The nature of the Taliban–al-Qaeda relationship has long been a major controversy among experts. Some argue that the Taliban and al-Qaeda are synonymous in many respects and that their ideology and objectives are closely intertwined. Some believe that this is a relationship of convenience or necessity for both groups, while others insist on deeper personal and ideological ties. Given this public discourse, the author analyzes the ambivalent relationship between al-Qaeda and the Taliban over the past 25 years, which has always been of business nature (comprehensive assistance in exchange for sanctuary), but never a political alliance. Al-Qaeda’s globalist plans to create a mythical caliphate have always contradicted the Taliban’s modest goals: to restore order in the country by pacifying corrupt warlords, to form an efficient government that enforces Sharia law, and to achieve international recognition. At the initial stage, the al-Qaeda leadership did not comply with the restrictions imposed on them by the Taliban and behaved independently, which resulted in foreign intervention and the loss of power. The author concludes that the strategic goals of al-Qaeda posed a direct threat to the nationally oriented goals of the Taliban. However, in the 2000s, the Taliban’s ties to al-Qaeda were important for spreading the insurgency in Afghanistan, although al-Qaeda’s military contribution on the battlefield was very modest. The author focuses on the weakening of opportunities and the degradation of the influence of al-Qaeda under powerful pressure from the coalition forces, the Afghan and Pakistani governments. In recent years, al-Qaeda, amid the victories of the Taliban, has begun to rebuild its positions in Afghanistan. The article shows the dependence of the al-Qaeda leadership, which has nowhere to hide, on the new regime in Kabul, which allows the Taliban to better control the militants of this terrorist organization.