Probe systems for optically probing a device under test (DUT) and methods of operating the probe systems. The probe systems include a probing assembly that includes an optical probe that defines a probe tip and a distance sensor. The probe systems also include a support surface configured to support a substrate, which defines a substrate surface and includes an optical device positioned below the substrate surface. The probe systems further include a positioning assembly configured to selectively regulate a relative orientation between the probing assembly and the DUT. The probe systems also include a controller programmed to control the operation of the probe systems. The methods include methods of operating the probe systems.