This study sought to understand the extent of digital technology usage across Zambezi riparian countries and analyze whether there is a conducive enabling environment for digital technology upscaling for climate adaptation. The study thus, examined the relationship between having a better enabling environment and the use of digital technologies in agriculture. Using data collected through stakeholder consultations in Malawi, Mozambique, Zambia and Zimbabwe as well desk studies focusing on the rest of the Zambezi riparian countries (Angola, Botswana, Malawi, Mozambique, Namibia, Tanzania, Zambia and Zimbabwe, the study finds that having an enabling environment for the upscaling of digital technologies varies from one Zambezi riparian country to the other, with Botswana and Namibia, having a better enabling environment and, thus a better readiness for digital technology upscaling. Malawi, Mozambique, and Tanzania have enabling environments that beg for improvement to facilitate large scale adoption and upscaling of digital technology. Other key constraints that undermine the adoption and use of digital technologies across the Zambezi River Basin countries are related to availability, access, affordability, technology design, ease of doing business, cultural and family norms, gender, and poor user skills. The cost of data was observed to be one of the major constraints for digital technology use in climate change adaptation across several countries. Macroeconomic conditions, particularly inflation and lack of foreign exchange, also undermine growth prospects of digital technology adaptation as many of these technologies need to be imported. It is interesting that correlations between enabling environment indicators and digitalization variables appear to reveal a positive relationship signifying that to upscale the use of digital technologies in agriculture, it is critical to address parameters within the enabling environments including, pre-requisite infrastructure, macro-economic stability, policy, and regulatory environment.