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The present study proposes an innovative approach that combines five prospective label\u2010free methodologies (derivative spectroscopy, synchrotron small\u2010 and wide\u2010angle X\u2010Ray scattering, attenuated total reflection\u2013Fourier\u2010transform infrared spectroscopy, quartz\u2010crystal microbalance with dissipation, and surface plasmon resonance) to showcase their synergistic capabilities and complementarity in investigating drug\u2013membrane interactions. This multitechnique approach combines the real\u2010time monitoring of the adsorption process under continuous flow conditions with the steady\u2010state perspective of this process. As a proof of concept, the interaction of three bioactive compounds (caffeine, testosterone, and diclofenac) with two biomimetic membrane interfaces (multistacked lipid bilayers and supported lipid bilayers) mimicking the more ordered lipid transient phases, with and without cholesterol (<jats:italic>l<\/jats:italic><jats:sub>o<\/jats:sub> and <jats:italic>s<\/jats:italic><jats:sub>o<\/jats:sub>), that are responsible for a variety of membrane\u2010associated biological activities, is investigated. 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