This paper aims to demonstrate the viability of energy harvesting for wide area wireless sensing systems based on dye-sensitized solar cells (DSSCs) under diffuse sunlight conditions, proving the feasibility of deploying autonomous sensor nodes even under unfavorable outdoor scenarios, such as during cloudy days, in the proximity of tall buildings, among the trees in a forest and during winter days in general. A flexible thin-film module and a glass thin-film module, both featuring an area smaller than an A4 sheet of paper, were initially characterized in diffuse solar light. Afterward, the protype sensor nodes were tested in a laboratory in two different working conditions, emulating outdoor sunlight in unfavorable lighting and weather to reconstruct a worst-case scenario. A Li-Po battery was employed as a power reserve for a long-range wide area network (LoRaWAN)-based sensor node that transmitted data every 8 h and every hour. To this end, an RFM95x LoRa module was used, while the node energy management was attained by exploiting a nano-power boost charger buck converter integrated circuit conceived for the nano-power harvesting from the light source and the managing of the battery charge and protection. A positive charge balance was demonstrated by monitoring the battery trend along two series of 6 and 9 days, thus allowing us to affirm that the system’s permanent energy self-sufficiency was guaranteed even in the worst-case lighting and weather scenario.