After a medical consultation or hospitalisation, when the patient returns to everyday life, how is the correct adherence and therapeutic continuity guaranteed according to the indications given by the clinician, especially when it comes to multidimensional therapy (e.g. pharmacological, rehabilitation, etc.)? Do clinicians and hospitals use communication strategies and tools to give indications—through prescriptions—of sometimes complex therapies to be followed effectively? Moreover, what tools does the patient have to tell the general practitioner about the therapies in use or support therapy management at home? In the specific case of medicines, what dialogue is established between doctor and patient to assess the appropriateness of their prescription, considering not only clinical needs but also the patient’s lifestyle and preferences? The chapter addresses the process of transitioning care from the hospital to the home setting, presenting the different phases and issues that, on the medical side and the patient side, are experienced from the moment of prescription. The emerging reflections form the basis for formulating perspectives for future models of transition of care and discharge.