How can we get users to free up disk space so their laptops can install updates?

Automate as much cleanup as possible. Storage Sense, OneDrive Files On-Demand, browser and application cache cleanup, and monitoring for devices below a minimum free-space threshold can help. Set a target such as keeping 10–20% of the drive free, then automatically alert or create a ticket when a laptop falls below it.

Some laptops simply don’t have enough capacity anymore, especially 256 GB systems with large applications, caches, and major updates that temporarily need a lot of free space. After a reasonable amount of troubleshooting, replacing the device or reimaging it may be cheaper than repeatedly spending technician time on it.

If you use device management, create compliance rules based on the Windows build or update status. After a reasonable deadline, restrict access to company resources until the device is current. That gives users a clear incentive without requiring IT to repeatedly chase them.

Make the deadline and consequences clear: update notices, reminders, and then restricted access for devices that remain noncompliant. For users whose required software genuinely needs the storage, document the exception and plan a larger drive or replacement instead of expecting endless manual cleanup.

Treat this as an organizational policy issue, not just a technical support task. Get management and HR to approve a grace period and define what happens when someone remains out of date or refuses to free up space. Users are much more likely to act when the requirement is formal and backed by management.