Earphone positioning and retention

Earphone positioning and retention mechanisms are disclosed. One earphone described includes a speaker driver, a flexible eartip comprising a first oval shaped contact surface at an opening forming a hole through the eartip, the first oval shaped contact surface configured to contact an outer surface of a user's ear canal when worn, a body portion comprising a second contact surface configured to position behind an anti-tragus portion of the user's ear, and, a retaining member formed of a compliant material, comprising a third contact surface configured to conform to a cymba conch portion of the user's ear, where the body portion and the retaining member are shaped in a way that the second contact surface contacts the anti-tragus portion and the third contact surface contacts the cymba conch portion at the same time, when the first contact surface is already in contact with the outer surface of the ear canal.