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How do drawings—ranging from detailed illustrations to schematic diagrams—reliably convey meaning? Do viewers understand drawings based on how strongly they resemble an entity (i.e., as images) or based on socially mediated conventions (i.e., as symbols)? Here we evaluate a cognitive account of pictorial meaning in which visual and social information jointly support visual communication. Pairs of participants used drawings to repeatedly communicate the identity of a target object among multiple distractor objects. We manipulated social cues across three experiments and a full replication, finding that participants developed object-specific and interaction-specific strategies for communicating more efficiently over time, beyond what task practice or a resemblance-based account alone could explain. Leveraging model-based image analyses and crowdsourced annotations, we further determined that drawings did not drift toward “arbitrariness,” as predicted by a pure convention-based account, but preserved visually diagnostic features. Taken together, these findings advance psychological theories of how successful graphical conventions emerge.