No matter how you like to participate in developer communities, Pulumi wants to meet you there. If you want to meet other Pulumi users to share use-cases and best practices, contribute code or documentation, see us at an event, or just tell a story about something cool you did with Pulumi, you are part of our community.

Pulumi Community

I figured it out. The problem is that the userdata parameter wasn't a direct Output object, so it wasn't being tracked as a dependency, meaning that it got skipped when rendering the values.

I had to put the entire rendering of the string into an Output.apply function call.