An elderly patient presented with acute-onset right-sided weakness and aphasia. A large penumbra was noted in the left middle cerebral artery (MCA) territory without any infarct core. The patient was noted to have a carotid–carotid bypass. This posed certain technical challenge in accessing the intracranial circulation across the carotid bypass; however, the guiding catheter with soft distal segment was successfully navigated coaxially over the aspiration catheter across the bypass and intracranial circulation was accessed for mechanical thrombectomy. Complete recanalisation and reperfusion were achieved with significant neurological recovery of the patient post-thrombectomy. The aim of this report is to emphasise on this rarely encountered situation in thrombectomy and its successful management. The procedure should not be delayed or deferred due to lack of operator experience.