Perhaps better enlarged

The south barbican consists of a central twin-towered gatehouse, originally approached across a drawbridge, flanked by curtain walls with rounded towers at either end. The barbican was built between 1277 and 1285. The gatehouse passage had a portcullis with a double-leaf wooden door behind. Some arrow slits remain - others were later widened into windows.

in the 1570's the exterior of the gatehouse and its entrance passage were rebuilt. The carved masonry of the passage might be medieval material reused from Rievaulx Abbey. A craving of an imp on the right-hand side was perhaps placed there to ward off evil spirits. Originally the barbican towers were open at the back, but they were enclosed when the castle underwent major refurbishment during the late 13th to early 14th centuries.

The defences were not dismantled following the Civil War siege of Helmsley in 1644, and were probably retained to form an impressive approach to the Elizabethan mansion within the inner bailey.