Online innovation communities allow for a search for novel solutions within a design space bounded by constraints. Past research has focused on the effect of creative constraints on individual projects, but less is known about how constraints affect learning from repeated design submissions and the effect of the technical constraints that are integral to online platforms. How do creative versus technical constraints affect individual learning in exploring a design space in online communities? We analyzed ten years of data from an online innovation community that crowdsourced 136,989 design submissions from 33,813 individuals. We leveraged data from two types of design contests-creatively constrained and unconstrained-running in parallel on the platform, and we evaluated a natural experiment where a platform change reduced technical constraints. We find that creative constraints lead to high rates of learning only if technical constraints are sufficiently relaxed. Our findings have implications for the management of creative design work and the downstream effects of the technical constraints of the information systems that support online innovation communities.