly, Andy and Eric break down the latest National Institute of Standards and Technology (NIST) password and identity-guideline updates and what they mean for you as a SysAdmin.

We cover:

- What changed and why (goodbye “special characters just because”)

- How to align your org with SP 800-63’s new structure and expectations

- Real-world tactics: from passkeys and token theft to legacy systems refusing to die

Also in this episode: bonus snark, smart home horror stories, PKI headaches, and identity as the new firewall

Whether you’re revamping your password policy or finally ready to ditch the “rotate every 90 days” mindset, this one’s for you.

Episode Resources

- SysAdmin Weekly website

- SysAdmin Weekly companion newsletter

- AndyOnTech

- Project Runspace

- NIST Digital Identity Guidelines (SP 800-63 suite)

- NIST SP 800-63B “Authentication & Authenticator Management”

- Evilginx2 (GitHub repo for the MITM/phishing framework)

In this episode, Andy and Eric dive deep into one of tech’s ugliest trends, the ULTRA-Corporatization of once-great vendors all for the sake of excessive profit at the expense of the company and customers. From Intel’s fall from grace to Dell’s support horror stories and VMware’s Broadcom-induced meltdown, the guys unpack how innovation-driven companies lose their soul chasing shareholder dollars.

They trace the full "life-cycle" of this process, from scrappy startup to bloated monopoly and look at how these same behaviors are infecting SaaS and the MSP world. Along the way, expect a few spicy rants about Microsoft’s licensing labyrinth, ARM vs. x86, 47-day certificate rotations, and why SysAdmins now spend more time managing vendors than managing servers.

If you’ve ever screamed at an E5 SKU, cursed a firmware update, or watched your favorite tech brand go corporate zombie, this one’s for you.

Episode Resources

- SysAdmin Weekly Website

- SysAdmin Weekly Companion Newsletter

- AndyOnTech

- Project Runspace

Referenced in this episode:

- WSUS Remote Code Execution Patch (CVE-2025-59287)

- What Is Cloud Native? (Episode 25)

- Microsoft Learn: SharePoint Limits and Boundaries

- VMware Episode (Referenced)

- GitHub Copilot Episode

Welcome to the Halloween special of SysAdmin Weekly, where Andy, Eric, Paul, and Mike gather ‘round the flickering glow of their monitors to share true tales from the trenches, the ones that still haunt their uptime dreams.

From flooded data centers and cursed SAN swaps to Novell nightmares, rogue backup tapes, and the eternal terror of “it’s always DNS,” this episode dives into the real-life horror stories that only SysAdmins could survive.

Expect nostalgia, gallows humor, and a reminder that in IT, every scream has a log entry.

Grab your candy corn, dim the lights, and join us as we celebrate the season of outages, late-night restores, and phantom pings.

Because sometimes… the scariest thing in tech isn’t ransomware, it’s the guy who forgot to check the backups....

#####Episode Resources

- SysAdmin Weekly Website

- SysAdmin Weekly Companion Newsletters

- AndyOnTech

- Project Runspace

- Azure 15-Year Anniversary News – Microsoft vs AWS Revenue Comparison

- OpenAI Atlas Browser

- KQLBench – Test LLMs on Microsoft Kusto Query Language

- Novell NetWare (for the brave and nostalgic)

- OS/2 Warp (IBM Historical Reference)

- SharePoint Online Storage and Retention Best Practices

In this episode of SysAdmin Weekly, the crew tackles one of the most debated questions in IT: Is university still worth it for aspiring SysAdmins in 2025?

Joining Andy is a friend of the show, Clay, a newly graduated IT professional from the Netherlands who shares his journey from tinkering with PCs as a kid to landing his first SysAdmin role. Together, they unpack how well higher education prepares students for real-world IT and where it still falls short.

Listeners can expect an honest, grounded look at the difference between theory and practice in modern IT. The conversation covers:

- Whether university programs keep pace with the speed of tech.

- What parts of formal education still provide lasting value.

- How certifications, home labs, and real-world experience stack up against degrees.

- Clay’s early-career lessons, including his first big outage (spoiler: it *wasn’t* DNS this time).

- The timeless SysAdmin truths about troubleshooting, documentation, and learning by breaking things.

This episode bridges the gap between the classroom and the server room with a mix of humor, career wisdom, and a few painful flashbacks to subnet calculations. Whether you’re a student, a career-switcher, or a long-time admin wondering how the next generation is being trained, this one’s worth your time.

Episode Resources

- SysAdmin Weekly Website

- SysAdmin Weekly Companion Newsletter

- Email the show

- AndyOnTech

- Project Runspace

- Clay’s LinkedIn

- F5 Networks breach news article

- SolarWinds Supply Chain Breach