Digital transformation has potential for improving food security through agriculture development. While these transformations are welcomed and while societies are generally moving towards modernization and digitalization, farmers in the Global South have not been transitioning into the age of digitalization, and so are unable to take full advantage in ways that can enhance the agro value chain. Considering this, what may account for the sub-optimal take up from digital transformation deployment in agriculture sector in a small island developing state? Has there been any successes to the agriculture value-chain? What are the lessons to be learned? While the systems are available and farmers may have an interest in using them, their lack of ability to maneuver these new technologies leads to non-take up/use of the new beneficial technologies. A general distrust in government further compounded by a general distrust in the use of the internet has polarized farmers from digital technologies. The sluggish operations of governments of the South have inhibited the innovation that is required to enhance take up of digital technologies in agriculture. Privatization of digitalization in agriculture is therefore proffered as an alternative to a state-owned and state-operated digital transformation of agriculture. A policy options framework is proposed as a starting point to mitigating some of the challenges faced and improving digital transformation efforts in agriculture.