No, you won't be able to enter a negative cost basis into TurboTax. If the transactions at issue here relate to short puts or covered calls that were closed at a loss, the way to report transactions of this type is to enter your buy to close cost as the purchase price--even though it came later in time than the sell to open transaction. The proceeds you received when effecting the sell to open transaction should be entered as your proceeds. You will also have to reverse the sell to open date and the buy to close date so that the dates appear in chronological order. If the purchase date and the sale date are not in chronological order, you will likely see an error message indicating that the sale date cannot precede the purchase date.
@nirlay
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