Despite the rapid growth and potential for technology-based services from a technology and productivity perspective, the biggest challenges that managers often face are gaining customer acceptance and increasing usage of these new innovative services. In the B2C field, studies of self‐service technology show that the perceived risk is an important factor influencing the usage of service technology. Whereas research has explored different risk types that emerge in consumer settings such as functional and psychological risk, research on risk perception in B2B setting still lacks a detailed examination of the different facets risk can take on in technology-based service adoption. Some studies indicate that there might be different views and perceptions of the risk involved in technology-based services between customers and providers. Our study addresses this gap and aims to develop a holistic understanding of the types of risk customers perceive when using a technology-based service. We investigate what types of risk are emergent in technology-based service encounters and whether customers and providers perceive these risks differently. We conducted 49 qualitative interviews with providers and customers in two industries in four countries. Our study emphasizes the importance of functional and financial risks as expected in a B2B context, but also sheds light on the fact that business customers have personal and psychological fears that hinder them from using technology-based services. Most importantly, we show that gaps in the perception and evaluation of risk exist between customers and providers: customers doubt the functionality of technology-based services; they emphasize privacy risk as a main hindrance and worry about their own role in a service, whereas only few providers are aware of the customers’ fears.