I have wasted a lot of time on this WHFIT experience as well. The security I bought does have a 17 page tax document that fails to provide any insight as to how to report this on our taxes. Like yo...
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I have wasted a lot of time on this WHFIT experience as well. The security I bought does have a 17 page tax document that fails to provide any insight as to how to report this on our taxes. Like you, I had Short Term Gains (Non-Covered) for 2025 - one for each month, to be exact - although not a single one of these allegedly short term sales appeared in any of my monthly statements from my brokerage firm. Later on in my 1099-B, I had the WHFIT listed again, and the same amount of Short Term Gains was now listed as an "Investment Expense." I called my brokerage, and received no help. I called the company (whose WHFIT is in my holdings) - same result. I searched online too, but you've probably already guessed by now that they were of no help either. My main question is this: What is the point of calculating an adjusted cost basis if I have sold nothing? I bought 250 shares in late 2024. I still hold 250 shares in April of 2026, despite allegedly making 12 short term sales in 2025. I have small monthly gains that are reported to the IRS, but how does one report an adjusted cost basis for something they didn't sell? Nobody can answer that. I did not sell a single share. I did not sell even a fraction of a share. Like you, when I filed my taxes, I listed each tiny monthly gain as a short term sale because that is what my brokerage provided to the IRS on my 1099-B. For my cost, I listed $0 and reported that my cost basis was missing. On that next page, I reported an investment expense charge equaling each tiny gain. I did that for each monthly gain. Who knows if this is how it is supposed to be done or not - I can find no one who can tell me how to handle this - even my wife, who is an accountant. All I know is that I was charged the exact amount of the proceeds I allegedly received. Therefore, the way my rudimentary brain calculates things, I calculate that I gained absolutely nothing. I came out neither ahead of behind - hence the gain/loss of $0. Of course, I have calculated the difference in my cost basis for this stock, which I wish I had never bought in the first place, but I will need to know that number when I eventually sell this pig off for a loss. Until then, that number seems to be irrelevant. By all means, if someone has a better solution, please share it with all of us. That will save a lot of headaches for everyone else who holds one of these WHFITs. And TurboTax, it would be swell if you engineered a question into the Step-by-step system that asks if the security is a WHFIT. That would be wonderful, provided that you provide a slick way of dealing with these things.