sure they will. I have used different brokers and if I sold a security at a loss and then repurchased it during the wash sale period, that sale will be reported on the 1099-B as a wash sale. if I then sold the replacement shares before year-end and do not repurchase them during the wash sale period, the deferred loss will now be allowed but it will be reflected in the second sale. at least that's the way my brokers have reported them. there is a good reason. the holding period of the original shares in the wash sale tack on to the replacement shares so what could have been a short-term transaction could end up as a long-term transaction.
