Why doesn’t my entry in box 5 of the 1099-R carry to Schedule A as a medical expense?
According to the instructions for Form 1099-R, box 5 may include any of the following:
- Designated Roth contributions or contributions actually made on behalf of the employee over the years under the plan that were required to be included in the income of the employee when contributed (after-tax contributions),
- Contributions made by the employer but considered to have been contributed by the employee under section 72(f),
- The accumulated cost of premiums paid for life insurance protection taxable to the employee in previous years and in the current year under Regulations section 1.72-16 (cost of current life insurance protection) (only if the life insurance contract itself is distributed), and
- Premiums paid on commercial annuities.
Because box 5 has multiple purposes, entries in that field on the 1099 screen do not automatically carry to Schedule A.
For more information, refer to the Instructions for Forms 1099-R and 5498.