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Explore the challenges and lessons learned from organizing seven virtual Ansible Contributor Summits during 2020-2022. Gain insights into the flexibility and obstacles of online events, including pre-event marketing, technology selection, and post-event feedback processes. Discover the shift towards using open-source tools and workflows for summit management, and understand how these changes impacted both the organizing team and Ansible contributors. Examine the implications for future in-person and hybrid events, and learn how to apply these experiences to improve conference planning and management as the industry transitions back to physical gatherings.