Primordial black holes (PBHs), if they exist, may shed light on long-standing questions on the nature of dark matter and mechanism driving cosmic inflation. If we associate their origin to the presence of enhanced primordial scalar fluctuations generated during inflation, the underlying dynamics that populates these objects can also provide distinctive sources of gravitational waves (GWs), potentially detectable with current or forthcoming GW experiments. Therefore, their population, along with the associated GW signal offer promising opportunities to shed light on the nature of inflation, by opening up a unique window to its dynamics at scales inaccessible by conventional CMB probes. In this talk, I will review some of the compelling inflationary scenarios able to trigger the formation of such objects in the post-inflationary universe by enhancing the amplitude of the primordial scalar perturbations. In this context, I will discuss single and multi-field realizations with a focus on theoretical aspects of model building discussing common themes shared among models in conjunction with their distinctive phenomenological implications in the form of a primordial GW background.