Vortices circulating in a ring made from a Josephson array in the insulating phase are studied. The ring contains a ‘dual Josephson junction’ through which the vortices tunnel. External non-classical microwaves are coupled to the device. The time evolution of this two-mode fully quantum mechanical system is studied, taking into account the dissipation in the system. The effect of the quantum statistics of the photons on the quantum statistics of the vortices is discussed. Entropic calculations quantify the entanglement between the two systems. Quantum phenomena in the system are also studied through Wigner functions. After a certain time (which depends on the dissipation parameters) these quantum phenomena are destroyed due to dissipation.