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I was looking through a spreadsheet I created to compare my taxes this year and once I'm not working for money. Something I really hadn't thought of before was: What expenses will I have in retirement that won't be taxed? I know that my 401k/IRA withdrawals and the little bit of PBGC pension money won't have FICA/Medicare tax applied. But, does anything get special treatment from federal income tax?

Right now, the money I put into my 401k, the money I put into my HSA, and the money I pay for some benefits like health insurance and dental insurance, all come out pre-tax. Are there corresponding expenses in retirement that also get a tax deduction? I don't think that my health insurance premiums (pre-65 when I have to pay for the whole thing) or Medicare premiums (post-65) get any special treatment, but it seems worth asking.

Social Security gets taxed at 50% once you hit a certain total taxable income, and then 85% at another milestone, right?

If I use the HSA money to pay for Medicare premiums, it wouldn't be taxed, but I can use that money for the medical expenses themselves.
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