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Introduction: Oral delivery is the most common administrated drug delivery path. However, oral administration of lipophilic drugs has some limitations: they have poor dose-response due to low and varied dissolution kinetics and oral bioavailability with sub-optimal dissolution within the aqueous gastrointestinal microenvironment. Therefore, there is a need for robust formulating methods that protect the drug until it reaches to its optimum absorption site, allowing its optimum pharmacological effects via increasing its intestinal permeation and bioavailability. Area covered: Herein, we provide insights on orally administered lipophilic drug delivery systems. The detailed description of the obstacles associated with the oral bioavailability of lipophilic drugs are also discussed. Following this, techniques to overcome these obstacles with much emphasis on optimal safety and efficacy are addressed. Newly designed ionic vibrational jet flow encapsulation technology has enormous growth in lipophilic drug delivery systems, which is discussed thereafter. Expert opinion: Researchers have shown interest in drug’s encapsulation. A combination of drug-bile acid and microencapsulation methods can be one promising strategy to improve the oral delivery of lipophilic drugs. However, the most critical aspect of this approach is the selection of bile acids, polymer, and encapsulation technology. © 2020 Informa UK Limited, trading as Taylor & Francis Group.