In many clinical cases a dentist may feel certain when for example diagnosing, deciding on treatment, or assessing the prognosis—in other cases many dentists may feel a degree of doubt or uncertainty. This paper aims to explore the philosophical concept of uncertainty and its different dimensions, using the condition “persistent apical periodontitis associated with a previously root filled tooth” as an example. Acknowledging that uncertainty exists in any clinical situation can be perceived as uncomfortable, as some might regard it as a weakness. Whilst some types of uncertainty met in dental practice can be addressed and reduced, there are other types which are inevitable and must be accepted. To make sound decisions, it is pertinent that the dentist reflects on and values the consequences of uncertainty. In this paper, a conceptual model is presented by which the dentist can identify the type of uncertainty in a clinical case, making it possible to decide on a strategy on how to manage the uncertainty and its possible consequences, with the aim to support the dentist's care for their patients. The understanding that uncertainty exists and the ability to acknowledge and be comfortable with it when making decisions should be addressed throughout our professional career, and thus ought to be developed during undergraduate education. Some suggestions on how teachers could target this are given in the paper.