Spinal cerebrospinal fluid (CSF) leaks, including spontaneous intracranial hypotension (SIH) and post-dural puncture headache (PDPH), are important neurological disorders featuring rapidly evolving diagnostic and therapeutic tools. 1 Headache has recently advanced a strong focus on this area. 2,3 The diagnosis can be straightforward based on the clinical picture (spontaneous or post-procedure onset orthostatic headache) with radiological confirmation. However, challenging diagnostic conundrums manifest in clinical practice, particularly for CSF leak centers and other clinicians encountering complex presentations. Here, we frame three important scenarios requiring advanced clinical reasoning.