This article discusses situations in which an evaluating physician may find rating according the AMA Guides to the Evaluation of Permanent Impairment (AMA Guides) cumbersome, including fingertip injuries, transection of flexor digitorum sublimis tendon, medial and lateral epicondylitis, upper extremity amputations, and recurrent shoulder dislocation. On finding decreased motion at a finger distal interphalangeal joint (DIP) or thumb interphalangeal (IP) joint, the examiner should carefully assess the functional consequences and ensure the rating adequately addresses the impairment but does not rate the same problem twice. Laceration of the distal palm or proximal phalanx of a finger resulting in isolated transection of the flexor digitorum sublimis tendon (flexor digitorum profundus tendon remains intact) is a challenging scenario. Medial and lateral epicondylitis are not mentioned in the AMA Guides because usually they resolve with time. Grip strength loss usually is not an appropriate way to rate epicondylitis because pain limits grasp in this condition. Impairment ratings for upper extremity amputations may not be consistent in terms of the location where the procedure is used. Recurrent shoulder dislocation may complicate an initial traumatic dislocation, particularly in younger patients and must be medically documented rather than anecdotally reported. When faced with a situation that is not covered in the AMA Guides, the rating physician should consider analogous situations, consult other manuals or guidelines, or discuss the case with other experienced evaluators.