So.. macOS Sierra was publicly released by Apple, and at Just Eat we’re all about embracing change so having the new update ready shortly after it’s release was key in a future thinking deployment. For anyone that attended the JAMF Nation London Roadshow you would have known my aim was to be day 1 ready for macOS Deployment to a certain degree but in hindsight waiting for a public releases for certain products to be macOS Sierra compatible pushed my day 1 timeline to a week 1 timeline, nevertheless here’s how I moved forward with my “Week 1” macOS Sierra Deployment.

 

Finding Eligible Machines

So simply I had to find all the machines in my environment which were eligible for the macOS Sierra upgrade, simple enough I found out the requirements for macOS Sierra, a minimum of about 86% hard drive capacity, along with all machines that were Mac OS X 10.7.5 or higher, and a minimum of 2GB RAM. So heading into our JSS I created a “macOS Sierra Upgrade Eligible” Smart Group :

Finding Machines that already have macOS Sierra

So on the flip side we had a few machines that already had macOS Sierra, so the next quest was to find these simple so we don’t target these machines with the macOS Sierra upgrade policy, again I created a smart group and looked for machines that “Have macOS Sierra Installed“, simple find operating system like 10.12:

 

macOS Sierra Public Release into Casper Admin

So if you haven’t done so already upgrade your JSS to the latest 9.96 to make use of the latest Casper Admin.

Next, head over to the Mac App Store (preferably on a clean Mac) and download the latest macOS Sierra Release:

Once downloaded quit the “Welcome to macOS Sierra Installer” when it opens, and head over to your Applications folder, open Casper Admin and drag the Install macOS Sierra application into Casper Admin, let it upload to your distribution point. Once uploaded, JAMF Software automatically assigns the package a priority of 1, head over to the General tab categorise the package to something relevant i.e. Operating System.

Optional, replicate this to all your distribution points if you want your Mac’s to utilise the upgrade from there.

macOS Sierra Upgrade Self Service Policy

Now that your package has been uploaded to Self Service you can go ahead and make your Self Service policy to perform the upgrade.

Create a New Policy with the following:

Options Tab

General

Display Name: macOS Sierra 10.12

Category: Operating System

Trigger: (Blank)

Available Offline: Checked (Optional)

Target Drive: /

Packages

Add the “Install macOS Sierra.InstallESD.dmg” package which you uploaded to Casper Admin earlier.

Restart Options

Startup Disk: OS X Installer

No User Logged In Action: Restart Immediately

User Logged In Action: Restart

Perform authenticated restart on computers with FileVault 2 enabled: Checked (Only check if you have FileVault configured on your Mac’s)

Delay: 1 (Set to your preference)

Maintenance

Update Inventory: Checked

Scope Tab

Now we want to target the scope to all the machines eligible and exclude all the machines that have macOS Sierra already. So set your Target scope to the “macOS Sierra Upgrade Eligible” smart group you created earlier and exclude the “Has macOS Sierra Installed” smart group.

Self Service Tab

Now we can make the policy available in Self Service, check the checkbox and give the button a relevant name i.e. “Upgrade” . Give it a nice description, give it a nice icon and give it a category it should display in.

User Interaction Tab

Lastly you can add a custom notification to your end users, so for example I bring up a notification that tells users their upgrade process is about to begin, and a customised restart message which relates back to the “User is Logged in Action” and 1 minute restart I have configured. So this section is entirely up to you but here’s an example of what I did:

That’s it, Save your policy and you’re ready to go!!!

 

TEST, TEST, TEST!

It’s important to test the upgrade method to ensure the upgrade works as expected from here you’ll understand any potential issues you’ll be faced, so you may want to hold off adding in your Target scope until your testing phase is complete. If you’ve successfully tested then carry on!

 

Final Result

So if the Mac’s in your environment meet the system requirements they’ll automatically be entered into the “macOS Sierra Upgrade Eligible” smart group, which will then show your policy on Self Service. Week 1 macOS Sierra. Done!