Large language model (LLM) agents increasingly rely on external memory systems to remain consistent across long-horizon interactions, but little empirical work has been done to understand the specific failure modes and design choices that these systems present. Existing benchmarks report aggregate question-answering accuracy and treat memory systems as black boxes, making it impossible to attribute an incorrect answer to a particular failure mode of the system. We introduce MemFail, a diagnostic benchmark that isolates the failure modes of modern LLM memory systems. We begin by formalizing memory systems as the composition of three canonical operations -- summarization, storage, and retrieval -- and identify the potential failure modes induced by each. Based on these hypothesized failure modes, we construct five datasets spanning four tasks, each adversarially designed to test a specific operation of a memory system. Using these datasets, we evaluate four state-of-the-art memory systems on MemFail and demonstrate how MemFail can be used to empirically understand the tradeoffs induced by differences in memory system architectures.