Vanguard 1099B import issue

It sounds like an issue on the Vanguard side.  I suggest you delete the 1099-DIV import and download again.  If you didn't the first time, download from the "Stocks, Mutual Funds, Bonds, Other" section of the program.  If the 1099-B still won't download, you will have to manually enter.  If you have a lot of transaction, don't panic, you don't have to enter each one.  You can enter  category totals:

Your brokerage statements should include a summary of your transactions, grouped by sales category, for example, "Box A short-term covered" or "Box D long-term covered." You'll enter the summary info instead of each individual transaction.

1. Open or continue your return (if it's not already open) and search for stock sales.
2. Select the Jump to link in the search results.
3. Answer Yes to Did you sell stocks, mutual funds, bonds, or other investments in 2020?.
   • If you land on Your investment sales summary, select Add more sales. 
4. On the OK, what type of investments did you sell? screen, select Stocks, Bonds, Mutual Funds, then Continue.
5. When asked how you want to enter your 1099-B, select I'll type it myself.
6. Answer the questions until you can select Enter sales section totals.
7. You'll now be able to enter the total proceeds (sales) and cost basis, along with the sales category. Refer to your 1099-B for the amounts and category. When finished, select Continue.

I had to import a second time to get the 1099B included in the list to imported. Selecting the 1099B after the 2nd import the stock sales data got loaded. Issue resolved now.

I'm glad to hear you were able to successfully download the 1099-B.

I have the Premier CD version of TurboTax (not online). It is trying to connect to Vanguard brokerage but fails. Is this not possible with this PREMIER version?

Yes it is possible with the Premier version; please see this link. Try importing again and let us know what happens @NinjaKen.

Mine also did not properly download.  How do I delete the previous, and try again?

If I remember correctly from back in Feb, to resolve the issue you have to import twice:

1) for the 1099 portion (-DIV, interest etc)

2) for the 1099B portion (stock trades etc)

But how do I get back to this stage, and then import again?  Is it not necessary to delete the original, partial info?