Mortgages, student loans, credit cards: debt is a ubiquitous component of daily life in Canada. But our attitudes toward debt, and the people who incur it, are complex. Trustees at Work explores the role bankruptcy trustees play in determining who qualifies as a deserving debtor under Canadian personal bankruptcy law. When debt becomes unmanageable, the bankruptcy and insolvency system provides relief – though not to everyone. The architects of the system have restricted access to this benefit by developing methods to distinguish deserving from undeserving debtors. The idea of a deserving debtor is woven throughout bankruptcy law, with debt relief being reserved for those debtors deemed deserving. The legislation and case law invite trustees to assess debtors based on their pre-bankruptcy choices, but in practice, trustees evaluate debtors based on how cooperative the debtors are during bankruptcy proceedings. Using insights from the sociology of emotion, Anna Jane Samis Lund reveals how carrying out emotional labour shapes an insolvency professional’s assessments of a debtor’s deservingness. Trustees at Work also includes interviews and statistical data to explain how the financial and emotional pressures of trustees’ work shape their decision-making process. Ultimately, it shows how insolvency trustees’ conceptions of a deserving debtor are shaped by the financial, legal, and emotional contexts in which they work.