Step 5. Stock: Tax return (April 3, 2018.) Questions or comments to: email@example.com
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Member advice on stock issues for US tax return
Extension of time to file. "April 17 is the deadline for most taxpayers to file an extension and to pay taxes owed to avoid penalty and interest charges. If you file for an extension, your return is due October 15, 2018. ...an extension of time to file your return does not grant you any extension of time to pay your taxes." IRS link (You can file for an extension with a paper form or using TurboTax.)
If an entry on your tax return doesn't match what a broker, administrator, or transfer agent reported to the IRS as shown in your 1099-B, you can enter the correct data and include an explanatory note in your return -- using your tax-preparation software or via your tax preparer. Eventually, the IRS will mail you a computer-generated notice about the discrepancy between your tax return and the broker reports. You then follow the instructions in the notice to reply with a copy of your supporting data. If you have already filed before discovering this issue, you can file an amended return via your tax software or preparer.
You can do all of this with tax-preparation software -- including downloading the 1099-B information from your broker's website. (See TurboTax Import Partner list.)
TurboTax: Using TurboTax for ESPP shares -- step-by-step with screenshots. Now v02 with Capital Gain Worksheet and Form 8949.
New: If you do not have employee purchase records -- or did not input your lot-and-cost information into your broker's system -- for a particular time period before 3/1/2002, you can use the current version of the HPAA spreadsheet to help estimate the average cost basis for the various spinoff shares over that period. (Note that current spreadsheet is dated April 7 -- version 14 since 2004.) Go back to Step 4: HPAA Stock Spreadsheets
When you don't know dates, enter a single lot with "various" as the date. Brokers do that on their 1099-B reports to the IRS -- and TurboTax will let you enter "various."
Be sure to save the documents you used -- including a copy of the HPE "Dear Shareholder" letter.
Be sure to save the spreadsheets you have modified -- under a different filename -- and keep them for future reference when you sell shares, etc.
If you elect to hire professional help, the IRS explains the different types of tax professional. You can search the online IRS Federal Tax Return Preparer Directory by geography and qualifications -- or by name to verify credentials: Directory of Federal Tax Return Preparers.
HP Share Ownership Program Tax Reporting provides helpful information collected by HPAA member Alan Silverstein and posted on his personal website: (Revised December 11, 2013.)
Official IRS website, which is well done and has a very good search box: https://www.irs.gov
Official TurboTax help site: https://ttlc.intuit.com -- which you can search even if you don't use TurboTax or don't want to register your copy.
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For more mutual help on this topic and many others, join the independent HP Alumni Association. If you were formerly a regular, direct employee of Hewlett-Packard, HP Inc, or Hewlett Packard Enterprise -- or have a defined retirement or termination date, join the HPAA. No charge, thanks to HPAA members.
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