A few weeks ago I posted my price comparisons for tax preparing and filing options. This is primarily of interest to those with an AGI above $50k as there are plenty of free options for the rest of you folks 🙂

I was excited to find an option that would only cost me $9.95 total to prepare and e-file both my federal and state returns. The only requirement was that I completed my returns prior to February 15th.

The main problem with eSmartTax is that I could rarely move to the next page in my preparation process due to a server side timeout. What that indicates is that they do not have a powerful enough setup to handle the demand and the result is a service that is all but inaccessible. I tried the service before January 31st, I tried it in the middle of a weekday afternoon and I tried it late at night. I always had difficulties with pages timing out. I was able to get most of my information in on one lucky attempt but have been unable to fill in some gaps now that all my documents have arrived and after multiple attempts I am giving up and will choose another method.

Even if their servers were humming along I found other issues with eSmartTax that would prevent me from recommending it. The company that runs eSmartTax apparently got it’s start providing electronic versions of forms inside applications like Microsoft Word…and it shows! The interface struck me as such a mid-90’s approach and very dated. If I wanted to just fill out tax forms, I’d do it on paper….with a pencil! To me, the power of tax software is an ability to guide a lay person through the filling out of the forms through questions and a clean interface. If you are very comfortable with tax forms, eSMartTax’s forms may not be a problem but for the average person I thought this poor interface was not worth the few dollars potentially saved.

And finally, any tax-filing site that hides their customer service contact information under the site map is bozo-tastic in my book. That’s just a deal-breaker.