In Nov of 19, I cashed out all of my stocks shares (2266) in an investment account that I have had for roughly 30 years. I have not contributed to the account for over 20 years, it just kept building up on its own. I received a 1099-B which 851 shares were divided into long and short term investments. The remain 1415 shares were not categorized. For the 1415, the 1099-B states "Transactions for which basis is NOT reported to the IRS and for which short-term or long-term determination is unknown. You must determine short or long term gain\(loss) based on your records and report on Form 8949, Part II, with Box E checked, as appropriate. "
1. How do I go back 30 years to check for gains/losses?
2. Do I really even need to check? Will I get into trouble by the IRS if I don't?
1) If you did not record the basis (understandable, considering that it was 30 years ago), just use the basis your brokerage assigned. If they assigned no basis, then you will have to use a zero basis and recognize the full gain on the sale. Since these investments were held for over one year, they will be long-term.
2) No. You can just take a zero basis. But if you think you can track down the basis, it will likely save you money in tax.
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Sometime around 2012 , the funds became obligated to track your reinvested dividends.
For the holding period before that, it is your responsibility to do that.
See IRS Pub 550 Table 4-1 for an example of the records you are supposed to have been keeping.