Said It Here

Free ways to push updates and force reboots

Pushing updates for free often fails because machines will not restart automatically to finish the installation. End users never restart their computers on their own, and servers frequently get stuck in a pending reboot state during scheduled maintenance windows. This forces administrators to manually trigger the reboots via RDP or remote tools just to get the updates installed.

What people tried

Every workaround mentioned in the threads below. We haven’t tested any of them — and nobody here is claiming they worked.

  1. 1
    Using free tiers of cloud endpoint patch management tools like Action1
  2. 2
    Setting local GPO or Intune update deadline policies to force reboots after a grace period
  3. 3
    Scripting updates with PowerShell using winget or Chocolatey and logging to a network share
  4. 4
    Bundling patch management through endpoint security software like ESET or Malwarebytes
  5. 5
    Baking a pre-patch reboot into the maintenance script to ensure a clean state.
  6. 6
    Running automated scripts to query the pending reboot flag and force a restart without interaction.
  7. 7
    Relying on application-level High Availability (HA) to manually reboot servers whenever needed.
  8. 8
    Configuring dual-reboot maintenance windows (one reboot before patching, one after).
  9. 9
    Executing scheduled weekly reboots regardless of patch cycles to clear any lingering states.

In their words

Unedited, grouped by where they were said, most upvoted first within each place, each linked to the thread it came from.

r/sysadmin2 people · October 2026

“what's the best way to push updates?”source ↗

“Obviously this is a thing where users never restart their computers to complete the updates and such.”source ↗

“What's free way to do it?”source ↗

Lazengann86 · r/sysadmin · 24 upvotes

“for one reason or another some servers remain in a pending reboot state after scheduled maintenance window monthly CUs install.”source ↗

voyager_toolbox · r/sysadmin · 8 upvotes

“we have those: dev, test, prod. but a lot of times servers just don't reboot after install”source ↗

voyager_toolbox · r/sysadmin · 1 upvotes

“we have 4 hour maintenance windows. sometimes they do not install and have to be triggered, sometimes just stuck on reboot or sometimes .NET installs first asks for a reboot while CU stays there needing a trigger via Remote Click Tools or RDP”source ↗

voyager_toolbox · r/sysadmin · 1 upvotes

Where this came up

People with this problem also raised