We report on a study undertaken to analyse AI performance on two tasks involved in automating processing of cases from the European Court of Human Rights: classification of legal case outcomes and keyword prediction. Results show variation across Articles and Court levels, and challenge the common viewpoint that larger legal corpora combined with larger models will be sufficient for effective automated legal reasoning. Legal summarisation, as reflected with keyword prediction, proved more challenging than outcome classification. Our results suggest the need for improved case law retrieval and understanding of contextual factors for effective automated legal decision support.