As long as you make a payment you've filed for an extension. From the IRS site:   Get an extension when you make a payment You can also get an extension by paying all or part of your estimated income tax due and indicate that the payment is for an extension using Direct Pay, the Electronic Federal Tax Payment System (EFTPS), or a credit or debit card. This way you won’t have to file a separate extension form and you will receive a confirmation number for your records. ... View more

Hi, Critter(-3).   Yes, of course.  I understand.  It's not a system limitation but, rather, a mental management challenge for me.  At one time, I had a bunch (5-7 years) of TurboTax versions installed and it was distracting and confusing.   I have the CDs so maybe I'll find an old year and install it to see how bad my memory is getting.   FWIW, I do have a gripe that TurboTax and TurboTax Business editions both use the same file extension on Windows (e.g., "tax2021").  This means that one cannot double click on a file and have it open the right program.  Rather, one must open the program and point to the right file.  If anyone from TurboTax is following this thread, please fix this. ... View more

Yes. Based on your information, you did use the full cost basis of the stock without yet reporting the liquidating distribution. See the information below about when you must report the amount from box 9.   Liquidating distributions, sometimes called liquidating dividends, are distributions you receive during a partial or complete liquidation of a corporation. These distributions are, at least in part, one form of a return of capital. They may be paid in one or more installments. You will receive Form 1099-DIV from the corporation showing you the amount of the liquidating distribution in box 8 and/or 9. Any liquidating distribution you receive is not taxable to you until you have recovered the basis of your stock. After the basis of your stock has been reduced to zero, you must report the liquidating distribution as a capital gain. Whether you report the gain as a long-term or short-term capital gain depends on how long you have held the stock.   If you are still recovering your cost basis here are the records to keep.   Records to keep: (Required as routine for any dividends and investment purchases) The amounts you paid for this investment from the beginning until all liquidation payments have been received.  This would include any reinvested dividends, if applicable.   Total amount of shares purchased at each purchase date  Total of any prior year (before liquidation) return of capital dividends / nontaxable distributions (shown on Form 1099-DIV) Forms 1099-DIV or all years as proof of any return of capital / nontaxable distributions These records may be needed until three years after the final liquidation is paid out. If and when you receive liquidating distributions that exceed your cost basis only then do you have a reportable tax sale transaction.   If you have recovered your cost basis and now need to report capital gains use the information at this link.  You will have 'sale proceeds' but zero cost basis. The sales proceeds will be any part of the liquidating distribution that is in excess of your original cost basis. Where do I enter a capital gain? ... View more