Retirement tax questions

Not an issue.  Follow the steps below and TurboTax will handle your transactions.  You can still e-file using the instructions below making sure to group short term and long term entries separately.  Likewise, if there are any wash sales they must be entered individually if the wash sale rules apply in your situation.  I tested an entry with a hundred million transaction and it worked easily in TurboTax.

The steps to enter a summary of your sales transactions is provided below. 

1. Open or continue your return (if it's not already open) and search (upper right) for the phrase stock sales > Press enter
2. Select the Jump to link in the search results.
3. Answer Yes to both Did you sell stocks, mutual funds, bonds, or other investments? and Did or will you receive a 1099-B form or brokerage statement for these sales?
4. If you land on Here are all your 1099-B sales, select Add sales from a different brokerage. Then answer Yes to Did or will you receive a 1099-B form or brokerage statement for these sales?
5. When asked how you want to enter your 1099-B, select I'll type it in myself.
6. Select or enter your brokerage on the next screen and continue.
7. On the following screen (Tell us about...), answer the questions until you reach the next screen. Select the second option, Let's enter a summary instead, and select Continue.
8. You'll now be able to enter the total proceeds (sales) and cost basis, along with the sales category (Long or Short term). Refer to your 1099-B for the amounts and category. When finished, select Continue.
9. When you are done, you'll eventually come to the Here's a summary of your broker sales screen where you can edit, delete, or enter more sales.

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 need a blank Form 8453, you can download this pdf, enter your address information and check the box for Form 8949 (this form is really just a cover sheet)

[Edited: 01/14/2022 | 6:06a PST]