Chorioamnionitis currently framed within the broader concept of intra-amniotic infection and/or inflammation is linked to preterm prelabor rupture of membranes (PPROM), preterm birth, maternal sepsis, and adverse neonatal outcomes. Diagnosis is largely clinical and requires close surveillance, particularly around the threshold of viability. We report a 32-year-old woman with a monochorionic diamniotic twin pregnancy at 23+4 weeks who presented with uterine-contraction like pain, vaginal bleeding, and watery vaginal leakage. On admission she was febrile (38.9 °C) with laboratory evidence of an inflammatory response; transvaginal ultrasound showed a normal cervix with a closed internal os and an anterior fundal placenta located >3 cm from the os. After a voluntary discharge, she re-presented with persistent fluid loss, abdominal pain, and marked leukocytosis. Repeat ultrasound demonstrated absence of fetal cardiac activity in both fetuses, leading to the diagnosis of retained twin miscarriage complicated by suspected intra-amniotic infection. Uterine evacuation was performed and inpatient management was completed. This case highlights the need for early recognition of suspected intra-amniotic infection criteria, optimized monitoring and counselling, and timely intervention to reduce maternal and fetal complications. [1–4]