There has been a limited amount of research concerning culture and online education. Although human beings have the ability to transcend past and current environments, helping professions are recognizing the influence of cultural epistemologies on themselves and those they intend to serve. The purpose of this study was to explore the nature of additional challenges and concerns present when designing online instruction in a cross-cultural context. The data collected in this study stands as preliminary work to creating a substantive theory regarding the importance of cultural influences in the thinking, practice and lived experience of instructional designers, specifically those who have been creating cross-cultural online instruction. Twelve participants were chosen through a snowball sampling method, and case studies were constructing mainly through in-depth interviews. All of these participants were aware of cultural differences, although they recognized theirs was a limited awareness. Some of the many cultural differences these participants noticed in learner characteristics and expectations can be loosely separated into the following four categories: (a) technological infrastructure and familiarity, (b) general cultural and social expectations, (c) teaching and learning expectations, and (d) differences in the use of language and symbols. These participants became aware of cultural issues through both informal (unintentional) and formal (intentional) means. These participants felt a tension, however, between their desire to be more responsive to cultural differences, and the situations in which they were working. Three barriers to their ability to be as responsive to cultural differences were identified: (a) an over-focus on content development, (b) a relative lack of evaluation in real-world practice, and (c) the less than ideal roles instructional designers assume in the larger organizational structures involved. From this research, I present a bridge-building metaphor as a description of how an increased sensitivity to cultural differences influences can change the practice of instructional designers. Additional efforts are needed to educate and get buy-in from other stakeholders to engage in more learner analysis and evaluation. And additional models need to be used which put evaluation and learner feedback as a more integral part of the entire instructional design process.