I can't help if the 1099 download isn't working properly; however, there is an alternative if your 1099-B won't import correctly. You can enter category totals instead of individual transactions. To do so in TurboTax Online:
After entering all your sales section totals, Look for "Now we'll help you upload your 1099-B since the IRS requires a copy" and follow the instructions, or you can mail a paper copy of your 1099-B to the IRS. If you want to mail, click on "How do I mail my statement".
Take a moment to double-check that your statements are complete. For each sale listed, there should be:
In some uncommon cases, there will be an adjustment code and adjustment amount.
NOTE: Any sales summaries that include only Box A or Box D sales, and which have no adjustments to gain/loss, do not need to be included on a statement mailed to the IRS.
Here's how to mail your statements:
If you are e-filing your tax return, then mail your statements along with Form 8453 to:
Internal Revenue Service
Attn: Shipping and Receiving, 0254
Receipt and Control Branch
Austin, TX 73344-0254
If you are not e-filing, then mail your statements with your entire tax return to your local IRS office.
Never resolved. Spent a long time on phone with Turbo Tax who really had no idea how to resolve and contacted Morgan Stanley who also could not figure out. I ended up using the alternative method of submitting subtotals from the 1099B form and having to mail the hard copy detail to the IRS. The only tricky part was if you have any wash sales, those are excluded and get a special code in that section.