

I recreated a similar environment using the Python 3.11 on a Windows with Rundeck 4.8.0 box, I obtained the Python 3 wizard from here.
To test:
Install the Python 3.10/3.11 on the same Rundeck Windows box, just make sure that the user that launch rundeck can reach and execute the “python” program (you can test it opening a new PowerShell terminal and type the “python” command, you will see a typical python prompt). Also, make sure to mark the “Add to PATH” checkbox in the installation process.
Install the plugin dependeces: In a administator PowerShell terminal just execute: pip install pywinrm urllib3 requests.
Configure the windows box to receive WinRM connections following this.
Delete the localhost model source and then, Add the following XML file model source, check the content:
<?xml version="1.0" encoding="UTF-8"?>
<project>
<node name="Hostname"
description="Windows Server"
tags="windows"
hostname="localhost"
osArch="amd64"
osFamily="windows"
osName="Windows Server 2012 R2"
osVersion="6.3"
username="myuser"
winrm-password-storage-path="keys/winpasswd"
winrm-authtype="basic"/>
</project>
Add the “myuser” windows password on the Rundeck keystorage, “keys/winpasswd” path on my example.
In the Project Settings > System Configuration > Node Executor tab, select “Python” (not “Python 3”), this is the default Python 3.10/3.11 interpreter in Windows systems.
Dispatch any command via WinRM to the new local Windows node.
Hope it helps! :-)