Now that tax season is here, let's put your computer to work. If an H&R Block Tax Software user, then you can import your tastyworks transaction data to prepare your taxes. Please follow the illustrated instructions below, but before you get started, make sure that your software is up-to-date. Typically, the software will check for updates on startup, but you can also update it manually, as illustrated below. 


*Please Note: Importing tastyworks data requires the Deluxe version of H&R Block or better. However, H&R Block Online requires Premium or better. Also, there may be transaction limits with H&R Block Tax Software software. H&R Block Tax Software users with 2,000 or more transactions or H&R Block Online user with 500 or more transactions may experience issues when importing your transaction data (Form 8949 & Schedule D) due to software limitations.


Sections



Importing Securities Data

Once your H&R Block Tax Software has fired up, proceed to the Federal tab and click Income. Afterward, the software will ask Where do you want to go? You’ll see a list of income sources — select Sale of Stocks, Bonds, Mutual Funds, and Other Securities (1099-B) and click Go To.



After clicking Go To, click the Import 1099-B button. After clicking, a window will pop-up and the software will connect to the internet to retrieve brokerage information.



Next, the software will retrieve a list of financial institutions. Please search for tastyworks, then click to highlight and click Import. The software will retrieve login information.




After selecting tastyworks, enter your tastyworks account number (for example, 5UT12345) and social security number/TIN (without dashes). Then, click Continue. Please remember to only enter a non-ira, or non-qualified, account in to the account number field. IRA accounts do not receive a 1099-B. 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.



After entering your tastyworks account credentials and Tax ID, the software will begin importing your data. The amount of time it will take to import is dependent upon the number of trades you made during 2018.


After your import is complete, you will have a chance to review all your transactions. 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. Please review before clicking close on the bottom right-hand corner.


After reviewing and clicking Close, you can complete this step by clicking “FINISHED” on the bottom right-hand corner of the software. You will be prompted one more time to verify your information.


Did you receive an error that some of your positions are missing information?

If you received an error when filing 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, as illustrated below. 


If the position did expire, then you'll need to enter 0.00 into the cost basis for expired short positions or enter 0.00 into the proceeds for expired long positions.




How to file when you have more than 2,000 transactions

Did you receive the following error message below when importing your 1099 transactions? If so, then you had over 2,000 transactions in your Form 8949, which is the limit for H&R Block's Tax Software. No need to panic though, you can still file manually. After receiving the error below, click Cancel.


Next, instead of clicking Import 1099-B you will click Enter Manually.


Now, enter tastyworks into the description. If you are subject to FATCA filing requirements then you can check the box. Otherwise, you can leave it blank. Then, enter your account number.


You can check whether or not you are subject to FATCA filing by referring to the first page of your Form 8949 of your Consolidated 1099, which is typically the next page after your 1099-B Totals Summary Page. You will see a box labeled FATCA Filing Requirement in the middle of the page. If checked, then you must check the FATCA box. 


Now, click Add Sale.


After clicking Add Sale, the software will ask if you want to enter a group of sales. Click Yes. By entering it as a group, all you will be reporting are the totals in the 1099-B Summary Totals Page.


Now, the description of sales. In the example below, since we are reporting short-term sales, then you may enter tastyworks short-term in the Description and VAR-S in the Date Acquired box. 


However, if you are reporting long-term sales as well then repeat these steps from the beginning after submitting. Then you may enter tastyworks long-term and VAR-L into the Date Acquired box. 


Then, enter the Proceeds (red box and arrow) and Cost Basis (blue box and arrow) listed on your 1099 into the software. Lastly, if you are subject to Federal Income tax withholding then enter it. Once complete, click Next.


After entering your group sales information, you'll return to the Tell us about the sales on this Form 1099-B section. You'll notice that the realized gain or loss will match to the nearest whole dollar. Remember, if you need to report long-term gains or losses then repeat these steps. 


Lastly, if you traded any Section 1256 products (typically cash-settled options) and see a Regulated Futures Contract category on your 1099-B Summary Totals Page, then proceed to the next section below.



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.


Now, it’s time to enter the profit/loss from Section 1256 Contracts. Return to the Income section of the Federal tab. Locate and click Go To for Section 1256 Contracts and Straddles


After clicking Go To for Section 1245 Contracts and Straddles, the software will ask, "Did you or your spouse hold any section 1256 contracts or straddles during 2018 that were not sold on or before December 31, 2018?" Please click Yes to access Form 6781 so you can report your overall profit or loss.


Here, you can access Form 6781 to enter your profit or loss from Section 1256 contracts. Click “Whole Form” to enter your total profit or loss from trading these contracts.


Before you venture on to the whole form, you will want to dig up your Consolidated 1099. Namely, page 3 where you can view your profit/loss 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 SPX, 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:


First, you’ll need to check the applicable box. If you’re only reporting trades of 1256 Contracts, then you can check box ‘D.’


In this example, this Consolidated 1099 booked a $74.68 profit. You’re now ready to enter this number into Part I Section 1256 Contracts Marked to Market on Form 6781. Here, you will need to enter:

  • (a) Identification of account: tastyworks (or however you want to label it) 
  • (b) Loss: (if there was a loss then enter the amount here)
  • (c) Gain: $74.68 (or $542.30 + $74.68 if you traded futures)


After you have entered your profit or loss from Section 1256 Contracts, you may move onto the next page to complete your tax filing.