This paper presents conceptual design and feasibility analysis for oversized grain harvesting combine headers with dynamic topology. To meet customer harvesting productivity requirements, the harvesting header must increase in width from 40 to 60 feet, yet be usable on current generation combine harvesters. While designing concepts for an oversized harvester head is a complex problem by itself, it also presents a latent challenge with packaging and transporting. Transporting a 60ft harvester header using traditional methods will violate road transport regulations imposed by US state and federal governments. This warrants innovations in both designing an oversized header concepts and viable means to package it for domestic and international shipping. The Advanced Systems Design Suite (ASDS) was used to design, visualize and perform quick assessment of the proposed concept designs. Three preliminary design concepts were generated based on customer requirements and manufacturer’s guidelines, of which one design was chosen for transitioning into detailed design stages. Static engineering analysis showed that the combine harvester’s feederhouse mount can support the additional mass of the larger header. Articulation mechanisms were represented by primitive shapes created in ASDS to visualize the preliminary design solution for packaging the header for transportation. Finite Element Analyses (FEA) was performed to determine the required size, shape, and position of the articulation mechanisms. Harvest productivity analyses were performed to assess business feasibility on the oversized header design. Header performance requirements identified potential time and monetary savings of an articulated header compared to a non articulated head of the same size. Reducing the time required to perform “non-harvesting activities” with currently available combines enables the manufacturer to generate a more feasible detailed design addressing this difficult design challenge. The ASDS, along with supplementary analyses tools can be used to generate viable design concepts and the work presented in this paper shows that the oversized combine header design is feasible and is worthy of transitioning into detailed design stages.