The context of territory-based innovation processes includes both barriers and incentives. This chapter presents the research and findings of a study conducted with two sets of five community-led initiatives, one composed of small-sized initiatives and another composed of larger-sized initiatives, with a view to identify barriers and incentives to territory-based innovation. Following a mixed-coding approach, data was analysed to identify barriers and incentives to territory-based innovation prompted by the use of digital tools, by the interaction among actors, and by contextual factors. Results from both types initiatives show significant technology weariness, still initiatives praise the effectiveness of some digital tools, namely social media, in reaching their audience. Both types of initiatives evidence disappointment towards cultural traits and bureaucracy, being these factors experienced as a disheartening barrier. Yet, initiatives also commend the know-how and flexibility of specific actors, with whom initiatives interact with closely when performing their activities.