Constraints are part of any interaction design activity, as they inform as well as challenge and limit the designer. In this one-day workshop, we will discuss how constraints, which are resulting from their context, are fostering or hindering designs and the act of designing. Also constraints that have both positive and negative consequences will be addressed. The focus will be on limitations of how designers engage themselves with the context (e.g., in contextual design) as well as limitations on the design space as such (e.g., light conditions). Characteristics of constrained contexts might be their strict safety or security regulations, costly access, harsh conditions, temporal restrictions, rare existence, communication problems, etc. Examples for such heavily constrained contexts are environments like factories, cars and space ships, domains like finance and administration or seasonal events like New Year’s Eve and Christmas, but this list is almost interminable. With this workshop, we aim to address the assessment of types and forms of contextual constraints affecting design options and/or the respective design process. The vision is to better understand how to make use of the beneficial constraints for interaction design, and how to cope with hindering ones. We aim to collect experiences with contextual constraints, and seek to uncover design contexts that have so far rarely been in the focus of interaction design due to their hard approachability.