Entering a 1099-B for stocks is dead simple, you enter in a few numbers (cumulative buys, sells, and wash sales) and you’re done. You transmit your trade history to the IRS digitally.

It takes me about 20-30 minutes to enter a W2, 1099-INT, 1099-B, 1099-B (futures) and a 1256 (straddles and index options) into FreeTaxUSA every spring.