Please Note: If you received a notification that your Consolidated 1099 is available, then please be aware that your tax data will not be available in H&R Block until ~72 hours after.


Now that tax season is here, let's put your computer to work. As an H&R Block 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. 


A short note about transaction limits

*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 users 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, 5WT#####) and social security number/TIN (without dashes). Then, click Continue. Please remember only to enter a non-ira, or non-qualified, account into the account number field. IRA accounts do not receive a Consolidated 1099. 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.


If you just installed H&R Block and are experiencing issues with logging into your tastyworks account, then your software may need an update. Close H&R Block and relaunch it. The software will retrieve updates as necessary, and you should be able to log in after that.


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


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, they would 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 software's bottom right-hand corner. You will be prompted one more time to verify your information. 

The total proceeds listed in H&R Block may not match your total proceeds listed on your Consolidated 1099 due to the new 0.00 cost basis methodology adopted for short equity options. Furthermore, H&R Block will round each transaction to the nearest whole dollar. As a result, there may be a variance to the net gain/loss listed on your Consolidated 1099. As long as your overall p/l is consistent, the proceeds listed generally do not affect your filing. 



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

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 the Proceeds from Broker and Barter Exchange Transaction section by searching for an EXPIRATION label listed 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, 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 Proceeds from Broker and Barter Exchange Transaction section, which is the limit for H&R Block. 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 and your tastyworks account number.


Now, click Add Sale.


After clicking Add Sale, the software will ask if you want to enter a group of sales. Click Yes. All you will report when entering it as a group are the totals listed in the Summary of Sale Proceeds on the Tax Summary page.


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


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


Then, enter the Proceeds (red box and arrow) and Cost Basis (blue box and arrow) listed on your Consolidated 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. 



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 figures listed in the Regulated Futures Contracts & Section 1256 Options section in the Tax Reporting Statement (generally listed on page 1 of your Consolidated 1099) or received a Substitute Form 1099 Statement from trading futures, 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 products. 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 1256 Contracts and Straddles, the software will ask, "Did you or your spouse hold any section 1256 contracts or straddles during 20xx that were not sold on or before December 31, 20xx?" 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, you'll want to go to the Tax Reporting Statement page (generally page 1), where you can locate the Aggregate profit or (loss) on contracts from trading Section 1256 Options. Below, we’ve illustrated where you can find this.


Did you trade any outright Smalls or CME futures contracts, options on futures, or any Section 1256 options contract? If so, you will need to take the sum of your aggregate profit or loss in your Consolidated 1099 (pictured above) and the aggregate profit or loss from your Substitute 1099 Statement for futures (shown below). Both tax forms, if issued, can be found in your Tax Center. Below, is 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 $64.68 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: $64.68 (or $542.30 + $64.68 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.