Nautilus Minerals is the world leader in exploration and development of deep ocean seafloor massive sulphide (SMS) resources. The company is currently focused on generating its resource pipeline in the Western Pacific and its first development project for recovery of high-grade copper, gold and silver mineralisation from its Solwara 1 site in the Bismarck Sea, Papua New Guinea.The Solwara 1 site is located at a water depth of 1,600 -1800 meters. Over 150 SMS seafloor surface samples have been collected from chimney structures during dives made by remote operated vehicles (ROVs).In order to obtain an understanding of the sub-surface mineralisation, Nautilus carried out 3 drilling programs between 2006 and 2008 which allowed the calculation of a Canadian NI43-101 compliant resource estimate. The initial 2006 campaign was based on conventional offshore surface driven drill equipment. In conjunction with the subsea remote technology industry, Nautilus subsequently developed an ROV operated seafloor drill system with improved drill core recovery and efficiency. This technology was developed further with a 2010 drill program to increase the available geological knowledge at Solwara 1 and adjacent prospects. This paper will provide an overview of Nautilus' SMS drilling requirements and recap the evolution of drilling technology and operations undertaken at Solwara 1 from 2006 to 2010. The paper will also discuss the potential of further developments in drilling techniques and equipment to increase or improve drilling depth, efficiency and data quality.