Medical bills are deductible on your tax return when the provider is paid. (That means that if you paid the provider with a credit card in 2023, and paid off the card in 2024, it would be a 2023 deduction.)
You should not take a deduction for any expense that was covered by insurance.
Insurance payments are not taxable income unless you previously took a deduction for an expense that was later reimbursed. In that case, you have a reimbursement of a previous deduction, and you need to use the tax benefit rule to determine if the reimbursement is taxable. We can give you more details about that if needed.
