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There is a dearth of research addressing network failures, and in particular failures of large-scale organizational networks that pursue radical innovation or grand challenges through collaboration. Yet these failures manifestly exist with potential learnings for network participants. In this chapter, the authors consider three major network failures that have been identified in prior research and in the ongoing empirical work. The authors term the failures stalling – not getting started in collaborative work, strategizing – using the network opportunistically to serve other goals than what the network was formed for, and siloing – the network falling short of its collective capacity to learn and innovate due to its lack of connectivity and communication. After describing these three seminal failures in networks of independent organizations, the authors consider the implications for high ambition network collaboration – whether radical innovation or a grand challenge. The authors ask: what do these failures suggest in terms of network participation that would help contribute to network realizing its objective? How should the individual participants of these large-scale organizational networks mitigate failure and maintain the founding ambition, and the performance of the network? What available models for learning are there for the network participants?