Twenty years of Windows administration, a framed Windows 2000 certificate on the wall and a coffee mug that says “Have you tried turning it off and on again?”. Then the boss comes back from a conference with a MacBook Air. This series follows sysadmin Ruud as Macs arrive in his Windows network for the first time.
Every episode starts with a recognisable moment and ends with what you actually need as an admin: what’s going on, how to fix it with Intune, Entra ID and Apple Business, and Ruud’s lesson. Tongue in cheek, but always technically accurate.
The cast
- Ruud, sysadmin, 52, started out on Windows NT4. Calm, dry, a little stubborn and secretly curious.
- Marieke, managing director. Came back from a conference with a MacBook Air and “a good feeling about it”.
- Sam, junior, 24, grew up with an iPhone and often says “can I just?”.
- Karin, office manager and best friend of the big printer in the hallway.
Bolderman Installatietechniek is a made-up company. Any resemblance to a real business is coincidental.
Season 1
Episode 1the boss has a MacBook
Marieke comes back from a conference with a MacBook Air and wants it on the network today. Ruud first hunts for the right mouse button, then finds the real problem: the Mac was set up as a personal device and needs to be enrolled properly.
Episode 2where’s the C drive?
Ruud goes looking for the C drive on Marieke’s MacBook and doesn’t find a single letter. This is how APFS, the home folder, hidden folders, storage and network shares work on a Mac, mapped to what you already know from Windows.
Episode 3looking for Group Policy
Ruud types gpedit.msc into Spotlight and gets Pages. This is how Mac management works: configuration profiles, DDM and scripts through Intune, plus what you can’t enforce on a BYOD Mac.
Episode 4two passwords, one user
Marieke changes her Microsoft 365 password and her Mac keeps wanting the old one, while the keychain won’t stop asking. Ruud learns that a Mac has two identities and that Platform SSO with Entra ID brings them back together.
Episode 5I clicked Don’t Allow
Ruud tries to help Karin with her new Mac remotely, but all he sees is a mountain lake and none of his clicks land. Why Don’t Allow on a Mac is just security working, and how to set up screen recording, accessibility and remote support properly.
Episode 6the Mac that never shuts down
Marieke’s MacBook hasn’t restarted in 47 days, and Ruud points at his mug. But sleep is fine on a Mac. The real problem is the update that has been waiting two weeks for a restart.
Episode 7where’s the image?
Marieke orders five more Macs and Ruud reaches for his notepad to plan a golden image. Why imaging doesn’t work on Apple silicon anymore, and how Apple Business and Intune set up your Macs without you opening the box.
Episode 8shouldn’t it have antivirus?
The cyber insurer wants to know if every endpoint has antivirus, and Sam is sure Macs don’t get viruses. What macOS already protects, why infostealers are still a real risk, and how to put Defender on the Mac with Intune.
Episode 9the personal Apple Account
Ruud finds the company’s quotes in Marieke’s personal iCloud, right next to her holiday photos and her kids’ messages. Here’s how to keep business data and personal stuff apart on the Mac.
Episode 10the FileVault key nobody has
Henk from sales comes back from Crete with a tan and no memory of his Mac password. Ruud searches Entra for a BitLocker key out of habit, but a FileVault key that was never stored in Intune is a key nobody has.
Episode 11the department printer
Karin prints from her new Mac to the big multifunction printer in the hallway, and nothing comes out. Ruud finds out that print server PRINT01, badge-release secure print and a driver from 2014 make quite a puzzle.
Episode 12there is no Patch Tuesday
In September Marieke clicks Upgrade and suddenly she’s on Golden Gate, before anyone tested the VPN or the accounting app. Ruud misses his Patch Tuesday, then finds out the Mac has a rhythm of its own.
Sound familiar?
Running into Macs in your own Windows environment, or got a story that belongs in season 2? Email frank@analystict.nl. Analyst ICT helps organisations run Macs alongside Microsoft 365, Entra ID and Intune.