Auto Bootstrap Windows Node

I’m trying to create an auto bootstrap script that will install the chef client msi, dynaically create the client.rb file and add the necessary paths. When I run chef-client at the end of my script I get the following error.

INFO: Client key C:\chef\client.pem is not present - registering
FATAL: OpenSSL::X509::CertificateError: nested asn1 error

The bootstrap works when I do it via WinRM.


are you trying to do a self bootstrap? is the script running on the node? does the node has your organisations validator on it to bootstrap?

The knife bootstrap windows (I assume this is what you are referring to when bootstrapping over winrm) uses the client key on the local workstation or a validator key and uploads it to the node.

For these kinds of auto bootstrapping scenatrios, you need to have a validator key on the node in order for it to obtain a client.pem. The link to the unattended install docs below should walk you through that.


I wrote a cookbook that we use in our environment. Maybe it helps you out.

If I have to create a data bag for all the nodes, that would be pretty painful. Unless I’m missing something here?

You have to create just the bootstrap DataBag and n DataBag Items for each Node you want to bootstrap.
When you use the Item syntax from the readme file you’ll see it’s pretty easy.