Sticking oxide scale is one of the most serious concerns on moving steel surfaces at elevated temperature. However, there has been limited research dedicated to overcoming this issue. In the present work, pin-on-disc testing was carried out to reveal the effects of lubrication on wear characteristics of High Speed Steel sliding against Stainless Steel 316 at 700 °C. Apart from improved friction behavior, the use of inorganic lubricant significantly inhibits material transfer onto the HSS surface which otherwise suffers growing adhered scale during dry sliding contact. In addition, it was found that prolonged exposure to lubrication induces phase transformation of the subsurface iron oxides. The Hematite-to-Magnetite conversion is believed to be a result of complex oxidation and tribological reactions. Multiple characterization techniques were used to thoroughly analyze the worn surfaces, the underlying oxide microstructure and the chemical nature of lubricated interface.