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Install-BoxstarterPackage gives incorrect result when host-reboot is pending and Wait-ForSessionToClose times out #583

@mwallner

Description

@mwallner

Checklist

  • I confirm there are no unresolved issues reported on the Chocolatey Status page.
  • I have verified this is the correct repository for opening this issue.
  • I have verified no other issues exist related to my problem.
  • I have verified this is not an issue for a specific package.
  • I have verified this issue is not security related.
  • I confirm I am using official, and not unofficial, or modified, Chocolatey products.

What You Are Seeing?

When installing a package remotely via Boxstarter and a reboot is triggered,- it will not wait for the reboot if the target host doesn't reboot within 2 minutes.
After the timeout of 120 seconds (see https://github.com/chocolatey/boxstarter/blob/cd6f1f57743acb49c9b1165a434bae4e49fdfd4e/Boxstarter.Chocolatey/Install-BoxstarterPackage.ps1#L814) it will silently assume that the host has disconnect and try to reconnect.
The reconnect will succeed to a host that is still waiting for the reboot to happen. (i.e. when the reboot is being delayed by a locked file, windows update, volume defrag etc.)
Boxstarter will start the installation which will most likely fail due to the host rebooting at some point.

What is Expected?

When hitting a timeout during installation, the process should not continue without error/corresponding logging.
=> the timeout for reconnecting to a host should be a configurable setting (when dealing with certain environments where we cannot guarantee a reboot will be carried out in timely manner)

How Did You Get This To Happen?

Install any Boxstarter package on a target host that has a CBS reboot pending and won't restart within 2 minutes. (i.e. because a volume-defrag is running)

System Details

  • Operating System: Windows
  • Windows PowerShell version: 5
  • Chocolatey CLI Version: 2.2.2
  • Chocolatey Licensed Extension version: -
  • Chocolatey License type: -
  • Terminal/Emulator: remote / PowerShell ion conhost

Installed Packages

-

Output Log

-

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2 - WorkingA user or team member has started working on the issue.BugIssues where something has happened which was not expected or intended.

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