This is actually two questions. No. 1: Is there a way around having to manually input the cost basis for every security? No. 2: When resolving a placeholder for cost basis information, the program asks you to enter the date of the purchase (or acquisition), the number of shares, the price per share, and the total cost. When I enter the number of shares and price per share, the total cost often does not match the statement. I tried entering the number of shares and the total costs so the program will calculate the per share value on it's own, but the price per share does not match the statement. Which way is correct for accurately computing gain/loss?