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You'd probably need to use the SDK for that, not Pulumi, I think...

Being able to SSH to the instance to do stuff. I think you are right in that using AWS Systems Manager might be a better idea. I hadn't used it until last night so not too sure what it can do. What I am trying to do is use an ED25519 SSH key with my instance but the AWS API only supports RSA which is really annoying.

I think I'd rely on the SDK for waiting until SSH is ready. Possibly in conjunction with automation-api, if you wanted Pulumi to do more stuff after SSH is available. SSM is more powerful than I realized until today (I've only been using command documents, the automation documents are looking good right now), so if whatever you want SSH for can be done via sh / powershell, then SSM might be a better way to go.

@worried-queen-62794 which SDK/language are you using?

Python

try this: https://github.com/pulumi/examples/tree/master/aws-py-ec2-provisioners

Yep that's what I started off using.