Technologies for automatic discovery and connection to a representational state transfer (REST) interface include a provider computing device communicatively coupled to a REST interface of a Web service hosted by a 3rd party. The provider computing device is configured to analyze a data representation received from a REST interface of a Web service in response to having transmitted an HTTP request to an endpoint of the Web service and determine a pattern of the data representation as a function of the analysis of the data representation. Additionally, the provider computing device is configured to generate one or more possible schemas for the REST interface based on the determined pattern. Additional embodiments are described herein.