When Quicken cannot match the shares being sold to a specific prior purchase lot, it asks you to verify a cost basis for each sell transaction one at a time. It would be more efficient to display a list of all transactions that need verification in a single dialog, and allow you to select Average Cost' or 'Lot Identification' (and specify Lots) within that dialog, then save them all at once.
Instead of this many times…
Allow something like this (one time)..