Addendum:
You didn't say what kind of 1099, so I answered generically above. If it happens to be a 1099-B with a lot of investment transactions, instead of entering all the individual sales, the program does have an optional method where one can choose to enter a summary and then mail a sales statement showing the transactions to the IRS. But without more info, it doesn't sound like that is what you are asking. Plus you appear to be using Free Edition, which doesn't allow for 1099-B anyway.
