The sustainability concerns of the developed world together with increased tourism activities and migration have stimulated the growth and expansion of domestic and international High Value Markets (HVMs) of black pepper. This study is an attempt to identify the transactional attributes and farmer capabilities that influence the smallholder farmers’ willingness to participate in black pepper HVMs and to examine the novel vertical integration mechanisms that connect them to HVMs. The study is based on primary data from randomly selected 198 smallholder farmers from eight prominent black pepper growing Agro-ecological Units (AEUs) in Kerala. The factors influencing the smallholder farmers’ willingness to participate in black pepper HVMs were analysed in logistic regression framework. The trend analysis revealed the growth in black pepper cultivation area as well as export at national level, while a stagnation trend in area was observed at state level. A negative trend was observed in production as well as productivity at national and state levels. The results of percentage analysis of willingness of small holder farmers to participate in HVMs shows that 32.83% of smallholder farmers were willing to participate in black pepper HVMs . The farmer capabilities such as number of international linkages and digital literacy and transactional attributes such as asset specificity and number of verticals integrated were found to be significantly influencing smallholder farmers’ willingness to participate in HVMs. The study suggest that change agents may implement interventions to enhance the existing co-ordination mechanisms by exploiting the possibilities of digitisation and digital transformation. Also, efficient measures are required to protect farmers’ rights on the asset specific resources and to mitigate unfavourable agroecological transformations that hinder the production of site-specific assets that ensures sustainable value chain for black pepper high value products.