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Adhesion of circulating cells to endothelial cells (ECs) lining blood vessels is a critical event in the multistep process of cell recruitment from the bloodstream into tissues, occurring in both homeostasis and pathological conditions. This chapter provides a comprehensive review of live-cell imaging methodologies for investigating leukocyte and cancer cell adhesion to endothelial cells (ECs), key processes in inflammation and metastasis. It outlines the biological significance of cell adhesion under shear stress, highlighting how real-time visualization has advanced understanding of molecular mechanisms governing immune cell recruitment and cancer dissemination. Early microscopy studies established foundational knowledge, while modern in vitro human models now enable high-resolution, physiologically relevant analysis of dynamic cell–cell interactions. For leukocytes, the chapter details imaging approaches that capture multistep adhesion cascades, including rolling, arrest, and transmigration, using static, flow-based, and microfluidic systems. Technologies such as the microfluidic devices and advanced microscopy have enhanced spatiotemporal resolution and minimized phototoxicity, while machine learning and label-free imaging are transforming quantitative analysis. Similarly, cancer adhesion imaging has evolved from static assays to microfluidic and organ-on-chip models that replicate vascular environments. Studies employing confocal, fluorescence, and label-free microscopy reveal how adhesion molecules, shear forces, and endothelial activation govern tumor cell arrest, invasion, and metastasis formation. The chapter concludes by emphasizing the transition toward human-relevant, three-dimensional, and computationally integrated systems. It advocates for combining organ-on-chip platforms with advanced microscopy and deep-learning analysis to overcome current imaging limitations and enhance translational relevance in inflammation and cancer research.