The world is increasingly using sanctions to achieve the economic and political goals of their initiators. They tend to target key sectors of the economy, including trade and finance. Sanctions are also applied to individuals and companies. At the same time, agriculture and food security are formally exempted from restrictions on humanitarian grounds, but are still negatively affected because they are an integral part of the economy. In many countries, the effects of sanctions are compounded by other factors of internal instability, such as military conflicts, natural disasters, and mismanagement. This article analyzes the dynamics of agricultural production, the use of production inputs and some indicators of food security in five countries under sanctions pressure (Iran, Syria, Venezuela, Cuba, and the Democratic People’s Republic of Korea). The aim is to analyze the development of the agricultural sector in these countries under sanctions. It is found that sanctions are a severe blow to the economy, including agriculture, but do not affect regime change, which is the ultimate goal of their initiators. The impact of sanctions is amplified in the case of secondary sanctions and the creation of a broad coalition. Moreover, the simultaneous application of financial and trade sanctions has a more pronounced negative effect. In addition to internal instability, sanctions significantly raise the composite Global Hunger Index, increasing the level of undernourishment in a country and negatively affecting the availability and stability of food supplies, while also increasing import dependence and food prices. In all the countries analyzed, the combination of constraints has led to a decline in agricultural productivity and access to resources, which has reduced agricultural production. At the same time, the industry is demonstrating its ability to adapt to prevailing conditions.