<b><i>Background:</i></b> Self-expanding metal stents (SEMS) have been used for the palliative treatment of malignant gastrointestinal tract obstruction. However, restenosis or incomplete expansion of a first stent is a frequent complication, and the effectiveness of reintervention with placement of a second stent is still controversial. <b><i>Objective:</i></b> To evaluate the clinical outcomes of covered SEMS (cSEMS) placement after dysfunction of uncovered SEMS (uSEMS) by the stent-in-stent technique. <b><i>Patients and Methods:</i></b> We retrospectively studied a consecutive series of patients receiving palliative treatment for malignant gastrointestinal obstruction with cSEMS placement after uSEMS dysfunction in a tertiary center from January 2013 to August 2018. Technical and clinical success, time of patency, and adverse events were analyzed. <b><i>Results:</i></b> Twelve patients were included; their mean age was 60 ± 9 years. Eleven patients had gastric outlet obstruction, and 1 patient had compression of the transverse colon due to gastric neoplasia. In 5 cases, there was absence of early clinical success with uSEMS and stent dysfunction in 7 cases (median patency time: 81 days). There was 100% technical success and 91.7% clinical success after cSEMS placement. There were no adverse events nor need for reintervention. The median patency time after placement of both stents was 163 days (vs. 71 days with the initial stent). <b><i>Conclusion:</i></b> cSEMS placement after uSEMS dysfunction is technically feasible and a clinically effective treatment for patients with recurrent malignant gastrointestinal obstruction, with good stent patency in the medium/long term. This approach seems to be safe and without increase in adverse effects.