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Hello,

The "WindowsLicensingPlugin" does not have the option to configure it at boot time with a serial key.

You can use the custom script (OpenStack feature) feature to send in a script with the code to license the Windows vm at boot time and that will be executed by Cloudbase-init. But by doing that you will expose the serial key in the metadata which can be accessed by everyone who uses the machine.

Cloudbase-Init has the feature the feature of using the KMS and AVMA known keys, is properly set (but in this case you require a KMS server to be existent in your environment or an AVMA compliant Microsoft subscription. More info here:
https://technet.microsoft.com/en-us/library/ff793434.aspx
https://docs.microsoft.com/en-us/previous-versions/windows/it-pro/windows-server-2012-R2-and-2012/dn303421(v=ws.11)
Cloudbase-Init example configuration:

[DEFAULT]
activate_windows=True
set_kms_product_key=True
kms_host="kmshost:1688"
#or
set_avma_product_key=True

Another common workflow is to pre-activate the image on creation using a MAK (Multiple Activation Key). More info here:
https://technet.microsoft.com/en-us/library/ff793435.aspx
You can achieve this by using the image creation tool:
https://github.com/cloudbase/windows-openstack-imaging-tools

Thank you,
Adrian Vladu