I have more than 5000 transactions

TurboTax Desktop will only handle about 2000 stock transactions. Instead, you can enter summary totals.  If any of your summary totals are greater than $10 million, you will have to use a work around.  You will have to split that summary into more than one transaction.  For instance, if your Short Term Non-Covered transactions total $12,000,000 you will need to split it in to three summaries of $4,000,000 each.

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 your return (if it's not already open) and search inside TurboTax for the phrase stock sales.
2. Select the Jump to link in the search results.
3. Answer Yes to both Did you sell any investments? and Did you get a 1099-B?
   • If you land on Here's the investment sales info we have so far, select Add More Sales. Then answer Yes to Did you get a 1099-B?
4. When asked how you want to enter your 1099-B, select I'll type it in myself.
5. Select or enter your brokerage on the next screen and continue.
6. On the following screen (Tell us about...) select the second option, I'll enter a summary.
7. On the same screen, 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 Done.
8. Follow the onscreen instructions to enter additional sales or to view a summary.

Yes, you would mail your documents.  However, this process is not difficult and you can do separate sales as long as long term and short term are not comingled (must be separated).

• Long term is a holding period of more than one year and receives capital gain tax treatment (0%, 10%, 15%, 20% depending on your regular rate of tax)
• Short term is a holding period of one year or less and receives ordinary gain tax treatment (your regular rate)

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).

If you still feel that you need additional assistance you can use a Live expert click this link for more information.

 "Live Tax Advice"