Solar energy harvesting is among the best solutions for a global transition toward carbon-neutral energy technologies. The existing solar energy harvesting technologies like photovoltaics (PV) and emerging molecular concepts such as solar fuels and molecular solar thermal energy storage (MOST) are rapidly developing. However, to realize their full potential, fundamental solar energy loss channels like photon transmission, recombination, and thermalization need to be addressed. Triplet–triplet annihilation mediated photon upconversion (TTA-UC) is emerging as a way to overcome losses due to the transmission of photons below the PV/chromophore band gap. However, there are several challenges related to the integration of efficient solid-state TTA-UC systems into efficient devices such as: wide band absorption, materials sustainability, and device architecture. In this article, we review existing work, identify and discuss challenges as well as present our perspective toward possible future directions.