This research is part of a study of a real-time, cloud-based on-street parking service using crowd-sourced in-vehicle fleet data. The service provides real-time information about available parking spots by classifying crowd-sourced detections observed via ultrasonic sensors. The goal of this research is to optimize the current parking service quality by analyzing the automation of the existing test process for ground truth tests. Therefore, methods from the field of machine learning, especially image pattern recognition, are applied to enrich the database and substitute human engineering work in major areas of the analysis process. After an introduction into the related areas of machine learning, this paper explains the methods and implementations made to achieve a high level of automation, applying convolutional neural networks. Finally, predefined metrics present the performance level achieved, showing a time reduction of human resources up to 99.58 %. The overall improvements are discussed, summarized, and followed by an outlook for future development and potential application of the analysis automation tool.