Assessing the reliability of perception models to covariate shifts and out-of-distribution (OOD) detection is crucial for safety-critical applications such as autonomous vehicles. By nature of the task, however, the relevant data is difficult to collect and annotate. In this paper, we challenge cutting-edge generative models to automatically synthesize data for assessing reliability in semantic segmentation. By fine-tuning Stable Diffusion, we perform zero-shot generation of synthetic data in OOD domains or inpainted with OOD objects. Synthetic data is employed to provide an initial assessment of pretrained segmenters, thereby offering insights into their performance when confronted with real edge cases. Through extensive experiments, we demonstrate a high correlation between the performance on synthetic data and the performance on real OOD data, showing the validity approach. Furthermore, we illustrate how synthetic data can be utilized to enhance the calibration and OOD detection capabilities of segmenters.