Getting OS updates installed on end user devices should be easy. After all, it’s one of the simplest yet most impactful ways that every employee can practice good security. 

On top of that, every MDM solution promises that it will automate the process and install updates with no user interaction needed.

Yet in the real world, it doesn’t play out like that. Users don’t install updates and IT admins won’t force installs via forced restart.

Let’s talk about the second problem first. Sure, you could simply schedule updates for all your users, and have them restart during non-work hours. But this inevitably leads to disruptions and lost work. This, in turn, leads to users (especially executives) who simply demand to be left out of your update policy. The bottom line is: any forced restarts without user approval will lead to data loss events, and that makes them so unpopular that they are functionally unusable.

There is another class of tools that claim to get users to install updates themselves, through “nudges.” These reminders pop up with increasing frequency until users relent or the timer runs out. This is an improvement, since it involves users in the process, but users still tend to delay updating as long as possible (which for some tools can be indefinitely).

At Kolide, OS updates are the single most common issue customers want us to solve. They come to us because we have a unique (and uniquely effective) approach to device compliance.

With Kolide, when a user’s device–be it Mac, Windows, Linux, or mobile–is out of compliance, we reach out to them with instructions on how to fix it.

The user chooses when to restart, but if they don’t fix the problem by a predetermined deadline, they’re unable to authenticate with Okta. (At present, Kolide is exclusive to Okta customers, but we plan to integrate with more SSO providers soon.)

If your fleet is littered with devices that stubbornly refuse to update, then consider these two principles:

1. You can’t have a successful patch management policy without involving users.
2. You can’t get users to install patches unless you give them both clear instructions and real consequences.

Installing OS updates is a top priority for both security and IT, and when you make it part of conditional access, you can finally get it done without massive lists of exemptions or massive piles of support tickets.

To learn more about how Kolide enforces device compliance for companies with Okta, click here to watch an on-demand demo.

Our thank to Kolide for sponsoring MacStories this week.

With Drafts, you can capture text on any Apple platform, wherever you are. There are iPhone, iPad, Mac, and Apple Watch versions of Drafts, which makes capturing notes, ideas, messages, tasks, and links fast and simple.

Moreover, Drafts incorporates a powerful actions system for automating your workflows. Integrate Drafts with hundreds of apps and services, including tools like:

• Obsidian
• Airtable
• Notion
• Things

Drafts also has deep support for Apple’s Shortcuts app, with over two dozen actions for manipulating text, managing Drafts, and integrating your captured text with other OS-level features. This combination makes Drafts one of the most sophisticated ways to create text automations on Apple’s platforms.

To help you get started, Drafts offers extensive documentation and guides for integrating with a wide variety of other tools. Plus, there’s a directory of user-created and curated actions and a vibrant community of users who are always around to help each other.

It’s easy to see why Drafts won last year’s MacStories Selects Lifetime Achievement award. The app is flexible, customizable, and has been regularly updated since the early days of the App Store to support the latest technologies of Apple’s OSes. That’s why if you’re looking to capture text and love to automate your workflows, Drafts is the app you need.

Right now, MacStories readers who are new to Drafts Pro or resubscribing can get a 3-month trial for free. This deal is available until December 14, 2023. For all the details and suggestions on where to get started with the app, visit the Drafts forums here.

So, download Drafts Pro today and start tinkering over the winter holidays. It’s a great way to jumpstart your workflows for the New Year.

Our thanks to Drafts for sponsoring MacStories this week.