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We ask a mechanism question rather than claiming a better general-purpose memory system: when does organizing trajectory memory into overlapping semantic units (OSUs) -- groups of related steps in which one step may belong to several units -- help retrieval over flat or disjoint alternatives? We instantiate this in OSU-Mem, which retrieves from an overlapping OSU pool via budgeted coarse-to-fine expansion, and show its benefit is conditional: overlapping memory helps when the evidence steps a query needs share tool calls or entities, but hurts when those steps are fully heterogeneous and share neither. On a synthetic benchmark where evidence carries such shared structur","title":"When Does Overlap Help? 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