We revisit a classical crossword filling puzzle which already appeared in Garey\&Jonhson's book. We are given a grid with $n$ vertical and horizontal slots and a dictionary with $m$ words and are asked to place words from the dictionary in the slots so that shared cells are consistent. We attempt to pinpoint the source of intractability of this problem by taking into account the structure of the grid graph, which contains a vertex for each slot and an edge if two slots intersect. Our main approach is to consider the case where this graph has a tree-like structure. Unfortunately, if we impose the common rule that words cannot be reused, we show that the problem remains NP-hard even under very severe structural restrictions. The problem becomes slightly more tractable if word reuse is allowed, as we obtain an $m^{tw}$ algorithm in this case, where $tw$ is the treewidth of the grid graph. However, even in this case, we show that our algorithm cannot be improved. More strongly, we show that under the ETH the problem cannot be solved in time $m^{o(k)}$, where $k$ is the number of horizontal slots of the instance. Motivated by these mostly negative results, we consider the much more restricted case where the problem is parameterized by the number of slots $n$. Here, we show that the problem becomes FPT, but the parameter dependence is exponential in $n^2$. We show that this dependence is also justified: the existence of an algorithm with running time $2^{o(n^2)}$ would contradict the randomized ETH. Finally, we consider an optimization version of the problem, where we seek to place as many words on the grid as possible. Here it is easy to obtain a $\frac{1}{2}$-approximation, even on weighted instances. We show that this algorithm is also likely to be optimal, as obtaining a better approximation ratio in polynomial time would contradict the Unique Games Conjecture.