Never tried imitrex prior to bedtime to prevent the headaches, nor treatment with estrogen. The regimen I am on (Indomethacin plus caffiene) was started by a headache specialist in San Fran,CA. Other meds for "hypnic" headaches did not work for me. While my regimen usually worked, my Mayo MD is hoping to ween me off Indomethacin since its not safe for long-term use (GI bleeding risk). I do take an additoinal med to help prevent GI bleeds called pantoprazole. I hope you can find safe treatments that are effective.