If information, such as cost basis, is not reported on your 1099-B, you will have to manually enter it in. There is no way to upload your supplement statement into TurboTax and update each individual share. The only workaround for this is to report your totals by group (long term, short term). If you do it this way, there may be be less data entry, but you will have to mail a paper copy of your return and the backup to the IRS.