Loot boxes are popular random reward mechanisms in digital games, attracting players to invest real money to enhance their gaming experiences. Loot boxes share striking similarities to gambling and might contribute to one’s economic strain, but more research is needed on the underlying vulnerabilities and motivational traits in loot box purchasing. This paper examines associations with self-reported increase in loot box purchasing and debt problems during the first year of the COVID-19 pandemic. International survey data were collected in 2021, consisting of Finnish, Swedish, and British respondents (N = 2,991) aged 18 to 75. Partial least squares modeling was used as an analytical technique. The findings bring valuable insight into the underlying psychosocial and motivational factors in loot box purchasing and its association with indebtedness.