A simple fix to this is (and this is something that is encountered using even the most "sophisticated" of tax software systems), If you are able to extract your year end statement and it provides you with totals of S/T vs. L/T transactions (you might even have 4 different categories on your statement - depending on if basis was/was not reported to the IRS, so be sure to not miss any sections of the statement), you should separate them out yourself on a spreadsheet, tally up the information for each category of transaction, and enter as such. This is, making sure, of course, that the firm you use is providing you with cost basis and sales price as well as #shs per transaction.
You can also extract to Excel, but that takes more work than step one. What the IRS is looking for is the following:
1. Net S/T Capital Gains/<Losses> , based on purchase date, cost basis, sale date, and proceeds
2. Net L/T Capital Gains/<losses>, based on purchase date, cost basis, sale date, and proceeds
In short, each section of your statement that has a total that states "Has Been Reported to the IRS", will be treated as one transaction for taxability purposes. So, if you have 1, 2, 3, or 4 of these totals lines, then that would be the corresponding number of transactions you will have. Make sure that you do not include any section that starts with "Transactions NOT Reported to the IRS" as these are categorized already by your brokerage firm for you as non-reportable pieces of information.
ALSO, make sure you do not miss any dividend and interest income, Foreign Income Taxes Paid, etc., if your statement is all you rely on to report your information to the IRS.
