The vast amount of research introducing new corpora and techniques for semi-automatically annotating corpora shows the important role that datasets play in today’s research, especially in the machine learning community. This rapid development raises concerns about the quality of the datasets created and consequently of the models trained, as recently discussed with respect to the Natural Language Inference (NLI) task. In this work we conduct an annotation experiment based on a small subset of the SICK corpus. The experiment reveals several problems in the annotation guidelines, and various challenges of the NLI task itself. Our quantitative evaluation of the experiment allows us to assign our empirical observations to specific linguistic phenomena and leads us to recommendations for future annotation tasks, for NLI and possibly for other tasks.