There are more than one million described species of insects. Understanding the processes and mechanisms that gave rise to this immense diversity has been a long-standing goal of evolutionary biology. With the advances in molecular technologies and phylogenetic modeling, we can begin to connect macroevolutionary patterns and microevolutionary processes to better understand the evolutionary history of insects. The goal of this dissertation is to use a multi-level approach to understand the evolutionary dynamics of the insect family Diaspididae (Hemiptera: Coccomorpha). I start at the macroevolutionary level in Chapter 1. I use a published molecular dataset to estimate diversification rates of the family Diaspididae and understand within family diversification dynamics. These analyses reveal that the diversification of the group is governed by at least three different rate regimens and is characterized by an early burst in speciation rates. In the next two chapters, I focus on a North American species that has been a challenge for armored scale systematists, Diaspidiotus ancylus. In Chapter 2, I drop down to a shallower phylogenetic scale and look at the Diaspdiotus ancylus species complex. I developed a novel molecular dataset of ultraconserved elements (UCEs) to estimate species boundaries of D. ancylus and its close relatives. I find evidence for three distinct evolutionary lineages within D. ancylus that are morphologically indistinguishable. In Chapter 3 I move further down into a microevolutionary level scale and test the utility of the chosen UCEs to look at the population structure of one of the D. ancylus lineages. I find evidence for population differentiation primarily along host plant. Together these chapters paint a picture of a group divided into metapopulations, whose molecular evolution and reproductive isolation outpaces morphological evolution, and whose evolutionary history is marked by explosion into their ecological niche.