Although IPv6 has been the next generation Internet protocol for nearly 15 years, new evidences indicate that transitioning from IPv4 to IPv6 is about to become a more pressing issue. This paper attempts to quantify if and how such a transition may unfold. The focus is on connectivity quality,'' e.g., as measured by users' experience when accessing content, as a possible incentive (or disincentive) for migrating to IPv6, and on translation costs'' (between IPv6 and IPv4) that Internet Service Providers will incur during this transition. The paper develops a simple model that captures some of the underlying interactions, and highlights the ambiguous role of translation gateways that can either help or discourage IPv6 adoption. The paper is an initial foray in the complex and often puzzling issue of migrating the current Internet to a new version with which it is incompatible.