Hey everyone! I’m not sure how I ended up missing this many weeks of the newsletter, but my apologies. Between work travel near every week for the past 5 weeks and getting knocked flat by whatever nasty cold / flu I picked up along the way, the newsletter went dark for too long. Thankfully the podcast had enough of a backlog built up that we could keep you fed there with regular content. So rather than wait until I’m caught up enough to write a full issue, I figured I’d share the episodes that went out since our last full edition of the newsletter.
NOTE: The newest podcast, Episode 063 with Eric on kernels and blue screens, just landed. I’m holding it for the next regular issue, so it gets a proper feature instead of a line in a roundup.
Below are the episodes we haven’t featured in a newsletter since I’ve been away. Additionally, I’ve paired each one with an older episode from the back catalog of the show that pairs well with it.
Hope you enjoy!
Episode 060: Microsoft 365 Licensing in 2026: What Changed and What It Costs You
Paul Schnackenburg teaches Microsoft 365 licensing to Microsoft partners for a living, which makes him the right person to ask why it keeps getting harder to follow. His answer, more or less: the complexity is deliberate, because that’s where the negotiating room lives.
Why it’s worth your time:
The July 1 increases landed on the SKUs small tenants live on. Business Basic went from $6 to $7 and Business Standard from $12.50 to $14, while Business Premium held at $22, which shrinks the gap that used to justify leaving people on Standard.
How a shop under 300 seats can buy most of what it wants from E5 through Defender and Purview add-ons on top of Business Premium, without buying E5.
What moved where this year: Intune Suite pieces folding into E3 and E5, features leaving E5 for the Entra Suite, and E7 showing up with Agent 365 attached.
The Monday action: line up your add-ons against your renewal date. If something you pay for separately just got bundled into your plan, nothing cancels the add-on for you.
Watch on YouTube:
Listen on Spotify
Pairs well with: Episode 018 - What Broadcom Did to VMware (and Why SysAdmins are Furious) - Eric and I on the other big licensing reset in this industry: price increases north of 1,000 percent in some cases, cease-and-desist letters to perpetual license holders, and the alternatives people started pricing out. It’s a year old now, and the lesson matches 060 from the other side of the stack. The terms are whatever the vendor says they are at renewal.
Episode 061: Why Does IT Burn People Out? SysAdmin Mental Health with Paul Croker
This is one of the most personal episodes we’ve recorded. Paul Croker founded 404 Stress Not Found because tech and cyber people had nowhere safe to talk about burnout, and he tells the story of the perfect storm that ended with him on a stage in Berlin telling his own. I talk about the MSP years that surfaced my generalized anxiety disorder.
Why it’s worth your time:
The line that stuck with me: we throw an alert when a disk hits 85 percent, and nobody has ever built the monitoring system for the person who gets the alert.
Hero culture and the all-nighter nobody questions, and Paul’s point that the all-nighter usually traces back to documentation that was never written.
What doesn’t work (a wellness app and a pizza) and what does: a community of people who do the same job, reached a lot sooner than most of us reach for one. 404 is free to join, runs meetups in the UK, and is open to anybody online.
Watch on YouTube
Listen on Spotify
Pairs well with: Episode 026 - Burnout in IT: Why So Many Tech Pros Are Struggling (and How to Cope) - If 061 is about why this industry breaks people, 026 is the practical half: imposter syndrome, always-on culture, notification overload, and what actually helps, from boundaries to managers who build psychological safety instead of putting it on a slide. It’s the one to forward to somebody who needs it more than you do.
Episode 062: What Free IT Training Actually Gets You Hired in 2026 and 2027?
Eric and I went through the free IT training worth your evenings, and the short version is that the training really is free. The exam that gets you past a resume screen is the part that still costs money.
Why it’s worth your time:
The free tier that holds up: Microsoft Learn, AWS Skill Builder, Cisco Networking Academy, and the Linux Foundation, plus the second tier nobody mentions, like IBM SkillsBuild, Salesforce Trailhead, and Google Skills.
What a Credly badge proves to a hiring manager. Mostly that you finished a module.
The guaranteed-pass pitch sitting in your LinkedIn DMs. A guaranteed CCIE means somebody is cheating.
How to turn free training into a callback: make your resume look like the person who already does the job you want.
Watch on YouTube
Listen on Spotify
Pairs well with: Episode 033 - Why IT Job Postings Are Completely Broken - Me, solo, scrolling through real postings: unicorn requirements, role creep, and job descriptions that read like four jobs stapled together. 062 is about getting your resume past the screen. This one is about who wrote the screen.
One Ask Before Halloween
We’re working on putting together a SysAdmin horror stories episode for Halloween. If you’ve got one, the outage that still wakes you up or the change window that went sideways at 2am, drop it in the comments or send it to contact@sysadminweekly.com. Names and employers stay out of it FYI.
The regular format comes back with the next issue.
Stay Frosty,
Andy
SysAdmin Weekly