MacADUK 2019: Highlights & What I’m Taking Forward

St. Paul’s and the Thames

This year’s MacADUK Conference is in the books, and I’ve made it back to the States in one piece. It was a busy week, full of socializing and engaging with colleagues, as well as learning about new topics in client management and deployment workflows, encryption details, and security philosophy. My sincerest thanks to Ben Toms and James Ridsdale from Datajar who chaired this year’s conference, and to the team at Amsys that handled logistics and details.

Highlights

Park nearby Prospero House

This year’s conference had some great sessions. When the videos are out, I would strongly recommend seeing the following sessions on the small screen:

Armin Briegel, Deployment: Modern deployment workflows for business

Deployment is a source of opportunity for every IT out there. It’s literally your coworkers’ first impression of your operation, so why aren’t you putting your best foot forward with customized deployment via Automated Enrollment and Mobile Device Management. Figuring out how to replace the older technologies of ASR-based imaging with new deployment strategies is a challenge worth embracing.

Chris Chapman, macOS in a Docker Container for Development

There’s no question that Docker and Kubernetes are key components of modern software development stacks, especially for web-oriented applications. Chris Chapman of MacStadium has taken this to a whole new level, by writing a boot loader for Kubernetes and Docker for Apple hardware, allowing you to deploy a macOS image through orchestration and docker. The more I think about this, the crazier it is, but it demonstrates a flexibility that wasn’t possible before. I’m sure this is completely unsupported, but what a phenomenal way to think about the underlying tool chains we build from. It’s called Orka, and MacStadium is looking for beta sites.

David Acland, All about digital signatures

We spend a whole lot of our admin life making sure that signatures align and are approved, but how does that process actually happen? What’s the working relationship between a hash and a signature? What’s the actual cryptographic process used to take a hash and sign it as a measure of identification integrity? David took us through the details, and it was a real pleasure. And my head didn’t explode.

Ben Goodstein, Working with APIs: Power up your scripts with real time information

APIs as part of scripts is table stakes for adminry these days, and where better to get a refresher than with a low-stakes custom API that Ben wrote for accepting data from a script. He also told us about Insomnia, a GUI app for practicing with, in order to review what’s come down from an API call, and help better gather information. It was a great session, and I learned a lot of useful things to iterate against.

Commit No Nuisance

Takeaways

I had a few big thought lines that came back a few times during the conference, and lead to some noodling in my head on walks through London. We’re once again at an inflection point in macOS Administration, much as we were in the 10.8/10.9 period, the 10.7 period, and the 10.5 period. There are changes to our management structures that are no longer flashes in a pan:

MDM is not optional.

Deployment should be automated.

Manage as little as you need to retain a presence on the platform.

Managing more than you need to results in Shadow IT and Loopholes.

IT Operations relies on trust. Not just mechanized and automated trust chains established through TLS certificates and certificate authorities, it relies on a human trust that is implicit between Management and IT, and IT and the end users, your coworkers. For any IT policy to succeed, it must come with buy-in from your coworkers, not just in your department, but in your whole organization. Systems that are deemed too complicated will be ignored. Systems that are deemed too cumbersome to be operated will spark grudges. Systems that are deemed to be unpersonalizeable will result in shadow IT usage on personal equipment.

The balance between security, usability, and management philosophy remains the single most important challenge of any IT environment, large or small. If you have a bad balance, your coworkers will fight with you, resent you, and eventually work around you and cut you out.

Having a light hand on your workstations will be fought by internal and external security guidelines, though, and you’ll need to be ready with justifications based on feedback in the event that your choices are questioned. Obviously, there are some guidelines you can’t ignore. But, the security of the platform needs to be part of your process, not bolted on, not thought of after, but holistically part of your deliberations and choices. Self-healing management is a part of that, as is centralized reporting mechanisms designed to track the state of a machine.

If IT isn’t working to enhance the culture of your organization by extending and embracing systems of participation and training, your value will be subsumed by internal groups that are doing these things. That means providing good guard rails, but also providing knowledge and power at the workstation level to enhance your colleagues’ ability to do their jobs.

IT is a human-facing department in 2019. We serve the people. We just also serve the machines they use.