In this paper, we introduce a new problem called Tree-Residue Vertex-Breaking (TRVB): given a multigraph $G$ some of whose vertices are marked "breakable," is it possible to convert $G$ into a tree via a sequence of "vertex-breaking" operations (replacing a degree-$k$ breakable vertex by $k$ degree-$1$ vertices, disconnecting the $k$ incident edges)? We characterize the computational complexity of TRVB with any combination of the following additional constraints: $G$ must be planar, $G$ must be a simple graph, the degree of every breakable vertex must belong to an allowed list $B$, and the degree of every unbreakable vertex must belong to an allowed list $U$. The two results which we expect to be most generally applicable are that (1) TRVB is polynomially solvable when breakable vertices are restricted to have degree at most $3$; and (2) for any $k \ge 4$, TRVB is NP-complete when the given multigraph is restricted to be planar and to consist entirely of degree-$k$ breakable vertices. To demonstrate the use of TRVB, we give a simple proof of the known result that Hamiltonicity in max-degree-$3$ square grid graphs is NP-hard. We also demonstrate a connection between TRVB and the Hypergraph Spanning Tree problem. This connection allows us to show that the Hypergraph Spanning Tree problem in $k$-uniform $2$-regular hypergraphs is NP-complete for any $k \ge 4$, even when the incidence graph of the hypergraph is planar.