Software-intensive systems present several challenges to the contracting officer (CO) and contracting officer representative (COR). These include what questions to ask at each stage of the contracting process (i.e., Initial Concept Study and contract execution) and how to interpret and evaluate the contractors’ answers. Currently, guidance is scattered among numerous references, directives, and instructions; the COR has to sift through this documentation to find the relevant information. The COR Desk Guide Wiki solves this problem through the creation of a single point of reference, consisting of a curated set of Department of Defense and local documents, templates, and checklists to aid the COR in addition to the general benefits of information sharing and collaboration provided by a Wiki. Built on SharePoint 2013, the initial prototype—though incomplete—demonstrates the potential of this approach. The Wiki can be accessed remotely, through the Carnegie Mellon Software Engineering Institute’s External Collaboration Environment, or it can be imported into an existing SharePoint 2013 instance and be up and running in less than a day.