The wine industry is a strategic sector in many countries worldwide. High revenues in the wine market typically result in higher investments in specialized equipment, so that producers can introduce disruptive technology for increasing grape production and quality. However, many European producers are approaching retirement age, and therefore the agricultural sector needs a way for attracting young farmers who can assure the smooth transition between generations; digital technology offers an opportunity to fulfill both needs in commercial vineyards. In this scenario, agricultural robots emerge as a novel approach to monitor key agronomical parameters and carry out specific agricultural operations. With the aim of reducing the breech between technology and grape growers, Europe is strongly supporting the practical application of new technologies and digital solutions in such a traditional crop as wine-producing vineyards. VineScout is an industry-driven consortium funded by the European Commission with the goal of industrializing previous prototypes developed under the EU project VineRobot. The Vinescout concept departs from a Technology Readiness Level (TRL) of 6/7, and is committed to yield a commercial prototype at TRL 9. The new robot is designed to be medium-size (100 kg), cost-efficient, and energy-saving with only electric drives, lithium batteries, and solar panels. This paper describes the advances carried out during the first year of the project, and how crucial challenges are being negotiated under a user-centered design. Assessing and mapping the spatial variability of vine water status in vineyards constitute a major challenge, especially in the current context of climate change. An effective, non-destructive, sampling system capable of providing a large amount of accurate observations is needed to define a sustainable irrigation scheduling. Field tests conducted over the summer in 2017 revealed the potential of automated monitoring for understanding water stress in vines. The VineScout robot was able to generate reliable temperature maps of the grapevine canopy in real time, non-invasively, and on-the-fly with a cost-efficient infrared radiometer.