This session discusses the role of high-quality portrait photos in enriching Wikimedia Commons and augmenting Wikipedia articles and Wikidata items. We'll cover the complexities of mass-scale portrait photography at events, including challenges such as obtaining press credentials, release/consent, and licensing. By reviewing projects such as WikiPortraits Studios in North America and Festivalsommer in Germany, we hope to enrich your understanding of open media, and how you can bring similar initiatives to your community.