This one-day workshop aims to contribute to the goals of the IFIP 13.6 Human Work Interaction Design (HWID) working group, i.e., to establish relationships between empirical work-domain studies and recent developments in interaction design. This goal translates to the workshop by focusing on work environments that are challenging for research and design; from physically or spatially unusual workplaces (e.g., oil platforms), mentally demanding or specifically boring work (e.g., control rooms, academics) to challenging social situations at work (e.g., in hospitals). The workshop aims to discuss resulting constraints for research and design, e.g., restricted access for research, or difficulties in articulating the specifics of the workplaces to a wider audience that is not familiar with them. Some work environments may even impede forms of design research, e.g., critical or provocative design will be hard to carry out in safety- or efficiency-critical workplaces. Thus, ways to generate knowledge addressing the design of interactive artifacts for challenging workplaces will be discussed.