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But it's also worth noting that if they keep the employer-sponsored plan for the whole family, the premiums will almost certainly be payroll deducted on the pre-tax basis. On the other hand, if they opt to buy an individual market plan, the premiums would only be tax deductible to the extent that they (along with other medical expenses) exceed 10 percent of the family's household income, and assuming that the family opts to itemize their tax deductions (increasingly rare now that the Tax Cuts and Jobs Act has greatly increased the standard deduction).