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

[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.
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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

boxstarter/Boxstarter.Chocolatey/Install-BoxstarterPackage.ps1

Line 814 in cd6f1f5

function Wait-ForSessionToClose($session) {

) 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

-

Additional Context

No response

[mwallner]

Def. need to look at https://learn.microsoft.com/de-de/powershell/module/microsoft.powershell.core/about/about_remote_disconnected_sessions?view=powershell-5.1
=> check if SessionState / "opened" will be updated on every possible disconnect

[mwallner]

might relate to #487