COVID-19 has upended the way analysts and psychotherapists practice. Many use the phone for their sessions, many are using video platforms, and many use a combination of the two. Work with adolescents is very challenging in this new modality because of the loss of in-person connection and immediate non-verbal cues. The public health restrictions put in place to manage COVID-19 spread are at odds with the adolescent tasks of adventuring, experimenting and gaining new experiences. In addition, increased anxieties about infection, contamination and invasion are often manifest and adolescents can regress in the face of them. Using seminal ideas from Bion, this article looks at two process examples from adolescent boys who struggled with parts of themselves that felt disturbing and unacceptable. The author discusses the clinical exchanges in detail and offers ideas about the difficulty of creating psychic space when working virtually.