Background: Prolactin (PRL) secreting tumors are the most common functional neoplasms of the pituitary and are commonly subdivided into microprolactinomas (<10 mm) and macroprolactinomas (≥10 mm) according to their baseline diameter. The diagnosis of macroadenomas is usually straightforward and these large tumors may be associated with mass effects such as severe headache, nerve palsies or visual changes. Hyperprolactinemia can be due to other causes like pregnancy, drugs, hypothyroidism, and pituitary stalk effect should be considered in the differential. Clinical Case: A 30 year female having symptoms of prolactinoma showing amenorrhea of 3 years, galactorrhea, decrease libido who presented to the clinic for headache recently associated with anxiety. Headache initially frequently with 2-3 times in a week, moderate intensity lasting few hours, on one side of head and sometimes on the forehead, associated with blurry vision. Patient was on oral contraception taking on and off, but not on any medication currently. Initial work up consistent with hyperprolactinemia: elevated prolactin level 737.6 ng/ml (n 3.0-30 ng/ml), however other pituitary hormones are within normal limit, ACTH 32 pg/ml (n 6-50 pg/ml),FSH 3.2 mid/ml, LH 0.3miu/ml, total testosterone 13 ng/dl (n 2-35 ng/dl),TSH 1.6 mid/l (N 0.35-3.7 mid/l), FT4 0.92 ng/dl (N 0.76-1.46 ng/dl), human growth hormone <0.1ng/ml (N <=7.1 ng/dl), random cortisol 14.6 ug/dl (N 4.3-22.4 ug/dl). Pregnancy test is also negative. MRI Brain with and without contrast revealed a mass within the pituitary fossa producing smooth depression of the floor and suprasellar extension just the right of midline producing mild impingement on the undersurface of the optic chiasm, craniocaudal dimension of the tumor approximately 1.85 cm by 1.8 cm mediolateral by 1.4 cm anteroposterior without encasement or diminution of carotid arteries flow. Within the sella there is a spherical collection of T1 high signal displaying a fluid level strongly concerning for hemorrhage within the pre-existing tumor. There is no prior CT Head or MRI Brain available. Ophthalmology evaluation showed normal dilated retinal exam and no visual field defects. Medical treatment with Cabergoline 0.25 mg PO twice weekly was given on the visit, however patient did not start it yet and repeat prolactin level with 629 ng/ml. Patient endorsed that headache is better with less frequent about once in two weeks but still with absence of menstruation. Conclusion: This is the case of prolactin secreting pituitary macroadenoma with the change in character of headache due to hemorrhage in the tumor, having gradual improvement of headache which may be due to spontaneous resolving of hemorrhage from the pre-existing pituitary mass. It is very important to inform the patient with pituitary tumor go to ED if there is change in headache or vision.​