Plugin license key is lost every time I update Craft CMS
@Dalton I would say that's indeed the issue (using the project.yaml file), at least at first glance. 

Every time you're pushing the project.yaml file to your server, it'll overwrite your server's project.yaml file. Because the plugin isn't licensed locally, you're basically removing the license each deploy. 

Can you register the license locally, then push your project.yaml file? You'll notice locally, as soon as you enter a license key, the file will change to store this license key. Things should stay in sync from then on.