So if I understand correctly:You had a position in a mutual fund made up of about 100 lotsIn February 2016, you sold half the holding (real world)In April the other half in April 2016 (real world)Both those transactions were in Quicken - presumably relying on the default FIFO treatment (correct?)You deleted both Sell shares transaction in order to alter the lot specification for each.When you then attempted to re-enter the February sale of half the holding, the program would not let you specify lots. But of you entered it as a sale of the entire holding, the sale would go through OK.Is that pretty much it?The path you described should have been OK, though you should not have needed to delete and re-enter the sales. You should have been able to Edit each sale and specify lots accordingly. I will add however, that deleting and re-entering should be a more reliable approach. The fact that Quicken balked at the half-lot sale lot specification is odd. My approach to addressing that would be:1) Exit the program and restart -- that can at times clear up something that has not gotten fully addressed by other edits.2) Check for any hidden placeholders. Under Edit / Preferences make sure that the option to show hidden placeholders is checked. If there is such a placeholder, delete it as it would seem to be unnecessary. 3) Make sure both sales were deleted before re-entering the sales and re-enter them oldest first. The idea there is that if a later sale specifies a particular lot for the sale, that particular lot should not be available for specification by the prior sale being entered. If all else fails, you might look into restoring a backup and trying again, or simply trying again.HTH
So if I understand correctly:
If you told Quicken to use "average cost" with this mutual fund then the "Specify Lots" button would be grayed out but "Sell all shares..." would still be available.