The conference "Black Holes Inside and Out" will be devoted to the discussion of black hole physics in a broad sense. Its main aim is to bring together people working on theoretical, phenomenological, and observational aspects of classical and quantum black holes. Talks will cover foundational topics as well as recent theoretical and observational breakthroughs. Each session will consist of invited talks and ample discussion sessions. The conference will be held online on the Zoom platform from 27 September to 1 October 2021. Talks will be scheduled in the European afternoons to be as convenient as possible for all participants, as well as being recorded and posted online on the YouTube channel of the conference. This conference will be followed by the focused workshop "Regular black holes in quantum gravity and beyond - from theory to shadow observations" (Oct 18-22). We hope that while both online meetings can certainly be attended separately, participants as well as speakers can benefit from the proximity of the events, allowing them to continue discussions (including on the joint Slack space).