People experiencing homelessness in the UK were unconditionally offered housing (and support) from the beginning of the first lockdown in March 2020. For many, that meant '(re)entering' the support system and having a chance to 'move on' to longer-term housing. This beneficial effect of some of the policy reactions to the pandemic on people experiencing homelessness was unexpected. On the flip side, however, particularly for people struggling with drug use and mental health issues, adequate support was not available for long periods of time; support was either suspended temporarily or people were excluded from institutional support for not adhering to, for instance, lockdown rules. Similarly, digital support alternatives-modelled on increasingly widespread telemedicine-did often not work specifically for people struggling with complex needs or women experiencing homelessness. This research paper reports detailed evidence of what we observed as continued and catalysed exclusions based on interviews and ethnographic observations with both people experiencing homelessness and service providers from the beginning of the COVID-19 pandemic. Referring to our insights and learnings from three locally and temporally overlapping research projects between May 2020 and April 2021, we also propose changes to redesign future (health)care provision to prevent such impasses-which extend beyond lockdown situations to general conditional housing and support.