Purpose: Building on entrepreneurial learning research, the purpose of this paper is to argue that the students participating in foreign entrepreneurial education programmes can have realistic entrepreneurial learning experiences. This research addresses two specific questions: how situated ambiguity induced by a foreign culture may contribute to contextual entrepreneurial learning in education, and whether ambiguity induced by cross-cultural situated experience can stimulate critical reflection and important learning outcomes in entrepreneurship and increase entrepreneurial self-efficacy (ESE). Design/methodology/approach: The authors adopted a phenomenological perspective in the research, and used focus group interviews and the critical incident technique to investigate Norwegian master's students' experiences of entrepreneurial learning in a long-term practice in an American startup. Findings: The empirical findings reveal that the students perceived the foreign cultural learning setting as imbued with ambiguity and uncertainty. However, as the students enhanced their understanding of the culture and entrepreneurial milieu through observations and co-participating, they managed to adapt and develop new strategies and methods to cope with the new environment. Eventually, the students became more entrepreneurial and developed their ESE. Practical implications: The research demonstrates how educators can design educational programmes that approach real entrepreneurial learning contexts. Nevertheless, the research also displays several ethical dilemmas that educators need to address. Originality/value: The study delineates a new concept for educational designs called situated ambiguity, which reinforces the essence of situated entrepreneurial learning with cross-cultural learning. This concept offers a promising avenue for educators to approach real entrepreneurial learning in both theory and practice.