One of the most mysterious likenesses of the last Polish monarch portrays him holding an hourglass, which relates to the final phase of monarchy beginning with the failure of the Third of May Constitution and invasion of Russian armed forces, followed by the king's humiliating endorsement of the Targowica Confederation. His allegorical portrait from around the beginning of 1793, after his withdrawal from public life, is assumed to represent one aspect of a royal apologia. The picture understood in this context was reproduced and presented to members of the royal family and supporters of the monarchy until the king's death in February 1798, and even later. The most important elements in the portrait's ideological expression are the crown and hourglass, placed in a specific configuration. On the basis of documentary sources it has been possible to establish that the crown symbolised abdication. The original shape of the insignia alludes to Christ's crown of thorns as well as Stanislaus Augustus's rule, fraught with difficulties and suffering, as confirmed by numerous statements made by the king himself. On the basis of the considerations contained in this article, the picture of Stanislaus Augustus with an hourglass appears as a portrait with no analogy in early-modern iconography, and the only likeness of its kind of an unhappy king.