Let $T$ be a given (finite) tree.
Question 1: Is it always possible to add edges to $T$ to obtain a $2$-connected outerplanar supergraph $G$?
Question 2: If the answer to Question #1 is negative, can the trees for which it is possible be characterized?
Question 3( Defect form of Question 1): Let $T$ be a rooted tree with root vertex $v_{0} \in V(T)$. Is it always possible to add edges to $T$ to obtain a $2$-connected planar graph $G$ with a plane embedding in which $v_{0}$ is the only internal vertex?