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How Can I Enter Form 1099-B - Aggregating Multiple Stock Transactions in ProWeb? 

Form 1099-B is used by Brokerage firms to report stock transactions. Brokerage information may have many transactions that can be aggregated on the tax return instead of being entered one by one. 

Transactions can be aggregated when they fulfil the following criteria: 

  • Form 1099-B Boxes 1f and 1g are empty
  • Form 1099-B Box 2 "Ordinary" checkbox is not marked 
  • Form 1099-B Box 3 "QOF" checkbox is not marked 
  • Form 1099-B Box 12 indicates basis reported to the IRS
  • The taxpayer forfeits to elect to defer income due to a QOF investment, nor terminating a QOF investment deferral
  • No more adjustments are required to the basis or the gain or loss
  • There is no change to the gain or loss. 

You will be required to individually enter transactions that cannot be aggregated. If any aggregated entry is made, a PDF copy of the brokerage statement(s) must be attached to the tax return. 

Pro Tip: To keep the size of a large brokerage statement low when scanning it to a PDF for the purpose of e-filing, scan it in black and white then use a resolution of not more than 300 dpi. 

To aggregate transactions in PoWeb: 

  • Go to the Federal Section of a tax return 
  • Proceed to the Income Section 
  • Then to the Capital Gains and Losses section 
  • Select Capital Gain and Loss Items 
  • Click +Add a Capital Gains Transaction - For MFJ returns, show the owner of the return. 
  • Description of Property - Enter a description for instance, 1099-B ST (for short-term) 
  • Date Acquired - Click Alternate Option then choose either Various - Short Term or Various - Long Term as may be appropriate
  • Date Sold - Enter the tax year’s last day 
  • Sales Price - Enter the aggregate sales price 
    • Select cost basis type - Select 1099-B, Box 12 Cost Basis Reported to the IRS 
  • Cost - Enter the aggregate cost basis 
  • Adjustments - Mark the box next to M - Reporting Multiple Transactions on a Single Row. 

Once done with the transaction, click Save & Enter Another in case you want to enter another transaction. If that is not the case, click Continue. 

To attach a PDF of the documents that are showing the information of the aggregated transactions: 

  • Go to the Federal Section of a tax return 
  • Proceed to the Income Section 
  • Then to the Capital Gains and Losses section 
  • Select PDF Attachments - You can either upload the PDF or drag and drop it into the upload area
  • Attachment List - click on this when you are done with attachment of the files. 

Additional Information:

IRS: Instructions for Schedule D

IRS: Instructions for Form 8949

IRS: Publication 550

IRS: Instructions for Form 1099-B Proceeds From Broker and Barter Exchange Transactions