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Let's clarify your situation.   Line 8f on Schedule 1 (1040) is the sum of HSA distributions that were NOT for eligible medical expenses (line 16 (8889)) plus any taxes due from failure to maintain HDHP coverage (line 20 (8889)).   Did you receive a 1099-SA for taking distributions from your HSA? If so, when you entered it, did you indicate that the whole amount was for qualified medical expenses? NOTE: Whether or not the distribution is taxed is totally independent of your HDHP coverage.   Can you see your form 8889? Is there anything on line 20? If so, you may be taxed for failure to maintain HDHP coverage (i.e., you used the last-month rule in 2024 to increase your contribution limit, but did not keep HDHP coverage for the entire subsequent year, as required.   In short, I don't believe that what you are seeing is the result of any HDHP coverage not being saved.   So, please answer the following: 1. Did you have a form 1099-SA?  If so, was the entire distribution for qualified medical expenses? 2. How did you answer the question, "What type of High Deductible Health Plan (HDHP) coverage did [name] have on December 1, 2024?"  Did you answer either Self or Family?  And if so, may I confirm that you did not have HDHP in every month of 2025?   To repeat, what kind of health insurance did you have on December 1, 2024? Something other than HDHP? 

No, timely payment of your taxes is the responsibility of the taxpayer.   The underpayment penalty will be assessed if any of these apply: "If you don’t pay enough tax through withholding and estimated tax payments, you may have to pay a penalty." "You also may have to pay a penalty if your estimated tax payments are late, even if you are due a refund when you file your tax return." To avoid the underpayment penalty: The amount you owe is less than $1,000, after subtracting withholding and refundable credits. You paid 90% of the tax that you owed for the current year. You paid 100% of the previous year tax, (110% for higher incomes). If your previous year's adjusted gross income was more than $150,000 you will have to pay in 110% of your previous year's taxes to satisfy the "safe-harbor" requirement. "Typically, underpayment penalties are 5% of the underpaid amount, and they're capped at 25%.  Underpaid taxes also accrue interest at a rate that the IRS sets annually."   To avoid this situation it is recommended that you adjust your W-4 with your employer or pay estimated taxes. Underpayment of Estimated Tax by Individuals Penalty

If you're retired, you will not get a W-2.  You will probably get a 1099-R. If your address is on record, it should be mailed to you. This is available through the My Pay website You can create your own profile My pay Profile         

To access your current or prior year online tax returns sign onto the TurboTax website with the User ID you used to create the account - https://myturbotax.intuit.com/ Scroll down to the bottom of the screen and on the section Your tax returns & documents.  Click on the Year and Click on Download/print return (PDF)   If you used the desktop CD/Download editions installed on your computer, the only copy of your tax data file and any PDF's will be on the computer where the return was created.  TurboTax does not store online any returns completed using the desktop editions. The TurboTax tax data files are stored, by default, in the TurboTax folder within the Documents directory.   Go to this IRS website for free transcripts of a federal tax return - https://www.irs.gov/individuals/get-transcript   For a fee of $30 you can get a complete federal tax return from the IRS by completing Form 4506 - http://www.irs.gov/pub/irs-pdf/f4506.pdf

These CCBG funds are taxable income.   You can report this income as Other Reportable Income.   In TurboTax Online, open your return and follow these steps:   Click on Federal in the left-hand column, then on Wages and Income Navigate to the list of Income categories Locate the Less Common Income section and click on the arrow on the right Click Start next to Miscellaneous Income, 1099-A, 1099-C at the bottom On the next page, click Start next to Other Reportable Income.

@mgweb wrote: Ok. Thank you.  Buying a second tax software would still be way cheaper than the $345/hr or somehow over $1000 an accountant wants..... Exactly, and H&R Block Premium and Business is pretty inexpensive considering it can do estate/trust income tax returns AND your personal income tax return (1040).   Just make sure they actually support MN fiduciary (M2 or whatever it is).