Try this site where you can compare quotes from different companies: WWW.INSUREINFO.INFO Social security income and paying health insurance premium? My mother is receiving her social security early at 60 years old under widowed category. But is not getting medicare yet. So she is qualified for the low income health benefits. While being placed on the waiting list, she is purchasing the health plan at $302 a month. Can she claim this as a deductible when filing for taxes? Does she have to meet the 7.5% rule for medical expenses?