Does a sebaceous cyst drain itself?

It can: If a sebaceous cyst, also known as an epidermal inclusion cyst, becomes inflamed enough it will drain on its own. They can be painful if inflamed. Do not try to squeeze it. If you want it removed, see your dermatologist as it is a routine surgical procedure.

Sebaceous cyst: Sometimes the contents of the sebaceous cyst gets hardened and will need to be surgically removed. The complete removal of the sac enclosing the cyst will prevent further recurrence.

Eh... it may. : It might rupture and feel. Better for a while. If you squeeze it You risk introducing infection and they have a likelihood of recurring. The cyst needs to be removed if bothering you. If not bothering you can be safely watched.