Background and Aim: The recent rise in olive oil prices due to production shortages over the last two seasons has increased the risk of counterfeiting activities, particularly in unregulated markets where consumer protection is weak. This study aimed to investigate the prevalence of adulterated and/or misclassified olive oils sourced from these markets, thereby highlighting the associated risks to consumer safety and product authenticity. Methods: This study engaged the academic community in the Faculty of Pharmacy, leading to the collection of over 30 samples marketed as “extra virgin olive oil” (EVOO) from various unregulated sources, often unlabeled. Parameters assessed, in accordance with international guidelines, included free acidity and ultraviolet spectrophotometric analysis (COI/T.20/Doc nº 34 and 19, respectively) for olive oil categorization, as well as both fatty acids (COI/T.20/Doc nº 33, by GC) and vitamin E (ISO 9936:2016, by HPLC) profiles for authenticity. Results: Over half of the samples were not authentic, corresponding to unlabeled mixtures with vegetable oils. Among those identified as olive oil, the majority failed to meet the specifications for any commercial category due to excessive oxidation. Some mixtures with vegetable oils also had very high levels of oxidation. Interestingly, some samples were correctly labeled mixtures of vegetable oils and olive oil, overlooked by consumers, indicating a lack of awareness. Conclusions: These findings show how challenging it is to obtain authentic olive oil outside the regulated market. There is a critical need for enhanced consumer education and awareness regarding the risks of purchasing from these sources. Additionally, stricter regulatory oversight and quality control measures are necessary to protect consumers from health risks and economic fraud. Potential solutions include public awareness campaigns, stronger labeling requirements, and stricter penalties for fraudulent practices.