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For all taxpayers in the US, the deadline for filing tax returns with the IRS for the tax year 2009 is April 15, 2010. In any tax year, stock compensation income, such as from an NQSO exercise, an ISO or ESPP disqualifying disposition, or the vesting of restricted stock, can raise your income tax and make your return complex. For help, see a special section of this website called Reporting Company Stock Sales.
Postponements are available for US military personnel who are serving in combat zones, including Iraq and Afghanistan. The filing deadline for military postponements is usually put back by 180 days from the time the taxpayer leaves the combat zone.
To gain an automatic six-month extension for the due date of your tax return (until mid-October), you can use IRS Form 4868, Application For Automatic Extension Of Time To File. However, the IRS is encouraging taxpayers (or tax preparers) who plan to file extensions to do so electronically through the e-file system. No explanation or signature is needed to get the automatic extension. Treasury Decision 9229 (published on November 7, 2005) simplified the procedure for six-month extensions. Previously, they were available only through a two-step process of extending the deadline by four months and then by an additional two months.
The safe harbor for avoiding a penalty for your extension is paying at least 90% of the total actual income tax. If you owe any taxes with the actual return that you file by the extension deadline, you owe interest on any underpayment going back to the original mid-April due date. The IRS publishes the rates every quarter (see Internal Revenue Code Section 6621). If you need to pay more than 10% of your total tax with your actual return after the deadline, interest and penalties will apply. Alert: To avoid the failure-to-file penalty on what you owe, you must file the extension no later than the original deadline of your return (for details, see IR-2006-58). Because payment of the actual tax is not delayed (just the period for filing the return), you must accurately estimate how much tax you owe. By paying 100% of your tax when you file the extension, you avoid interest and penalties. The penalty for missing the extended deadline is 5% (4.5% for filing late and 0.5% for paying late) of the balance due for each month, or part of a month, up to a maximum of 25%. You can face a failure-to-pay charge of 0.5% a month on any unpaid taxes if you have not paid at least 90% with the extension. The IRS does not assess both penalties for the same period. The 0.5% penalty will also be assessed if you do not pay all of the tax due with the final tax return. If you lack the funds to pay your income tax, you may want to consider asking to pay by installments or working out an offer in compromise with the IRS (see a related FAQ), or even paying by credit card through special service providers (they charge a fee for a percentage of the payment).
Don't forget about your state tax return. For example, if you pay tax to the state of California and cannot file by the due date, you will need to complete and submit Form FTB 3519 to apply for an extension. As with your federal return, you will still need to pay at least 90% of any tax you owe by the original filing deadline.
If you expect additional income from stock grants, and if your salary withholding and the withholding at the statutory rate for supplemental income (25%; 35% for amounts over an aggregate of $1 million) will be inadequate to cover the taxes you will owe for the full year, consider making estimated tax payments (or see if you can adjust your salary withholding). To avoid any penalties on your tax return next year, be sure that over the upcoming year you pay the IRS either 90% of your expected tax bill or 100% of this year's taxes (for adjusted gross incomes over $150,000, it is 110%). The penalties are calculated on a quarterly basis, so you need to make estimated tax payments in the quarter that you have earned the income. If you are basing your estimated tax payments on your prior year's tax, then the estimated payments should be spread equally over the four quarters to avoid penalties.
The details of estimated taxes, including the due dates, are discussed in IRS Form 1040-ES and, elsewhere on this website, in the sections NQSOs, ISOs, Restricted Stock, and SARs. |
