Maintenance windows: smarter scheduling

[allenhouchins]

• @noahtalerman: User requested this because having all calendaring events occur on the same day can cause an increase in IT support tickets and risk downtime for a large number of employees at the same time.
  • @noahtalerman: Eventually, Fleet could schedule the events at varying times and varying days for each end user.
• @noahtalerman: User requested this because Fleet schedules a new calendar event on the next Tuesday if the end user is still failing. They want the new calendar event to happen sooner.
• @mikermcneil: Nice to have: it would help if the calendar event told you whether or not this was automatic maintenance taking over your computer, or something that you have to do yourself. But either way, the calendar got me to do it.
  • The risk is that people get used to never opening the calendar event, because they assume it's something IT is doing for them
  • One way to potentially help here is to configure (if configurable- otherwise, maybe try tweaking in code) the reschedule interval. Eg. if I didn't do it at 17:00, then at 17:30, if it rescheduled immediately (more or less) to be later that same day or early the next morning, it would have a stronger psychological effect (as an employee, you feel like you can't get away with ignoring it)

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[noahtalerman]

Problem

Currently, the calendaring automation will schedule and reschedule its event if the issue is still not resolved on the following Tuesday. This means a device might remain in an undesirable state for an extended period of time.

https://fleetdm.slack.com/archives/C084F4MKYSJ/p1741274272877179

This also means that everyone is performing actions on the same day which could lead to an increase in IT support tickets and risking other down times. In some cases this could be hundreds or thousands of employees.

What have you tried?

N/A

Potential solutions

The automation should schedule calendaring events at the next available time slot starting at 24 hours after the policy has been evaluated for the device.

What is the expected workflow as a result of your proposal?

Calendaring automation events will be more distributed and users will get compliant or back in a desired state more quickly.