The paper sketches some initial results from an ongoing project to develop an ontology-based digital form for representing uncertain information. We frame this work as a journey from lower to higher levels of digital maturity across a technology divide. The paper first sets a baseline by describing the basic challenges any project dealing with digital uncertainty faces. It then describes how the project is facing them. It shows firstly how an extensional ontology (such as the BORO Foundational Ontology or the Information Exchange Standard) can be extended with a Lewisian counterpart approach to formalizing uncertainty that is adapted to computing. And then it shows how this is expressive enough to handle the challenges.