Gastrointestinal involvement is common in systemic sclerosis (SSc); however, intestinal pseudo-obstruction represents a rare and severe manifestation that may closely mimic mechanical small bowel obstruction (SBO). Differentiating functional pseudo-obstruction from true mechanical obstruction remains challenging due to overlapping clinical and radiological features, and recurrent presentations despite exclusion of an anatomic cause are uncommon. We report the case of a 66-year-old man with limited cutaneous SSc who presented with recurrent episodes of abdominal pain, vomiting, distension, and obstipation over a 24-month period. Cross-sectional imaging during multiple admissions consistently demonstrated features suggestive of mechanical SBO, including small bowel dilatation, apparent transition points, faecalisation, and ultimately a hide-bound appearance. Despite these findings, diagnostic laparoscopy revealed no mechanical obstruction. The patient experienced transient improvement with conservative management but had repeated re-presentations with progressively convincing radiological features. Management was further complicated by intolerance and limited response to multiple prokinetic agents. This case highlights an important diagnostic pitfall in which SSc-related intestinal pseudo-obstruction may present as a recurrent and progressively misleading radiological mimic of mechanical SBO, even after operative exclusion of a mechanical cause. Recognition of this entity is essential to avoid unnecessary surgical intervention and to facilitate appropriate conservative, nutritional, and multidisciplinary management. Clinicians should maintain a high index of suspicion for pseudo-obstruction in patients with SSc who present with recurrent obstructive symptoms, particularly when imaging findings are discordant with operative or clinical progression.