No. of Recommendations: 5
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

Actually, there are even various ways that these are 'pre-tax':

401(k) contributions are subject to OASDI (SS) and Medicare taxes (formerly known as FICA, which included both SS and Medicare). They can be either pre-tax (traditional) or post-tax (Roth and/or after-tax).

Payroll deductions for medical and dental insurance, as well as HSA, FSA and HRA contributions taken out of your paycheck and/or direct from your employer are free from OASDI, Medicare and income taxes.

HSA contributions you make from sources other than your paycheck or your employer are adjusted out of your income on the front page of the 1040, rather than having to be itemized deductions on Schedule A, but if the money you contribute came from your paycheck, it was subject to OASDI and Medicare taxes.

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.

Yes, if you itemize deductions, medical insurance premiums (along with other allowable medical expenses, and some long term care insurance premiums) are tax deductible on Schedule A, subject to a floor of 7.5% of your AGI (for 2017 and 2018) or 10% of your AGI (for 2019 and beyond). This deduction is available to everyone who pays these items from taxable money, not just to those who are no longer working. For employees who get their insurance as a benefit of employment, so any premiums are pre-tax, they generally don't reach the floor to take the deduction.

With the increase in standard deductions from the TCJA, it's likely that fewer people will be able to use the medical expense deduction, but it's still in the tax code.

Note: If you are not someone who regularly hits the OASDI earnings limit for SS taxes, there is a slight downside to having payroll deductions that are not subject to the 6.2% OASDI tax: that money is not counted as part of your lifetime earnings, so your SS benefit will probably be slightly smaller than it otherwise would have been. (Pay me now, or pay me later.)

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