If you closed out the position entirely at the end of the 2 days and didn't repurchase that stock again for at least 30 days, you are allowed to take the loss. The way the wash sales work is that the loss from the first one has to be added to the basis of the second, so the loss on line 2 would be zero. You would then add $26 to $337, and the loss would become $39. It works that way all the way down, so you eventually get to the $543 loss. Instead of entering each transaction individually on the 8949, you can enter the total sale and total cost and then enter "M" in the adjustment box to indicate multiple entries. If you have alot of these, you can just enter the totals and then send a copy of your 1099B to the IRS. Read the instructions for Sch D and form 8949. If you can't handle this yourself, take it to a professional.