My 2017 Form 1099 lists over 5000 stock and option trades and is a total of 388 pages long. Most of my trades have wash sales. The aggregate gross proceeds and cost basis are both over $90 million which exceeds the $10 million TurboTax input limitation. This is too many trades to input manually and exceeds the "around 2000" trades import limitation in TurboTax. I would enter the summary totals only but since I have wash sales, I don't think I can and TurboTax won't let me enter 90,000,000 is gross proceeds. How am I supposed to file my taxes without having to enter over 5000 trades manually into TurboTax? It is OK if I enter all of the trades for a particular stock as a single transaction?... Meaning, if I did 85 trades in stock XYZ, can I enter the total gross proceeds, cost basis, wash sale loss disallowed, etc.. from the 85 trades as a single trade on form 8949? Would I still have to send in my Form 1099-B along with form 8453 if I did it that way? Please help, thank you.
If you cannot import the 1099-B you can report summaries instead of individual transactions. Under Let us enter your investment sale info select I'll type it in myself. Later when you Tell us about your 1099-B, choose I'll enter a summary for each sales category. Click the Learn More and How do I? links for assistance. (Click the screenshot below for reference.)