Attempts to construct string derived effective field theory models realizing large field inflation are plagued by control issues. Targeted at a broader audience, in this article we review recent progress in isolating the underlying conceptual reasons for this failure. Special emphasis is given to models of axion monodromy inflation and their relation to the Swampland Distance Conjecture. This discriminates effective actions that admit a UV completion, the landscape, from those that do not, the swampland. Since they are conceptually very similar, we also comment on implied challenges for axionic quintessence models.