In the HCI community, there is growing recognition that a reflective and empathetic approach is needed to conduct ethical research in sensitive settings with people who might be considered vulnerable or marginalized. At our CHI 2015 workshop on ethical encounters, researchers shared personal stories of the challenges and tensions they have faced when conducting HCI research in complex settings such as hospitals, with young mental health patients, in schools for children with disabilities, and with homeless people. These research contexts can present significant challenges for HCI researchers who would not typically receive the training that other professionals working in these environments would normally receive. From our discussions with attendees at the CHI 2015 workshop, we identified a number of ethical issues that researchers are grappling with. In this follow-up workshop we aim to build on the lessons learned and to generate pragmatic but sensitive solutions to manage complex ethical issues for HCI researchers working in challenging settings.