Wash sale rule with dividend reinvestment
I was not able to find any authority for the opinion you suggest. Wash sale rules should, IMHO, apply. According to the regulations, you attribute the newly purchased shares to the oldest sold shares for the purposes of the calculation of the disallowed loss and cost basis. (c) Where the amount of stock or securities acquired within the 61-day period is less than the amount of stock or securities sold or   otherwise disposed of, then the particular shares of stock or   securities the loss from the sale or other disposition of which is not   deductible shall be those with which the stock or securities acquired   are matched in accordance with the following rule: The stock or   securities acquired will be matched in accordance with the order of   their acquisition (beginning with the earliest acquisition) with an   equal number of the shares of stock or securities sold or otherwise   disposed of. You can resort to the claim that you have not, in fact, entered into the contract within 30 days, but when you gave the instructions to reinvest dividends. I don't know if such a claim will hold, but to me it sounds reasonable. This is similar to the rules re short sales (in (g) there). In this case, wash sale rules will not apply (unless you instructed to reinvest dividends within the 30 days prior to the sale). But I'd ask a tax professional if such a claim would hold, talk to a EA/CPA licensed in your state.