HTTP adaptive streaming (HAS) has become the de facto mode of delivering content for over-the-top (OTT) video services , both live and on-demand. As these services grow and mature, so does the need for viable, robust capabilities for monetization and personalization. These capabilities (and more) are driving many programmers and broadcasters to look to DAI to help drive additional revenue streams on the plethora of devices now capable of streaming. This paper and presentation will explore some of the key considerations related to OTT DAI. First, what are the the fundamentals of ad stitching and the differences between legacy client-side ad insertion (CSAI) and today's server-side ad insertion (SSAI)? How can those who deploy OTT services defeat the very real concern posed by ad blockers and reach the audiences that seek their content? This paper will also look at IAB standards (e.g., VAST/VPAID) and how OTT adverts can now deliver national/local/regional payloads within ad pods, essentially mimicking the broadcast world and making true monetization a reality for content creators who have long looked at OTT and broadcast as separate worlds. Finally, we will discuss the implications of personalization and true user targeting, which are now a reality for OTT services using a variety of data sources (GPS, postal code, IP tables). These capabilities represent a great advance for OTT and the granular experiences it can provide. This means that service providers can deliver adverts that are more relevant to the viewer, OTT is more impactful as an overall experience, and will likely drive ad rates (and revenue) higher over time. This will also include interactive overlays, where advertisers can now provide viewers on connected devices with tangible elements (coupons) they can redeem. These new capabilities help to cement relevant experiences for the viewer and audience and increase revenue opportunities for OTT providers.