Purpose: To investigate the medium-term survival of Dalbo-Rotex retention elements, identify potential risk factors for complication or loss, and consider economic factors. Materials and Methods: Patients treated with Dalbo-Rotex retention elements in a university setting were retrospectively identified and examined. Clinical data comprised assessments of the dental, periodontal, endodontic, and prosthetic situation, including radiographic analysis. Patient satisfaction was quantified with visual analog scale questionnaires. Five-year Kaplan-Meier plots for relative survival and success rates were calculated. Results: The 45 included patients had a total of 76 Dalbo-Rotex retention elements. Of these, 12 Dalbo-Rotex elements failed and complications occurred in 42.1% of elements, equating to a survival rate of 84.2% and a success rate of 47.4% after a mean observation period of 49.2 ± 52.4 months (range: 6 to 219 months). The 5-year cumulative survival and success rates were 62.4% (95% CI: 44.0% to 88.4%) and 35.6% (95% CI: 23.8% to 53.2%), respectively. Patients’ self-assessment of prosthesis retention was rated at 82 (IQR 40 to 92.2) with low pain perception at 4.5 (IQR 0 to 30). Probing pocket depth levels were significantly reduced in patients adhering to a regular recall interval compared with those with longer intervals. Conclusions: Chairside Dalbo-Rotex retention elements are a straightforward chairside method for prosthesis retention that achieve good survival over medium-term follow-ups with high patient satisfaction. This technique is therefore a viable alternative to cast post copings and can be particularly valuable for patients with limited financial resources.