It is commonly accepted that the autogenous self-healing of concrete is mainly controlled by the hydration of Portland cement and its extent depends on the availability of anhydrous particles. High-performance (HPCs) and ultra-high performance concretes (UHPCs) incorporating very high amounts of cement and having a low water-to-cement ratio reach the hydration degree of only 70–50%. Consequently, the presence of a large amount of unhydrated cement should result in excellent autogenous self-healing. The main aim of this study was to examine whether this commonly accepted hypothesis was correct. The study included tests performed on UHPC and mortars with a low water-to-cement ratio and high cement content. Additionally, aging effects were verified on 12-month-old UHPC samples. Analysis was conducted on the crack surfaces and inside of the cracks. The results strongly indicated that the formation of a dense microstructure and rapidly hydrating, freshly exposed anhydrous cement particles could significantly limit or even hinder the self-healing process. The availability of anhydrous cement appeared not to guarantee development of a highly effective healing process.