The view of evaluating Strategic Information Systems Planning (Grover & Segars, 2005) process and effectiveness has matured. However, the inter-organizational view or network view is understudied. The introduction of information strategy in networks seems more reactive than proactive; many organizations continue to use SISP as a way to support their internal decision-making process without actually cooperating with their business partners. This article aims to qualitatively explore and validate, respectively, context and process dimensions in two inter-organizational cases: a network of municipalities in Finland and a network of healthcare organizations in the Netherlands. The first case study explores the network context and theorizes how network context influences inter-organizational SISP, discovering that the inter-organisational SISP process is influenced by the context, especially by the role of trust and complexity. The second case study is the exploration of three process dimensions: contingency, certainty and contractual agreements.