Among the many technologies competing for the Internet of Things (IoT), one of the most promising and fast-growing technologies in this landscape is the Low-Power Wide-Area Network (LPWAN). Coverage of LoRa, one of the main IoT LPWAN technologies, has previously been studied for outdoor environments. However, this article focuses on end-to-end propagation in an outdoor-indoor scenario. This article will investigate how the reported and documented outdoor metrics are interpreted for an indoor environment. Furthermore, to facilitate network planning and coverage prediction, a novel hybrid propagation estimation method has been developed and examined. This hybrid model is comprised of an artificial neural network (ANN) and an optimized Multi-Wall Model (MWM). Subsequently, real-world measurements were collected and compared against different propagation models. For benchmarking, log-distance and COST231 models were used due to their simplicity. It was observed and concluded that: (a) the propagation of the LoRa Wide-Area Network (LoRaWAN) is limited to a much shorter range in this investigated environment compared with outdoor reports; (b) log-distance and COST231 models do not yield an accurate estimate of propagation characteristics for outdoor-indoor scenarios; (c) this lack of accuracy can be addressed by adjusting the COST231 model, to account for the outdoor propagation; (d) a feedforward neural network combined with a COST231 model improves the accuracy of the predictions. This work demonstrates practical results and provides an insight into the LoRaWAN's propagation in similar scenarios. This could facilitate network planning for outdoor-indoor environments.