SysAdmin Weekly #15: Stories from the Trenches
Why the best SysAdmin lessons aren’t in manuals, they’re in the stories we live (and survive)
⏩ TL;DR — This Week in SysAdmin Land
· SysAdmin Weekly is moving to bi-weekly for deeper insights and less noise.
· New podcast episode digs into why documentation matters and how it saves your future self.
· Last week’s podcast broke down Conditional Access, including pitfalls, best practices, and lessons learned.
· Eric Siron shares tips on writing trouble tickets that actually get resolved.
· This week’s fundamentals spotlight is Linux basics, because cloud = Linux.
· Community voices highlight AI storage internals, running local AI agents, and Apple’s new disk image format.
· Apple preps macOS Tahoe with new fixes and updates for admins to tackle.
· Security headlines: worm-driven NPM supply chain attack and the Windows 10 support countdown.
· Tool of the week: Greenshot, the lightweight screenshot sidekick every sysadmin needs.
· Quick win: document one “failure mode” in your environment to save yourself later.
Schedule Change Announcement
SysAdmin Weekly - the Newsletter is going bi-weekly. Why? More value, less filler. This newsletter was always intended to be a supplement to the weekly podcast episodes and by doubling the time between issues, I can deliver insights and context instead of dumping a pile of links in your inbox. Quality over quantity…because your time is worth more than another unread newsletter.
NOTE: The podcast is our core content, and will remain (as always) on a weekly cadence!
This Week’s Insight(s) from Andy
This week ties together docs, tickets, lifecycle planning, and tooling. They’re not just chores they’re narratives. Documentation is the history book, tickets are the plot twists, OS lifecycles mark the chapters, and tools like Greenshot are the illustrations. Together, they tell the story of how systems live, break, and (hopefully) recover.
We’ve touched on learning in tech before, and I’ve found that storytelling, putting context around tech and solutions, is one of the most powerful ways to learn. Sure, the “cautionary tale” is classic IT lore, but there are also quieter stories worth telling: the “why do we do this” moments.
I think about the “why” a lot. Like when helping a nonprofit expand digital capabilities meant they could assist more people. Or when a medical customer’s patient database was down hard, and restoring it kept labs, imaging, and follow-up appointments running. Or in manufacturing, where IT-driven cost savings during a downturn literally kept entire teams employed.
Stories in IT aren’t just learning tools. They’re reminders of the very real human impact behind the job. So, the next time you’re buried in day-to-day sysadmin chaos, remember your “why.” Those stories you’ve lived? They matter.
And now… back to our regularly scheduled programming.
Latest on the SysAdmin Weekly Podcast
SysAdmin Weekly - 022 - Why IT Documentation Matters (Even if you Hate Writing it): Fresh episode just dropped today: Why Documentation Matters in IT. Eric and I talk about how documentation is your future self’s life raft, and that’s whether it’s recovery steps, config notes, or “who owns this service.” We share horror stories of missing docs causing chaos and give tips for making documentation suck less: structure, ownership, and findability.
What you Missed on Last Week’s Episode of SysAdmin Weekly
SysAdmin Weekly - 021 - Microsoft Entra ID Conditional Access Explained: Last week, Paul Schnackenburg joined me to dive into Conditional Access. What it is, why it matters, and where admins trip over implementation. We talked pitfalls (breaking workflows with too-tight policies), benefits (keeping accounts secure), and shared some real-world war stories. If you’re rolling out Conditional Access, this one’s your crash course.
Sneak Peek of the Next Episode
Coming up next week on SysAdmin Weekly: Building a Home Lab on the Cheap. We’ll be covering how to get started without draining your wallet. This includes hardware hacks, cloud freebies, and creative virtualization tricks.
I’d love to hear your homelab setups and stories. Share them with me, and I might feature a few in the show!
From Project Runspace
How to Submit an Effective Trouble Ticket - Eric shares some clear, actionable guidance on writing tickets that don’t get bounced around. Provide context, logs, what you tried, and what you expected. Better tickets = faster fixes and fewer headaches.
Core Fundamentals
Introduction to Linux (Linux Foundation Free Course)
Linux runs the world. This includes things like cloud workloads, containers, IoT, even your kid’s smart fridge. If you’re in IT and not comfortable on Linux, now’s the time. This free course gets you hands-on with the basics and helps you level up where it counts most.
Helpful Community Content
How Azure Storage Powers AI Workloads - Pierre Roman and Vamshi Kommineni explain how Blob Storage handles AI at scale. Storage isn’t just dumb disks anymore; it’s AI fuel.
Docker MCP Toolkit: Local Agentic AI Made Easy - Thomas Thornton breaks down running local AI agents with Docker’s MCP toolkit. Simplifies experimentation and orchestration for sysadmins tinkering with AI.
Apple’s New ASIF Disk Images - Howard Oakley benchmarks and explains who should care about Apple’s new format. If you deploy Mac images or deal with storage optimization, worth a read.
Other SysAdmin Content from Vendors and Official Publications
MacOS Tahoe Release Notes - New tweaks, fixes, and security updates. Admins managing Mac fleets should scan this closely for compatibility issues. Expect some patching fun and maybe a surprise or two in the UI changes.
Windows 10 End of Support - The end is near. If you’re still running Win10, plan upgrades now. Test legacy apps, drivers, and licenses before your helpdesk tickets explode.
Security Headlines for SysAdmins
Self-Propagating Supply Chain Attack Hits 187 NPM Packages - A worm-style exploit in npm packages. Mitigation tips: lock dependencies, use checksums, scan your supply chain, and restrict build agent permissions. Don’t let your CI/CD pipeline turn into a trojan horse.
Tool of the Week
Greenshot is Lightweight, open-source, and a sysadmin’s secret weapon for docs and tickets.
· Grab screen regions, windows, or even scrolling pages.
· Annotate, highlight, blur, and obfuscate sensitive bits.
· Export directly to clipboard, files, or email.
Greenshot is faster than Windows’ built-in tools and makes documenting issues painless.
Quick Win of the Week
This week’s theme is Infrastructure as Storytelling. Quick win: Pick one critical service and document its “failure story.” Who gets notified? What breaks? How do you fix it? Run the drill once and you’ll thank yourself when the lights go out.
Fun Retro SysAdmin Fact
SysAdmins in the ’80s swapped patches and tools on dial-up BBSs. Picture sitting by a phone line, listening to screeches, and praying no one picked up the phone mid-download. Kids today will never know the pain of a 2-hour patch download interrupted by mom making a call.
☕ Wrap-Up
That’s it for this round. Thanks for reading and keeping the lights on in IT.
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Stay caffeinated, stay patched, and stay sane.
- Andy