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As the aging population grows, chronic illness increases, and our healthcare costs sharply increase, patient portals are positioned as a central component of patient engagement through the potential to change the physician-patient relationship and enable chronic disease self-management. A patient’s engagement in their healthcare contributes to improving health outcomes, and information technologies can support health engagement. In this chapter, we extend the existing literature by discovering design gaps for patient portals from a systematic analysis of negative users’ feedback from the actual use of patient portals. Specifically, we adopt a topic modeling approach, latent Dirichlet allocation (LDA) algorithm, to discover design gaps from online low rating user reviews of a common mobile patient portal, EPIC’s mychart. To validate the extracted gaps, we compared the results of LDA analysis with that of human analysis. Overall, the results revealed opportunities to improve collaboration and to enhance the design of portals intended for patient-centered care. Incorporating these changes may enable the technologies to have stronger position to influence health improvement and wellness.