A watercolour drawing of the Henry VIII Gateway from inside Windsor Castle, looking out towards the town. Several groups of figures are standing in the gateway: two soldiers, a man on horseback seen from behind and a street hawker with a basket and stick. A man, woman and child are standing below a bucket suspended on a chain held by a figure at the grille window at upper right. A board on the wall below reads 'Pray Remember the Poor Confin'd Debtors'. The sheet is circumscribed with a black ink line, and mounted on a yellow, pink and grey wash line border, a later reproduction of a mount usually associated with drawings acquired at the Paul Sandby estate sale in 1811.

A drawing of the same subject in ink and wash is in the Royal Collection (RCIN 914549), probably a preparatory study. As with other watercolours from the collection of Sir Joseph Banks, there is a related bodycolour version of the same subject (Courtauld Institute Galleries, Spooner Bequest, D.1967.WS.85). A pencil outline drawing of the Gateway is in the Staatliche Museen Greiz (E 456). A watercolour drawing of the Henry VIII Gateway from the other side, looking into the Castle, is in the Royal Collection (914548). As with this drawing, there is a related bodycolour version of the same subject (The Museum of New Zealand Te Papa Tongarewa, Wellington). Both bodycolours are dated 1767 and were possibly intended as a pair.

In the eighteenth century, the rooms over the Henry VIII Gateway were used as prison cells. The Debtor's Prison was removed between 1790 and 1805.