The networking community continues to create new technologies and update existing ones to improve the quality, reliability, and “tailorability” of data networks. However, whenever Internet service providers attempt to productize “tailorability” and sell it explicitly to end customers as a premium service over best effort connectivity, they either fail to overcome net neutrality concerns or struggle to gain market traction. For this article, we focus only on those networking protocols, technologies, or standards whose goal is to offer tailored connectivity to paying customers on a public network and refer to them as differentiated QoS (D-QoS) standards. This article makes two contributions to the understanding of the goals of D-QoS standards. First, it explores their techno-economic market trajectory to understand the factors that determine success. In doing this, we acknowledge that while there is wide variation and dissimilarity in their underlying technical properties, the expectation and goal for all D-QoS standards is that they will be used to provide guaranteed connection for which customers could be prepared to pay. As such, we consider Layer 2/3 technologies (e.g., ATM, frame relay, MPLS), signaling technologies (e.g., RSVP), data packet markers (e.g., IP ToS, DiffServ, WME, QCI), and end-to-end separation solutions (e.g., leased lines, network slicing) as a single cohort and analyze them together. Second, by exploring the parallels with 5G network slicing, we argue that despite its inherent technical differences with other D-QoS standards, the commercial performance of network slicing may end up resembling that of previous D-QoS standards. Consequently, we seek to learn lessons from previous D-QoS attempts and suggest that enterprise-focused 5G slices, running within a single service provider’s domain and with binding service level agreements, will have the highest chance of success in the short/medium term.