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Open source communities hosted in large foundations operate in a complex socio-technical ecosystem, which includes a heterogeneous mix of projects and stakeholders. Previous work has thus far investigated the challenges faced in OSS communities from the point of view of specific stakeholders, primarily at the level of individual projects. None have yet studied the challenges faced within a large, federated open source organization. In this paper, we aim to bridge this gap to identify ongoing challenges contributors face in a mature OSS organization. To do so, we surveyed 624 contributors at the Apache Software Foundation (ASF) and ran 11 semi-structured follow up interviews. We validated our findings through member checking with the interviewees as well as the ASF Diversity and Inclusion (D&I) committee. The contributions of this paper include: (1) an empirically-evidenced conceptual model of the 88 challenges that contributors face in a mature OSS foundation and (2) a set of 48 community-recommended strategies for alleviating these challenges. Our results show that even well-established and mature organizations still face a variety of individual and project-specific challenges and that it is difficult to design a comprehensive set of processes and guidelines to match the needs and expectations of a diverse and large federated community. Our conceptual challenges model and associated strategies to mitigate them can provide guidance to other OSS foundations and projects helping them in building better support processes and tools to create a successful, thriving community of contributors.