The sustainable production of renewable energy is a key topic on the European community’s agenda in the next decades. The use of residuals from agriculture could not be enough to meet the growing demand for energy, and the contribution of vegetable oil to biodiesel production may be important. Moreover, vegetable oil can surrogate petroleum products in many cases, as in cosmetics, biopolymers, or lubricants production. However, the cultivation of oil crops for the mere production of industrial oil would arise concerns on competition for land use between food and non-food crops. Additionally, the economic sustainability is not always guaranteed, since the mechanical harvesting, in some cases, is still far from acceptable. Therefore, it is difficult to plan the future strategy on bioproducts production from oil crops if the actual feasibility to harvest the seeds is still almost unknown. With the present review, the authors aim to provide a comprehensive overview on the state of the art of mechanical harvesting in seven herbaceous oil crops, namely: sunflower (Heliantus annuus L.), canola (Brassica napus L.), cardoon (Cynara cardunculus L.), camelina (Camelina sativa (L.) Crantz), safflower (Carthamus tinctorius L.), crambe (Crambe abyssinica R. E. Fr.), and castor bean (Ricinus communis L.). The review underlines that the mechanical harvesting of sunflower, canola and cardoon seeds is performed relying on specific devices that perform effectively with a minimum seed loss. Crambe and safflower seeds can be harvested through a combine harvester equipped with a header for cereals. On the other hand, camelina and castor crops still lack the reliable implementation on combine harvesters. Some attempts have been performed to harvest camelina and castor while using a cereal header and a maize header, respectively, but the actual effectiveness of both strategies is still unknown.