Conventional removable dentures still play an important role in the treatment of lost teeth. A thorough understanding of the parameters that influence patient satisfaction is useful for deciding whether denture replacement is meaningful. From a clinical perspective, factors that can be measured before starting treatment are relevant. This pilot study investigated whether patient satisfaction after denture renewal was affected by aspects related to the old prostheses, type of jaw, and patient motivation for denture renewal. Fifty subjects (mean age 68.2 ± 8.4) were provided with 74 removable dentures (partial n = 20, complete n = 54). Satisfaction was assessed before treatment and 3 months after new prosthesis insertion. Total satisfaction 3-month post-insertion (TSP3) merged 6 individual satisfaction items measured after treatment. Change of total satisfaction 3-month post-insertion (CTS3) represented the difference of total satisfaction when old and new prostheses were compared. The effect of the following independent variables was investigated: reason patients requested new dentures (fit, esthetics, broken denture, wear, advice of dentist, extractions), satisfaction with the old prosthesis (general, retention, stability, comfort, pronunciation, chewing, esthetics), and technical quality of the old prostheses as assessed by a dentist (stability, retention, fit, border, wear, esthetics). Gender, age, and a cognitive screening test were included as confounding variables. Mann-Whitney-U tests and linear mixed model analysis were performed. All individual satisfaction items significantly improved with new prostheses for maxillary and mandibular jaws. TSP3 was higher for maxillary prostheses, if retention satisfaction with the old prosthesis was good, and if the dentist assessed the esthetics of the old prosthesis as deficient. CTS3 was associated with male gender, dissatisfaction with chewing before treatment, and dissatisfaction with esthetics before treatment. This pilot study showed that satisfaction 3 months after new denture insertion was associated with aspects of satisfaction and quality related to the old prosthesis, type of jaw, and gender. These factors may help dentists predict therapeutic benefits when deciding on the need for denture replacement. Further research should be done with a greater number of subjects and should include balanced quantities of the different types of dentures.