This chapter focuses on the issues that arise when prescribing opioids and other controlled substances for chronic headache pain. The majority of headache patients who overuse or develop dependence on opioids and opioid-containing compounds suffer from migraine-type headaches. Tramadol withdrawal often includes symptoms not typically seen in pure opioid withdrawal, such as extreme anxiety, panic or paranoia, hallucinations, and feelings of numbness and tingling in extremities. Butorphanol, an opioid with partial mu-agonist effects, was first developed in injectable form and initially used in hospital settings mainly for post-operative and labor pain. The only barbiturate indicated specifically for the treatment of headache is butalbital, prescribed in the various combination medications. The care of cannabis-using patients may be managed best by coordinating their continuing headache care with an addiction specialist. It is well known that patients with physiologic dependence on caffeine routinely develop caffeine withdrawal headaches.