The error you are getting might be related to KB79306
Can you try the Solution mentioned in that KB?

And it just sits there and in the vCenter, the VM is waiting for a response to the dreaded “Disconnect anyway and override the lock?” question.

I then get the timeout error:
Set-CDDrive : 5/04/2023 8:26:46 PM Set-CDDrive The operation for the entity “MyVMWithACDROM” failed with the following message: “Connection control operation failed for disk ‘ide1:0’.”. Connection control operation failed for disk
‘ide1:0’.
At C:\Users\jmilano\Documents\PowerShell_Scripts\AnswerCDROMQuestion.ps1:52 char:1
+ Set-CDDrive -CD $cd -NoMedia -Confirm:$false -ErrorAction Stop
+ ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~
+ CategoryInfo : NotSpecified: (:) [Set-CDDrive], GenericVmConfigFault
+ FullyQualifiedErrorId : Client20_TaskServiceImpl_CheckServerSideTaskUpdates_OperationFailed,VMware.VimAutomation.ViCore.Cmdlets.Commands.VirtualDevice.SetCDDrive

I also noticed your sample code used to run the script shows the command:
Set-CDDriveAndAnswer -VM LinuxBox

However the name of the VM to disconnect the CDROM is actually passed to the Name parameter so the command should be:
Set-CDDriveAndAnswer -Name LinuxBox

But I guess this is a result of lots of testing and code changes along the way. Something small.

If you remove the line
“Connect-VIServer -Server $vServer.Name -Session $vServer.SessionSecret | Out-Null”
the script will run, but the vSphere question will not be captured/answered.

For info:
The try/catch variant from these threads does not work for me, as no exception is thrown.

Is there a solution that can be used via the task scheduler?

In fact, my solution does something similar, it runs code in the background that polls for the question, and then tries to answer it.
Sometimes that background task might fail I noticed.

The reason I ask this is that when I run the command:
Set-CDDrive -CD $cd -NoMedia -Confirm:$false

The VM Summary screen shows the question and is waiting for an answer.

I then opened another PowerShell command dialog, connected to the same vCenter as the VM in question, and ran the following:

PS C:\Users\MyUsername> get-vmquestion

Text Options Default
—- ——- ——-
The guest operating system has locked the CD-ROM {button.yes, button.no
door and is probably using the CD-ROM, which can button.no}
prevent the guest from recognizing media changes.
If possible, eject the CD-ROM from inside the
guest before disconnecting. Disconnect anyway and
override the lock?

PS C:\Users\MyUsername>

I then ran this command and the CDROM unlocked:
Set-VMQuestion -VMQuestion $question -Option “button.yes” -Confirm:$false

So I guess if I could load a new process which delays by 10 seconds, then queries the question on the VM and then answers it with “button.yes” and shuts down, this would work, but I’m not sure how to code this.

The VM I am testing with has the following properties set:
Connected To: Host Image File
File: [] MyImageFile.iso