Abstract This paper examines the transformative dynamics of civil society participation within the evolving political context of Lombardy, Italy, from 1992 to 2009. It revisits the neo-Tocquevillian thesis, interrogating the extent to which associations serve as "schools of democracy" or, alternatively, as mechanisms of socialization aligned with post-democratic conditions. By integrating macro-institutional perspectives and multi-level analysis, the study explores how associative participation intersects with party systems, governance structures, and political socialization. Research Question: How does participation in civil society organizations influence political socialization within a context of shifting party systems and post-democratic governance, and what mechanisms mediate these effects? Theoretical Framework: The paper builds on critiques of the neo-Tocquevillian thesis, incorporating theories of political socialization, institutional embeddedness, and post-democracy (Crouch, 2004). It introduces a contextual approach to examine how the socialization effects of associations are shaped by broader institutional and political shifts. Methodology: The research employs a mixed-methods design, combining survey data, participant observation, and in-depth interviews. Two longitudinal datasets (1992/93 and 2007/09) encompassing over 2,500 respondents provide a comparative basis for analyzing changes in associative participation and its political implications. Qualitative data from case studies and interviews with activists enrich the analysis, offering insights into the lived experiences of participants across diverse associative sectors. Content Overview: Revisiting the Neo-Tocquevillian Thesis: The first section critiques the universalist assumptions of the neo-Tocquevillian framework, arguing for a contextualized understanding of the political and institutional factors influencing associative participation. Participation in a Post-Democratic Era: This section explores the role of associations in the transition from democratic to post-democratic governance, examining their functions in lobbying, coalition-building, and symbolic representation. Empirical Analysis of Lombardy: Drawing on survey data, the paper highlights shifts in associative participation, political behavior, and trust in democratic institutions. It demonstrates how institutional reforms, such as regionalization and subsidiarity, have reconfigured the strategies and outcomes of civil society organizations. Mechanisms of Socialization: The final analytical section identifies key mechanisms mediating the relationship between associative participation and political socialization, including organizational strategies, group styles, and contextual factors. Conclusion: The paper concludes that while civil society participation retains political significance, its socialization effects are contingent upon institutional and political contexts. Associations do not universally promote democratic skills; instead, they reflect and reproduce the complexities of their environments, challenging the assumptions of traditional democratic theory.