Calcifying fibrous tumor (CFT) is a very rare benign fibroblastic tumor featuring a wide anatomical distribution and mimicking various spindle cell tumors. CFT has been documented in soft tissues, gastrointestinal tract (GIT), neck, adrenal glands, and pleura. Within the GIT, it is reported in the stomach, small bowel, large intestine, stomach, esophagus, and appendix. The occurrence of CFTs in the gastrointestinal tract presents a diagnostic dilemma, firstly due to the rarity of the lesion and secondly, due to the occurrence of a variety of other stromal lesions in the gastrointestinal tract with histological features that overlap with CFT. In the jejunum, it is extremely rare. We present one such rare case of jejunal CFT at an unusual age, complicated by jejuno-jejunal intussusception resulting in acute intestinal obstruction.