The promise of Industry 4.0 has almost every business sector and vertical striving to achieve OT/IT integration in as compressed a timeframe as possible. One of the largest – if not the largest – obstacles to achieving this requisite integration is Cyber Security. This condition adds interesting nuance to business risk decisions. These risk discussions will have multiple facets, including the obvious cyber risk profile – but also the strategic business risks. The risk of doing too much, too fast, vs. the risk of waiting too long to capitalize; how to achieve that proper balance? The result is many organizations find themselves in a “catch 22” scenario where business leader’s directives are unable to be achieved due to the inherent insecure nature of both legacy OT and ICS environments, as well as the lack of security capabilities in many new technologies and devices. This discussion will provide clarity to some of the root cause issues that are manifesting these cyber security obstacles. Potential options to achieve short-term, mid-term and long-term success by addressing these cyber challenges head-on will also be discussed – and how users, partners, stakeholders and vendors need to collaborate and adjust to realize the benefits of digitally integrated enterprises.