Marking of the Second Serbian Uprising fiftieth anniversary and the initiative to establish new decorations gave the reason for the engagement of artists in the development of their conceptual designs. Several artists worked on the sketches of a commemorative medal. Vincenzo Katzler's drafts were accepted, and Anastas Jovanović produced the final version based on the draft in the Vienna Mint by Wilhelm Pittner. The artistic design of this medal, in the form of a double portrait, was a novelty in the medal making of Serbia. On the obverse are the busts of Miloš and Mihailo Obrenović in ceremonial uniforms with decorations, framed with the inscription: PRINC MILOŠ OBRENOVIĆ AND PRINC MIHAILO III. It was a so-called numismatic type of portrait, taken over by ancient Renaissance culture through ancient models, governed by the belief that these facilitate memorising the physical appearance of the depicted character. The double portrait, a favourite in Renaissance political iconography and often used in the commemorative medals' design, expressed the idea of dynastic succession of power and continuity of ruling authority passed from father to son. The visual solution of the medal reverse is a composition of iconography with multiple meanings and a dominant representation of a woman personifying liberated Serbia, also featuring broken chains of slavery. The medal was made in several types of metal, and only the silver one had the character of a decoration that was awarded to the families of the insurgents. The only known specimen forged in gold is kept in the Belgrade National Museum.