A pen and ink and wash drawing of the Henry VIII Gateway at Windsor Castle, looking out towards the town. Groups of figures including a horse and cart on the left, soldiers beyond the gate, and a more animated group with a woman and child holding back a man from a basket being lowered from a window at upper right. A figure on the ground, possibly a child, is in pencil only. Inscribed below in pencil in the artist's hand: Town Gate Windsor Castle. On a wash line bordered mount. Stamped with EVII stamp in left corner (Lugt 901).

The drawing is probably a preparatory study for a more worked-up watercolour also in the Royal Collection (RCIN 914550), showing the Henry VIII Gateway from within the Lower Ward. 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. Sandby made several other versions of this subject, a watercolour in the Rischgitz collection (illustrated in Windsor Castle Views, vol. I, p. 56) and a bodycolour now in the Courtauld Gallery (Spooner Bequest, D.1967.WS.85) dated 1767, giving an approximate date for the present drawing. A watercolour drawing of the Henry VIII Gateway from the other side, looking into the Castle, is in the Royal Collection (RCIN 914548). As with the view from inside, 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.