Filing an extension is super easy. By filing an extension, the IRS will give you an extra six months to file your tax return without penalty. The deadline to file your 2013 tax return is April 15th, 2014. With an extension, your deadline to file a tax return will be October 15, 2014. However, an extension of time to file is not an extension of time to pay. If you owe, paying the IRS by the April 15th deadline results in avoiding any tax penalties and interest.
Speed: 1 minute. Cost: 49 cents (for postage). You can file an extension quickly and painlessly by using Form 4868. Print the form, fill in your name and SSN, and mail it to the IRS. That's it. Here's links to Form 4868 (pdf) and the mailing addresses.
Do you need to fill out Lines 4 to 6 of Form 4868? This is where you report your estimated tax liability, payments made, and an estimate of your balance due. If you don't have an estimate of your tax bill, just leave those fields blank. On line 7 indicate the amount you are paying, or put zero if you aren't sending in a payment. Be sure to mail this before the post office closes on April 15th. If the post office has already closed, use one of the online services (below).
Speed: about 5 minutes not including the payment section. Cost: $34.95 for personal tax extensions; $39.95 for business tax extensions. FileLater provides a estimate of federal tax based on inputting an amount for wages and other income and assuming that the taxpayer is taking the standard deduction. Users can schedule a direct withdrawal from a bank account to remit extension payments. FileLater also supports the filing of extensions for business tax returns for corporations, partnerships, estates and trusts. FileLater provides users with the option to sign in using Facebook in lieu of creating a new account.
Speed: about 8 minutes. Cost: free. Start by clicking on the "File Online Now" button from H&R Block's extension page. The H&R Block software requires that the user input an estimate of his or her federal tax liability and the total of tax payments that have been made for the year. H&R Block provides a separate utility for estimating what the federal tax liability might be via a pop-up window. That pop-up window didn't let me scroll down even though I could see that some of the text and input screens were located below the screen. H&R Block did not provide an option to remit payment of tax via bank account or credit card. Accordingly, any payments will have to be made separately.
Speed: about 12 minutes not including the payment section of the process. Cost: free. Click "File Extension" and then on the following page click "File Extension Only." After creating your account, eSmart Tax gathers information necessary to file your extension, but does not provide an estimating utility like those found in TurboTax, H&R Block At Home, and FileLater. Users can set up a direct payment from a bank account to remit any tax.
Speed: approximately 15 minutes. Cost: free. Free File Fillable Forms is a free tax filing service sponsored by the IRS and hosted by Intuit, the makers of Turbo Tax. After creating your account, start with one of the tax forms such as 1040EZ, 1040A or 1040. Fill out your name, address and SSN. Free File Fillable Forms has a calculated field for the balance due (line 6) of Form 4868, which requires that users have a calculated tax liability, payments, and refund or balance due calculation on the main tax form. Thus, users will need to fill out at least some information on the main tax form to generate these figures. After filing out that basic information on the main tax form, click the "File an Extension" icon in the upper right-hand portion of the screen just under the logout link. That will open a screen that looks similar to the paper Form 4868. Fill out the rest of the data fields that are below the Form 4868. Lines 4 and 5 (estimate of total tax liability and total 2012 payments) can be different amount than those calculated on the main tax form. Once those two lines are filled out, click on the "Do the Math" button located at the bottom of the screen, and Free File Fillable Forms will calculate the balance due amount for line 6. Fill out the amount being paid with the extension on Line 7. Be sure to fill out the rest of the data fields by scrolling through the rest of the screen. These data fields include email address, disclosure statement, prior year PIN fields, current year PIN, and date of birth. Also in those data fields, users can set up a payment from a bank account. Work in progress can be saved by clicking the "Save" icon in the upper-right hand corner of the screen. Once all the required data fields have been filled in, the "E-file Extension Now" button in the mid-upper-right-hand side of the screen will become enabled (instead of being greyed-out). Click on that button to e-file the extension. Definitely not user-friendly.