Tanglegrams are formed by taking two rooted binary trees T and S with the same number of leaves and uniquely matching each leaf in T with a leaf in S. They are usually represented using layouts, which embed the trees and the matching of the leaves into the plane as in Figure 1. Given the numerous ways to construct a layout, one problem of interest is the Tanglegram Layout Problem, which is to efficiently find a layout that minimizes the number of crossings. This parallels a similar problem involving drawings of graphs, where a common approach is to insert edges into a planar subgraph. In this paper, we will explore inserting edges into a planar tanglegram. Previous results on planar tanglegrams include a Kuratowski Theorem, enumeration, and an algorithm for drawing a planar layout [5,16,15]. We start by building on these results and characterizing all planar layouts of a planar tanglegram. We then apply this characterization to construct a quadratic-time algorithm that inserts a single edge optimally. Finally, we generalize some results to multiple edge insertion.