Non-terminating (dependencies of) definitions can lead to logical contradictions, for example when defining a boolean constant as its own negation. Some proof assistants thus detect and disallow non-terminating definitions. Termination is generally undecidable when constants may have different definitions at different type instances, which is called (ad-hoc) overloading. The Isabelle/HOL proof assistant supports overloading of constant definitions, but relies on an unclear foundation for this critical termination check. With this paper we aim to close this gap: we present a mechanised proof that, for restricted overloading, non-terminating definitions are of a detectable cyclic shape, and we describe a mechanised algorithm with its correctness proof. In addition we demonstrate this cyclicity checker on parts of the Isabelle/HOL main library. Furthermore, we introduce the first-ever formally verified kernel of a proof assistant for higher-order logic with overloaded definitions. All our results are formalised in the HOL4 theorem prover.