Provisioning Script using CustomScriptExtension on Windows2019 Fails - azure

Question

I'm trying to wrap my brain around an issue with either the TF Code, or me. I've got a VM Set that I'm mapping over, and on each one, I have a CustomScriptExtension that should install Docker on the VMs.
When I run the plan, it builds the VMs, and the Custom Script runs, however when I RDP into the machine, and attempt a docker info It's telling me that docker isn't installed.
A quick cursory glance of C:\Packages\Plugins\Microsoft.Compute.CustomScriptExtension\1.*\Downloads\ Shows that the installer script is indeed being downloaded, but it doesn't seem to be installing.
Here's the AzureRM Resource (Sanitized):
resource "azurerm_virtual_machine_extension" "bootstrap-scripts" {
for_each = local.XXXXXX
name = "${each.key}-bootstrap"
virtual_machine_id = module.XXXXXXXX[each.key].virtual_machine_id
publisher = "Microsoft.Compute"
type = "CustomScriptExtension"
type_handler_version = "1.10"
settings = <<SETTINGS
{
"commandToExecute" : "powershell -ExecutionPolicy Unrestricted -File install-docker-ce.ps1",
"fileUris" : ["https://raw.githubusercontent.com/microsoft/Windows-Containers/Main/helpful_tools/Install-DockerCE/install-docker-ce.ps1"]
}
SETTINGS
}
And the output from the log at C:\WindowsAzure\Logs\Plugins\Microsoft.Compute.CustomScriptExtension
[
{
"version":"1",
"timestampUTC":"2022-10-21T20:03:44.6989395Z",
"status":{"name":"powershell -ExecutionPolicy Unrestricted -File install-docker-ce.ps1",
"operation":"Command Execution Finished",
"status":"success",
"code":0,
"formattedMessage":{
"lang":"en-US",
"message":"Command execution finished"
},
"substatus":[
{
"name":"StdOut",
"status":"success",
"code":0,"formattedMessage":{
"lang":"en-US",
"message":"Querying status of Windows feature: Containers...\r\nEnabling feature Containers...\r\nWARNING: You must restart this server to finish the installation process.\r\nRestart is required; restarting now...\r\nCreating scheduled task action (C:\\Packages\\Plugins\\Microsoft.Compute.CustomScriptExtension\\1.10.12\\Downloads\\0\\install-docker-ce.ps1 )...\r\nCreating scheduled task trigger...\r\nRegistering script to re-run at next user logon...\r\n"
}
},
{
"name":"StdErr",
"status":"success",
"code":0,
"formattedMessage":{
"lang":"en-US",
"message":"Register-ScheduledTask : No mapping between account names and security IDs was done.\r\n(12,8):UserId:\r\nAt C:\\Packages\\Plugins\\Microsoft.Compute.CustomScriptExtension\\1.10.12\\Downloads\\0\\install-docker-ce.ps1:150 char:5\r\n+ Register-ScheduledTask -TaskName $global:BootstrapTask -Action $a ...\r\n+ ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~\r\n + CategoryInfo : NotSpecified: (PS_ScheduledTask:Root/Microsoft/...S_ScheduledTask) [Register-ScheduledTa \r\n sk], CimException\r\n + FullyQualifiedErrorId : HRESULT 0x80070534,Register-ScheduledTask\r\n \r\n"
}
}
]
}
}
]
from what I'm reading, it seems to set up the scheduled task to reboot the server, but it looks like it never does? However even after a manual restart, it's still not installed.
Can anyone shed some light on this?
EDIT: I forgot to mention that I cannot use anything out of the Azure Public Marketplace, in case someone wanted to mention using a premade image. I am relegated to using images that are stored in our private collection