Today, January 16, 2009, is the first day that someone can file a return electronically with the IRS. E-file is available to people using tax preparation software on their desktop, using a Web-based application, or going through a tax professional. Today is also the first day that the Free File software is available. Twenty different software companies are offering free access to their tax prep software through the IRS Free File Alliance. I'll best trying out each of these free software options today and tomorrow, and let you know the pros and cons of each free file providers.

Tax refunds are sometimes delayed, often for inexplicable reasons. In many cases, you can track your tax refund online using the Where's My Refund? applet on the IRS Web site. This look up tool, however, only tracks a refund for the most current tax year. So if you're trying to find out about your refund from 2007 or an earlier year, you'll need to call the IRS. They have a special toll-free hotline just for refund inquiries at 1-800-829-4477.

Normally, you should allow eight to twelve weeks for a refund check to arrive in your mail box. If it's been longer than twelve weeks, it's definitely time to call the IRS. If it's been much longer than twelve weeks, you might want to contact the Taxpayer Advocate Service. Twice last year I had to call in the Taxpayer Advocate to find refunds that had been delayed for well over twenty four months. This doesn't happen very often, but when it does happen, it's good to let the Taxpayer Advocate get involved so they can identify if there are any systematic ways to prevent similar problems from recurring in the future.

The final estimated tax payment for 2008 is due on Thursday, January 15th, 2009. To avoid the penalty for not paying enough estimated tax, it's best to pay in at least 90% of your 2008 tax liability or 100% of your 2007 tax liability, whichever of the two numbers are lower. Both estimated payments and withholding are combined to help you avoid this penalty.

You have the option of skipping the fourth estimated tax payment. The IRS will not assess the underpayment penalty if you file and pay your tax in full by January 31st.

Personally, I find it best to get a rough calculation of my 2008 tax liability by drafting out my tax return, then using that to figure out the least amount I need to pay by January 15th to avoid any penalty. This process also gives me an idea of how much I might need to pay by April 15th.

Related information:

• Where to Mail Estimated Tax Payments (IRS.gov)
• Electronic Federal Tax Payment System

April 15th, 2009, is the deadline to file personal income tax returns. But there are other important tax-related deadlines, including deadlines for sending in estimated tax payments and making contributions to individual retirement plans. This year the IRS is providing an easy way to import their calendar of deadlines into your favorite calendar application such as Outlook or iCal. I was able to import the iCal into my Google calendar, thus displaying the important tax deadlines right in my daily schedule.