Bowel obstruction is a documented but rare presentation of adrenal insufficiency (AI). We report a case of acute AI manifesting as intestinal pseudo-obstruction (IPO) in a patient with underlying iatrogenic adrenal suppression. An 83 years old female was admitted for partial small bowel obstruction that failed to resolve with conservative management. She then underwent exploratory laparotomy where no mechanical obstruction was found and the small bowel was manually decompressed. Postoperatively she developed acute swelling of her right ankle which was similar to mono-articular attacks in the past. This was diagnosed clinically as gout. Her obstruction failed to settle and a second laparotomy was done which yielded the same as the first. Given her past account of arthritic pain, direct questioning of steroid use unearthed a history of multiple intra-articular corticosteroid injections for analgesia. She also described several short courses of high dose oral steroids for respiratory tract infections, including a recent course which was abruptly stopped two days prior to presentation. Clinical suspicion of AI was supported by biochemical testing of stress cortisol levels and change in the serum cortisol in response to 250 μg of synthetic adrenocorticotropic hormone. Moreover, her improvement following a therapeutic trial of steroid replacement was dramatic and strongly supports this diagnosis. It is therefore worthwhile to consider a diagnosis of AI in cases of bowel obstruction in patients with comorbidities that predispose to steroid use and especially in settings where steroid abuse is prevalent.