Sentiment analysis in social media is a popular task attracting the interest of the research community, also in recent evaluation campaigns of natural language processing tasks in several languages. We report on our experience in the organization of SENTIPOLC (SENTIment POLarity Classification Task), a shared task on sentiment classification of Italian tweets, proposed for the first time in 2014 within the Evalita evaluation campaign. We present the datasets -which include an enriched

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... scheme for dealing with the impact of figurative language on polarity -the evaluation methodology, and discuss the approaches and results of participating systems. We also offer a reflection on the open challenges of state-of-the-art systems for sentiment analysis of microblogging in Italian, as they emerge from a qualitative analysis of misclassified tweets. Finally, we provide an evaluation of the resources we have created, and share the lessons learned by running this task for two consecutive editions.