There was an early attempt to add OCSP support to puppet in https://github.com/puppetlabs/puppet/pull/510. However, it relied on the indirector as the mechanism for making OCSP requests and it added OCSP support for both agents and servers (so the server could act as an OCSP responder). We've since decoupled the indirector from the http client, and dropped webrick & passenger support, so that PR would need to be reworked. Also it doesn't solve the OCSP stapling issue, as changes are needed in ruby's openssl bindings to support that (https://github.com/ruby/openssl/issues/295), and those settings will need to be exposed in Net::HTTP.