Accurately estimating the six degree of freedom (6-DoF) pose of objects in images is essential for a variety of applications such as robotics, autonomous driving, and autonomous, AI, and vision-based navigation for unmanned aircraft systems (UAS). Developing such algorithms requires large datasets; however, generating those is tedious as it requires annotating the 6-DoF relative pose of each object of interest present in the image w.r.t. to the camera. Therefore, this work presents a novel approach that automates the data acquisition and annotation process and thus minimizes the annotation effort to the duration of the recording. To maximize the quality of the resulting annotations, we employ an optimization-based approach for determining the extrinsic calibration parameters of the camera. Our approach can handle multiple objects in the scene, automatically providing ground-truth labeling for each object and taking into account occlusion effects between different objects. Moreover, our approach can not only be used to generate data for 6-DoF pose estimation and corresponding 3D-models but can be also extended to automatic dataset generation for object detection, instance segmentation, or volume estimation for any kind of object.