When Truncated Rankings Are Better and How to Measure That – Abstract⋆ Enrique Amigó1 , Stefano Mizzaro2 and Damiano Spina3 1 UNED NLP & IR Group, Madrid, Spain 2 University of Udine, Italy 3 RMIT University, Melbourne, Australia Abstract In this work we provide both theoretical and experimental contributions for the truncated ranking evaluation, where systems have a stopping criteria to truncate the ranking at the right position to avoid retrieving those irrelevant documents at the end. We first define formal properties to analyze how effectiveness metrics behave when evaluating truncated rankings. Our theoretical analysis shows that de-facto standard metrics do not satisfy desirable properties to evaluate truncated rankings: only Observational Information Effectiveness (OIE) – a metric based on Shannon’s information theory – satisfies them all. We then perform experiments to compare several metrics on nine TREC data sets. According to our experimental results, the most appropriate metrics for truncated rankings are OIE and a novel extension of Rank-Biased Precision that adds a user effort factor penalizing the retrieval of irrelevant documents. Keywords Information Retrieval, Evaluation, Evaluation measures, Ranking Cutoff CIRCLE (Joint Conference of the Information Retrieval Communities in Europe) 2022 is the second joint conference of the information retrieval communities, July 4-7, 2022, Toulouse, France ⋆ This work has been published at the SIGIR 2022 main conference. $ enrique@lsi.uned.es (E. Amigó); mizzaro@uniud.it (S. Mizzaro); mizzaro@uniud.it (D. Spina) € https://sites.google.com/view/enriqueamigo/home (E. Amigó); https://www.dimi.uniud.it/mizzaro (S. Mizzaro); https://www.dimi.uniud.it/mizzaro (D. Spina)  0000-0003-1482-824X (E. Amigó); 0000-0002-2852-168X (S. Mizzaro); 0000-0001-9913-433X (D. Spina) © 2022 Copyright 2022 for this paper by its authors. Use permitted under Creative Commons License Attribution 4.0 International (CC BY 4.0). CEUR Workshop Proceedings http://ceur-ws.org ISSN 1613-0073 CEUR Workshop Proceedings (CEUR-WS.org)