The digitalization of agriculture is rapidly changing the way farmers do business. With the integration of advanced technology, farmers are now able to increase efficiency, productivity, and precision in their operations. Digitalization allows for real-time monitoring and management of crops, leading to improved yields and reduced waste. This paper presents a review of some of the use cases that digitalization has made an impact in the automation of open-field and closed-field cultivations by means of collecting data about soils, crop growth, and microclimate, or by contributing to more accurate decisions about water usage and fertilizer application. The objective was to address some of the most recent technological advances that are leading to increased efficiency and sustainability of crop production, reduction in the use of inputs and environmental impacts, and releasing manual workforces from repetitive field tasks. The short discussions included at the end of each case study attempt to highlight the limitations and technological challenges toward successful implementations, as well as to introduce alternative solutions and methods that are rapidly evolving to offer a vast array of benefits for farmers by influencing cost-saving measures. This review concludes that despite the many benefits of digitalization, there are still a number of challenges that need to be overcome, including high costs, reliability, and scalability. Most of the available setups that are currently used for this purpose have been custom designed for specific tasks and are still too expensive to be implemented on commercial scales, while others are still in their early stages of development, making them not reliable or scalable for widespread acceptance and adoption by farmers. By providing a comprehensive understanding of the current state of digitalization in agriculture and its impact on sustainable crop production and food security, this review provides insights for policy-makers, industry stakeholders, and researchers working in this field.