We present our experience with the implantation of flow diverter stents (FDSs) for the management of internal carotid artery (ICA) dissections in tortuous tonsillar loop segments. A total of 16 patients (10 women, 62.5%; mean age 39 ± 8 years; median baseline NIHSS 13; median ASPECTS 8.5) with acute ischemic stroke due to ICA dissection in a tortuous tonsillar loop segment, with/without large intracranial vessel thrombotic occlusion diagnosed between June 2015–February 2022 were included in this retrospective study under a waiver of informed consent. An FDS device was deployed from the petrous ICA toward the upper cervical ICA, completely covering the tonsillar loop. Stentriever-assisted thrombectomy was performed when indicated. A dual antiplatelet regimen was used during and after the procedure. Thrombocyte inhibition levels were evaluated before, during, and after the intervention. The ICA occlusion/near occlusion was successfully recanalized in all 16 patients with mean postangioplasty residual stenosis of 34 ± 14% (range 0–50%). Stent-assisted thrombectomy was performed in 15/16 patients (93.7%), achieving revascularization (TICI 2b–3) in all. There were no procedural complications and no intraprocedural embolic events; one asymptomatic petechial hemorrhage was detected. At 3-month follow-up, mRS 0–2 was seen in all patients. This report provides pilot data for a subsequent study on the use of flow diverter stents for ischemic cerebrovascular conditions. Our encouraging preliminary results await confirmation from further experience and prospective randomized studies.