The significant HCI interest in emotions is reflected in a breath of technologies and design approaches. This paper offers a brief overview of my HCI work on emotions, with a reflection on the outstanding challenges that future HCI agenda in this space should focus on. The latter emphases the need for stronger theoretical framing of emotions for interaction design, multisensory interaction for capturing and representing emotions, richer set of wearable bio sensors and actuators, operationalization of emotion regulation theories, and increased sensitivity towards the ethics of working with emotions as a resource for design.