It Took 3 Tries But I Finally E-Filed My Taxes

When I say that it took three tries, I mean that I had to try three companies before I found one that could correctly process my information for my 2007 tax return. The three companies I tried were, in order, TaxSimple, TurboTax, and TaxAct.

While I filed via the internet last year, I do not believe I used any of these companies before. You may ask why I did not just reopen an account or file with whomever I used before, but there are certain problems with that. First, one must go thru the IRS.gov site to a tax preparer in order to file for free. Second, different companies offer free taxes with different qualifying terms and income limits. A ceiling of $54,000 is common, but many use upper and lower age limits, or have other restrictions.

So, I went to the IRS site, which makes me nervous enough but I stick it through because I know I will not be there for long.

I actually click on "FreeFile" on the left. It takes me to a page where it queries, "Are you trying to file a 2007 tax return?" If your adjusted gross income was $54,000 or less in 2007, you can use Free File to prepare and e-file your taxes online. Click the Start Now button. After having wrung myself out preparing my taxes with paper and pencil, I can hardly believe I am actually asking to be tortured. But after a few years of using either a TurboTax software package or filing online, I have been desensitized (this is a psychological term) enough to restrain myself from tearing out hair.

So anyway, I started about a week ago already. I first picked a company called TaxSimple. I figured they would keep things -- simple. Simply aggravating. One major feature of their software is that it takes over your whole computer screen. I don't know if I would have been able to minimize the window so as to search for documents within the computer or not, but it looked as though there were no minimize button. One could not even use one's browser or toolbar buttons to print or copy.

So then I came to virtually the end of the tax return with them, and we start running into problems. I found it hard to find out what the problem was exactly. Then I realized that one problem was that it rejected my checking account number for the automatic deposit of my tiny refund. Fine, I told myself. I will just print it out and fix the problem MANUALLY -- and I realize I was being hopelessly archaic but I felt my back was to an unsympathetic wall.

The copy of the return that was emailed to me was locked with a password. Yes, I had my password, which I had sagely written down as it was created. But my password produced no "Open Sesame" moment.

I was screwed.

By this time it was late. I did email a complaint to the customer service window, but that produced an unhelpful listing of the steps to open the file -- which would have worked if they had not scrambled the password somehow.
I needed a few days to get my head together again. My schedule was a bit crazy for most of the week, so I let it lie. Friday came and I was feeling less like the world was out to get me, so I girded my loins, as they say, and took my battle axe to the internet again.

First stop was the friendly e-skies of the IRS once more. Click on FreeFile, etc.

This time I decided I would pick that old war horse, the trusty and reliable Turbotax. They could never let me down, could they? Could forty million (I made up this number) taxpayers be wrong?

Yes they could.

I was proceeding swimmingly on a crisp, clean module when I ran into a dead end. The free file would only cover basic forms, such as the W-2, and forms for interest and dividends. But I had sold off part of an asset last year, and that form was not included. Of course, the nice people at Turbo would transfer my data automatically to a new, paid return form. This return would cost me about $50. I closed out of the return and their site. Adios, Turbo. You have lost me for good with your bait-and-switch gambit.

So, back to the ever-loving arms of my friend, the IRS. Shudder. We must stop meeting like this, I thought. Click on FreeFile, with a tiny whisper of hope refusing to die in my heart.

Third time is the charm, isn't it?

It was beginning to feel like I was spinning the wheel at Monte Carlo and everyone else was betting 22 and I had my chips on 7. And like the wheel at Rick's back room in Casablanca, this wheel was rigged to hit on 22 this time out. And no one had told me!!

Oh, it's only money, after all. With fingers crossed I picked out TaxAct. The crisp clean module resembled TurboTax in many ways. One difference was that when filling in data on dividends, for example, there were fields to fill in the proper identifying names and numbers for each stock or fund. One had to kind of squeeze all that into one field, if at all, into TurboTax. I was thinking this might trigger an audit if the IRS decided it needed to verify the actual tax number for each fund?

This was not the fastest form, but the TaxAct form was the most thorough, taking you through all the fields of a given 1099, for example. This may irk some filers who have very basic information to key in, but those with more complicated arrangements ought to be happy that they are prompted to fill in all the blanks.

So at last I came to the end of the tax return, sat through all the "checking return for any red flags" and so forth. It accepted my checking account number for a deposit without any problem. I was asked if I would like to also file the state return. Normally, I have gone to the state's own tax page to file, but after making so many treks to the IRS and state, I was beaten down. I just wanted to be done. They won. I had to pay a very modest fee for also filing the state return, but the two returns were processed seamlessly and without any further snafus.

This is my little saga of filing for free online. There is nothing like having the correct form called up instantly from the preparer's files, compared to hunting for printed forms at the post office or library. The process should not have run into dead ends with TurboTax -- they should have stated up front that they only handled certain forms and schedules for the free e-filing. And TaxSimple has a ways to go to make their service run as smooth as their name implies. But the hunt for a painless tax experience was well worth it for me.

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