To have a Part D plan that covers the gap, the person must also have Medicaid. That's the only way to not have a donut hole. Then, you would need to enroll in a benchmarked plan. The benchmarked plans for each state are on CMS' website. Enrollment time is November 15th through December 31st each year. That's the best time to sign up for a plan. If you don't sign up then, you can enroll any time, but coverage won't start until the first of the next month.