This article builds from scholarship in Environmental and Sustainability Education and Critical Global Citizenship Education calling for more explicit attention to how teaching global issues is embedded in the colonial matrix of power (Mignolo, 2018). It reports on findings from a small exploratory study with sec-ondary and upper secondary school teachers in England, Finland, and Sweden who participated in work-shops drawing on the HEADSUP (Andreotti, 2012) tool. HEADSUP specifies seven repeated and inter-secting historical patterns of oppression often reproduced through global learning initiatives. Teachers dis-cussed the tool and considered how it might be applied in their practice. The paper reviews two of the key findings from their discussions: a) the mediation of charity discourses and global-local relations and b) emerging evidence of how national policy culture and context influence teachers’ perceptions in somewhat surprising ways.