SysAdmin Weekly #16: Reality Checks and Root Causes

When AI hallucinates, sudo breaks, and even elephants crush your RAM.

⏩ TL;DR — This Week in SysAdmin Land

· Running on-prem LLMs gets real with Ollama

· Home lab talk and blueprints from Project Runspace

· PowerShell Select-Object deep dives

· Azure Hybrid Benefit for Linux explained

· A Study from OpenAI on LLM hallucinations

· The Jaguar ransomware story continues + sudo exploit headlines

· BookStack as a documentation MVP

This Week’s Insight(s) from Andy

This edition leans into a theme I’m calling “Reality Checks”. In this context that refers to the messy truth between our ideal architecture diagrams and what actually breaks in production. From AI hallucinations to credential leaks, active exploits, and big companies being breached, tech doesn’t always respect our boundaries. My note this week will tie those stories together and challenge you (and me) to stay humble, vigilant, and ready to adapt.

It’s funny that this edition also features podcast episodes that discuss lab build-outs and local LLM architecture discussions. It’s funny because I can think of several cases throughout my career where the architecture was initially made with assumptions but ultimately wasn’t the correct architecture in the end. One example that comes to mind is from when Microsoft RDS (Remote Desktop Services) was the new cool-kid on the block. The provider I was with at the time had been servicing a large customer who wanted to start leveraging the thin-client model and use co-located RDS services for end-users.

On-paper the architecture followed all Microsoft best practices and each RDS host was specced in a way that followed industry standards as well as those recommended by the customer’s business applications and developers. Well, it turned out that due to the way one of said applications consumed memory, it didn’t become clear what the full needed RDS host memory requirement was until switch to production. Even the software vendor claimed that all should be well on shared infrastructure like RDS. Spoiler alert…. it wasn’t. Even the small test sample prior to going live didn’t surface memory contention.

The result? Poor performance on launch day due to an unforeseen memory consumption issue. We had RDS servers crumbling under the weight of 3 to 4 times more memory usage per session than what the architecture called for. Needless to say, these systems were paging memory like crazy and performance was…. less than stellar.

The moral of the story? We can’t make assumptions and take vendor guidance at face value. Question everything and test everything. Challenge your own assumptions. Because at the end of the day, if you don’t, Murphey’s Law will challenge them for you…. and not usually in a way that you prefer.

And now… back to our regularly scheduled programming….

Latest on the SysAdmin Weekly Podcast

Running LLMs On-Prem with Ollama
Andy and Mike Nelson dig into what it looks like to host large language models in your own datacenter (or basement). They wrestle with resource demands, deployment strategies, use-cases, and integration headaches. If you’ve ever thought “AI → Cloud only,” this episode might shake your assumptions.

What You Missed on Last Week’s Episode of SysAdmin Weekly

Building a Home Lab on the Cheap
Andy and Eric walk through how to bootstrap a functional home lab without draining your bank account. From repurposed hardware to clever virtualization, it’s the kind of episode you revisit when your budget says “no upgrades this year.” Great lessons for both newcomers and seasoned admins alike.

Sneak Peek of an Upcoming Episode

SysAdmin Horror Stories (Coming Late October)
We’re stitching together a “hall of horrors” version of SysAdmin life, complete with outages, screw-ups, and lessons learned. Want your story immortalized? Send it to contact@sysadminweekly.com (shame optional). Be sure to anonymize as needed……just don’t leave the punchline out.

From Project Runspace

How to Build a Home Lab for Learning Server Administration
Eric’s post here is a companion to last week’s podcast: it breaks down physical vs. virtual choices, pitfalls to avoid, and how to structure a lab you’ll actually use. Think of it as your lab’s blueprint……don’t build blind.

Core Fundamentals

The Windows Boot Process
Here’s what actually happens when a Windows box powers on: first the Windows Boot Manager, then the OS loader, then resume loader (for hibernation/fast boot paths). All boot settings are tucked in the BCD, editable with bcdedit (or MSConfig for the less adventurous). Add in Secure Boot, Trusted Boot, and ELAM, and you’ve got multiple layers defending your system before the user even signs in.

Helpful Community Content

PowerShell Select-Object Deep Dive
Andrew Pla and Fred Weinmann dig into how Select-Object can be wielded for cleaner, more efficient pipelines. If your PowerShell scripts feel messy, this is the kind of polish you need.

Upgrade to Windows 11 25H2 via Intune
Joey Verlinden walks through using feature update policies in Intune to push 25H2. Its helpful if you manage many endpoints and want a smooth upgrade path.

Azure Hybrid Benefit for Linux Explained
Thomas Maurer and Shreya Baheti detail how you can bring existing Red Hat/SUSE subscriptions into Azure, cutting redundant licensing costs and potentially saving a boatload vs pay-as-you-go.

Other SysAdmin Content from Vendors and Official Publications

Why Language Models Hallucinate
OpenAI turns the microscope inward and explains how hallucinations arise from how models are trained and evaluated. The takeaway? Some hallucinations are baked into the design, not just sloppy inputs. Understanding this helps you build more resilient systems around AI outputs.

Security Headlines for SysAdmins

Jaguar / Land Rover Ransomware & Data Theft
Even massive firms get hit. Factories went offline, data was stolen, and initial denials gave way to a public breach. Lesson: size ≠ immunity.

Sudo Vulnerability Under Active Exploitation
The --chroot (-R) handling in sudo has a flaw being exploited in the wild. Local privilege escalation, bypassing sudoer rules — patch now, test quickly, and verify mitigation.

Tool of the Week

BookStack
A lean, self-hosted documentation platform built on Laravel. Supports WYSIWYG and Markdown editors, roles/permissions, and structured books/chapters. If you need a central place for runbooks or team docs, BookStack is a strong option without the overhead of massive wiki stacks.

Quick Win of the Week

Fire up a BookStack instance (Docker, VM, whatever), import one critical doc (onboarding, firewall rules, etc.), and force yourself to use it exclusively for one week. That tiny shift centralizes knowledge, surfaces gaps, and starts cracking down on siloed knowledge.

Fun Retro SysAdmin Fact

Back in the day, Microsoft’s BootVis was a tool for profiling and optimizing Windows boot performance. Now, we take near-instant VM boot and container snapshots for granted, but sysadmins still can’t resist chasing those milliseconds.

☕ Wrap-Up

That’s all for now. We’ve walked through AI realities, lab ambitions, boot internals, and real-world security failures. The disconnect between expectation and execution is where we earn our stripes. Stay grounded, stay skeptical, and never trust assumptions.

Don’t forget:
- Send your horror stories for October to contact@sysadminweekly.com - Share this newsletter with a SysAdmin peer
- Hit reply with your feedback, war stories, or what you’d like us to cover next

Stay curious,

Andy