Public and nonprofit organizations often face various challenges when collaborating with others. The existing literature emphasizes the danger of collaborative challenges, and an implicit assumption is that collaborative challenges will affect inter-organizational relationships and network structures. Using data from three different purpose-oriented networks, this study explores the relationship between perceptions of collaborative challenges and network structure across the node, dyadic, and whole network level of analyses. The multi-case, multi-level analysis indicates that there is no pattern between perceived challenges and network structures. Organizations that perceive more challenges are not necessarily more resistant to work with other organizations. This counterintuitive null finding offers important implications for theory and practice. Network managers should be encouraged to embrace the complex or even paradoxical nature of collaboration. Emphasizing collaborative incentives may have greater impact than focusing on clearing challenges that are inherent in collaboration.