I created a simple playbook to test this out and I baked an AMI which curls 
the callback endpoint on startup (added as user data).

If my inventory needs to contain the instance that triggers the callback, 
how does that happen if, by definition, the machine that's just coming 
online is not in my inventory? Does the request to the callback endpoint 
trigger an inventory sync?

Also, after debugging this for a bit, I'm seeing that the response from the 
callback endpoint is {"msg":"No matching host could be found"}. 

Any ideas?

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