Stroke is an uncommon but serious potential complication of pregnancy. The management of acute ischemic stroke in pregnant women remains a complex challenge that extends beyond the limits of clinical trial evidence. Patient 1 was a 29-year-old woman 27 weeks into her first pregnancy, without remarkable past medical history or vascular risk factors. She was admitted 1 h after sudden onset of a left total anterior circulation syndrome (National Institute of Health Stroke Scale [NIHSS] score of 23). CT and angio-CT scans were normal. Thrombolysis was performed, with mild clinical improvement. Brain MRI showed multi-territorial embolic events. Extended blood panel, cervical-transcranial ultrasound, 48-h ECG monitoring, and transthoracic echocardiogram were unremarkable. She was started on aspirin and low-molecular-weight heparin (LMWH), giving birth to a healthy child 10 weeks later. Patient 2 was a 45-year-old woman 34 weeks into her pregnancy, without remarkable past medical history or vascular risk factors. She was admitted 30 min after sudden onset of a left partial anterior circulation syndrome, already partially recovered (NIHSS score of 4). The CT scan showed only a subacute right incidental middle cerebral artery infarct, while the angio-CT confirmed a left M3 branch occlusion. Thrombolysis and thrombectomy were contraindicated by the recent contralateral infarct, mild deficits, and distal occlusion site. Brain MRI also suggested an embolic etiology and LMWH was started. Extended blood panel, 48-h ECG monitoring, and transthoracic echocardiogram were normal. She gave birth to a healthy baby 4 weeks later. These cases emphasize the growing real-world evidence of the emergent use of CT, IV contrast, and recombinant tissue plasminogen activator in pregnant women with acute stroke, while also illustrating the importance of an individualized management, accounting for the safety of both mother and child.