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.
- Open or continue your return (if it's not already open) and search for stock sales.
- Select the Jump to link in the search results.
- 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.
- On the OK, what type of investments did you sell? screen, select Stocks, Bonds, Mutual Funds, then Continue.
- When asked how you want to enter your 1099-B, select I'll type it myself.
- Answer the questions until you can select Enter sales section totals.
- 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.
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