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would it be an option to toss them in an ASG and set up a health check that isn't healthy until userdata runs?

Not really, since we have the same issue with multiple cloud providers :open_mouth:

Just a quick heads-up for everyone having the same issue (waiting for cloud-init)

Use the new remote commands (<https://www.pulumi.com/blog/executing-remote-commands/>)
```cloud-init status --wait```

Big thank you to all at Pulumi, for having remote commands :heart: