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You entered the data for the 2024 tax return correctly. You entered the dollars contributed in 2025 for 2024 in the "personal" contributions on your 2024 tax return. Good!   But, you should not have checked: "Checked box for "had other company contributions that weren't reported to their W-2 or apply to a previous year" because I had contributions in 2025 that apply to 2024, as stated." Why? Because the $3,650 contributed in early 2025 were not company contributions, they were personal contributions. This check box is only for amounts that should have been reported with a code of W but which for one reason or another, weren't. You were adjusting the code W amount for 2025, when, in fact and if I understand your situation correctly, the 4,300 in box 12 with a code of W on your 2025 W-2 was ALL intended for 2025, not 2024.   "My deduction should be 3800". But you said earlier that "I contributed 3800 in via payroll in calendar year 2025." If so, that 3800 was part of the code W amount in box 12. No part of this can be considered a "personal" contribution, no matter than you chose to contribute it or not. It's called an "employer" contribution because of how it is handled, not because of where it came from. Yes, very confusing, but that's the IRS for you.   So your deduction for 2025 should be zero. You get the tax benefit for the code W amount because before the W-2 is printed, the code W amount was removed from Wages in boxes 1, 3, and 5. So the company's 500 and your 3,800 were never in your income at all.   As an added bonus, because of the way the employers contribution is treated, you don't pay any SS tax or Medicare tax on it, whereas you do pay those taxes on your "personal" contribution.   P.S. if you are ever asked about the value of your HSA (you won't be once you change your entries), you should enter a dollar value of the total investment. This number is used to calculate your penalty for carrying over an excess contribution (which you won't be doing), which is the smaller of 6% of the smaller of line 48 (the excess carried over) or the value of your HSAs on December 31, 2025 (including 2025 contributions made in 2026). So you can see that just reporting the cash in the account would artificially reduce the penalty - see line 49 on form 5329.

This is really disappointing.  It seems like the IRS is double-penalizing you right at the crossover from year 1-2.  From then on, it's a full calendar year, but in the beginning they are pretty much going straight from 0% to 12% (if you account for extensions on the original year).  This is truly bizarre.

What kind of income?   All income gets entered in the Income section.    The categories are listed below.    If you need specific instructions, let us know what kind of income you have.      Wages and Salaries Form W-2 Self-Employment Schedule C, 1099-NEC, 1099-K, expenses Unemployment Government benefits on Form 1099-G Other Common Income Tax refunds, 1099-G, 1099-NEC, 1099-MISC, 1099-K Investments and Savings 1099-B, 1099-INT, 1099-DIV, 1099-DA, digital asset Less Common Investments and Savings 1099-OID, contracts and straddles, etc. Retirement Plans and Social Security 1099-R, IRAs, 401(k), early withdrawals Rentals, Royalties, and Farm Income and expenses from rentals, patents, oil/mineral rights, and farm Other Business Situations Self-employed retirement and health insurances, losses, etc. S-corps, Partnerships, and Trusts Income from partnerships, S-corps, LLCs and REMICs Less Common Income Home sale, canceled debt (1099-C, 1099-A), 1099-SA, gambling, etc.

Yes, you should delete the rental property since it was not rented or put on the market as such. It would likely be considered an investment property as opposed to a second home, however, since you didn't have any personal use of it. A such, when you report it's sale, you can choose the Land (other investment purpose) option for the type of property sold. That will allow you to deduct a loss if applicable on the property.    You enter investment sales in the Wages and Income section of TurboTax, then Investment Income, then Stocks, cryptocurrency, Mutual Funds, Bonds, etc... Skip the section where it asks if you want to upload your tax documents. Choose Other as the type of investment sold.

Looking at your entries, it appears you may have only entered a number in one of the boxes on the screen that asks when you made the retirement contribution.  To fix this go back through the IRA entries and when you get to the screen asking if you made any contributions in January through April, enter $8,000 in both boxes not just the Jan- April box.  The first box is asking you what total contributions have been made for 2025, the second box is just about the timing if other than during 2025.   Also, the question about not covered by a plan at work does pop up for me on MAC and PC.  For the online version, it MAY be missing due to the lack of W-2's so TurboTax is assuming you are NOT covered by a plan at work since you have not entered any W-2's which would be the indicator that you could be covered by a plan at work.  But the fact that the box is blank on the form itself, says this is not causing any part of the issue.    @craig43