Now that it's tax season let's get filing. If you're a TurboTax user, then please follow the instructions below to learn how to import your tastyworks data to prepare your taxes. Before you get started, make sure that your software is up-to-date. Typically, TurboTax will check for updates each time you launch the software, as illustrated below:



*Please Note: Importing tastyworks data requires TurboTax Premier or better. Also, there are transaction limits when importing your transaction data (Form 8949 & Schedule D) with Turbotax Online and TurboTax CD/downloadable software. TurboTax Online has a 500 transaction limit. TurboTax CD/downloadable software has a ≈ 2,000 transaction limit per brokerage account. If you experience any issues with importing data using the Online version then may want to consider switching to the CD/downloadable software. To read more about this limitation, please click here.


Sections



Importing Securities Data
Start by going to the Federal Taxes tab, then click Wages & Income. Once in the 2018 Income Summary section, scroll down and select the Investment Income section and select the Start button for Stocks, Mutual Funds, Bonds, Other.


After clicking Start, the software will ask Did you sell any investments in 2018. If you closed a position in a non-IRA account and received a 1099-B, then click Yes.


The software will ask if you received a 1099-B. If you did, then please click Yes.


Now, TurboTax will ask How do you want to enter your Form 1099-B into your return. Select Import from my bank or brokerage.


Next, search for tastyworks in the search field, then select. After selecting, click Continue.


After selecting tastyworks, enter your tastyworks account number (for example, 5UT12345) and social security number/TIN (without dashes). Then click Continue. To locate your account number, please log in to your account at tastyworks.com or click here. Your account number is listed in the blue Account Status area. 


The password for entity accounts is the Tax Identification Number (TIN) associated with the account. Additionally, for a joint account, the password is the SSN of the person who initially started the joint account application.


*Please Note: If you just installed your software and are experiencing issues with logging into your tastyworks account, then your software may need an update. Simply close TurboTax and relaunch it. Your TurboTax Software will retrieve updates as necessary, and you should be able to log in after that.



When you enter your tastyworks account credentials, the software will retrieve your information. This may take a moment.


When the software retrieves your information, you'll reach the These Documents are ready for Import area. Please select your account then click Import Now. If your Consolidated 1099 included a Form 1099-DIV, Form 1099-INT, Form 1099-OID, or Form 1099-MISC then they will also list in this area.


After clicking Import Now, the software will ask: Tell us if any of these apply to your sales. If you're ready to go move on, then click the last radio button labeled None of these apply to me. Then click Next.



Your transaction data is displayed in this area. The length of the list will depend on how many transactions you have performed. To continue, scroll down and select Done.



Did you receive an error that some of your positions requires some extra info?


If you receive an error stating that a transaction has missing information or requires information, then chances are you held a position to expiration. To remedy this, please check your 1099 to make sure that the missing data is, indeed, an expired position. 


You can quickly locate expired transactions in your Form 8949 by looking for EXPIRATION spelled out in the Additional Information column. Below, we have an example of a 2-lot of TSLA 01/19/18 285 puts that expired worthless.


If the position did expire and you see YES displayed in the Needs Info Column, then click the Edit button. Below are the two TSLA 285 puts that expired worthless.


When editing, enter 0.00 into the cost basis for expired short positions or enter 0.00 into the proceeds for expired long positions. In the example below, since these puts were short and expired worthless, then you'll need to enter 0.00 into the cost basis. Click Done when complete and you'll return back to your transactions.


After viewing your transaction data and clicking done your short-term, long-term, and unknown-term numbers should align with what is displayed in your Form 1099-B Totals Summary page in your Consolidated 1099. When complete, click Done. In the example below, the short-term gain in TurboTax matches the short-term on the Totals Summary Page. TurboTax will round to a whole dollar amount.


After clicking Done on the prior page, TurboTax will ask: Do you have any other investment sales from another bank or brokerage? If you do then click Yes, otherwise click No. If you click No, then you will return back to the Federal Taxes > Wages & Income section.



How to file when you have more 2,000 transaction

Did you receive a, Your request exceeds the maximum tax records allowed by Turbo Tax error? Well, no need to fear! You can still use TurboTax, but you'll have a few extra steps. You can also read more about this extra step by visiting the TurboTax FAQ, or click here.



After receiving the error message above, click OK. Then, click Back twice to return back to the Let Us Enter Your Investment Sale Info. Because of the limitation in TurboTax, you'll need to select I'll type it in myself then click Continue, as illustrated below.


Next, TurboTax will ask Which bank or brokerage sent you this form? (your Consolidated 1099). Select My bank/brokerage isn't here in the dropdown menu. Then type tastyworks in the Name of bank or brokerage and enter your tastyworks account number.


After entering your brokerage information, this is where you'll need to refer to the Form 1099-B Totals Summary of your Consolidated 1099-B to view your total Proceeds and Cost Basis. In the example below, you'll want to select I'll select a summary for each sales category (red box). Then enter the total Proceeds (orange box and arrow) and Cost Basis (blue box and arrow) into their corresponding box and select the Sale Category from the dropdown menu. The box letter will corresponding with sale category (green box).


If your account was subject to any Wash Sales, then you'll need to click I need to enter amounts from box 1f, box 1g, or other adjustments. The IRS Code for Wash sales is W, which you can find on page 9 of the Form 8949 instructions from the IRS. After entering, click Done.


After entering your Proceeds and Cost Basis and Wash Sales (if applicable) the software will ask Do you have another sale to enter from your tastyworks 1099-B? If you had any profit/loss from positions subject to Long-Term or Unknown Term then click YES. Otherwise, click No.


Here, the software will sum up your total profit or loss. You'll notice that the Gain or Loss will match what is on your Totals Summary of your 1099-B, as illustrated below.


In some cases, TurboTax will prompt you to mail your Consolidated 1099. If your filing requires you to mail your 1099, then instructions will follow about where you need to mail your tax forms to.



Section 1256 Contracts: Cash-settled Index Options & Futures

Before you pat yourself on the back and relax, you may want to check and see if you traded any cash-settled index options or futures (Section 1256 Contracts). In other words, if you see a Regulated Futures Contracts section in the 1099-B Totals Summary or received a Substitute 1099-B from trading futures, then you need to this to continue. If this applies to you, then you have one more step.


If you did not trade any Section 1256 Contracts, then you may disregard the section below. To read more about Section 1256 Contracts, then please click here.


Now, it’s time to enter the profit/loss from Section 1256 Contracts. Return to the Investment Income section. You can enter your profit/loss by clicking the Start button next to Contracts and Straddles.


You’ll be greeted by this section. Click Yes to proceed.


Next, check any elections that are applicable to you. Otherwise, click Continue to move on. Of course, we always suggest consulting a tax professional if you have questions about whether an election applies to you. 




We’re almost there, now check Section 1256 contracts marked to market.


Now you should be at How to Report Your Transactions page. Select I’ll report the totals from each broker or account.


Before you move on to the next section of TurboTax, you will want to dig up your Consolidated 1099. Namely, you'll want to go to the Form 1099-B Totals Summary page where you can locate the Aggregate profit or (loss) on contracts from trading Section 1256 Contracts. Below, we’ve illustrated where you can find this.


**ATTENTION FUTURES TRADERS: If you traded any futures contracts as well as any Section 1256 options, such as a cash-settled index option, then you will need to take the sum of the profit or loss in your Consolidated 1099 (pictured above) AS WELL AS the total profit or loss from Form 1099-B Futures (pictured below). Both forms can be found in the Tax Center. An example of a Form 1099-B Futures with a $542.30 profit is illustrated below:



In this example, the Consolidated 1099 booked a $74.68 profit. You’re now ready to enter this number into the “Section 1256 Contracts” section of TurboTax. Here, you will need to enter:

  • Brokers: tastyworks
  • Account Description: You can write whatever you want in here, as it's solely used as a reference.
  • (Loss): if there was a loss then enter the amount here
  • Gain: $74.68 (or $542.30 + $74.68, which is $616.98, if you traded futures as well)


Now you’re ready to enter the net effect of all your trading of Section 1256 Contracts. You will either have a number in (Loss) or Gain, and not in both. After entering, click Continue.


Lastly, you may notice that TurboTax will round to nearest dollar, which in this case is $617 (Index options + futures trading). If everything looks correct, then click ‘DONE.’ You will return to the Your 2018 Income Summary page.



Take a deep breath, you’re all set! Now, go ahead and pat yourself on the back.