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It's bad even when it stays free. Massachusetts has a tax site (which seems to be created and run by Intuit) which you can use to file for free. It, however, has been built purposefully to make it much, much more difficult to use than the paid version (that they push hard when you file your federal taxes with TurboTax).

The free version does very little error checking prior to submission. It won't even check for things like empty fields that are required for everyone (e.g. the field for your birthday on the state health care form).

The state paid for the free version with tax money and it lacks fundamental usability.

  * Doesn't perform basic validation
  * Doesn't calculate fields that can be automatically calculated (though there is a button you can press which will fill some of them)
  * Takes 24-48 hours for "processing" after submission before you are notified of acceptance.  In actuality, this tended to be 4-15 hours, but still... it's just doing basic validation.  I got rejections for empty fields and miscalculated fields (ones that I shouldn't even have to enter at all.)
  * Reports errors in a obscure manner, which makes it a chore to determine what is wrong (violates "Business Rule F1-1025", etc.)
  * Amounts to an electronic version of the paper form, where it only really does exactly what you put on it... add incorrectly: won't be detected, skip a line: no problem
  * I could go on, but you get the idea
If you use the paid product that is available from the same company (Intuit), it will handle all of the above automatically. So really we have is a company that has made a crippled version of software they are already selling. They double-dip with a lot of people this way and they don't compromise sales on the paid product. If you wait until the last day to file using the free site, you are unlikely to get it accepted in time since you won't have a second chance for submission.

The product built for the state could just be a really poorly written and managed contract, but knowing the way Intuit behaves generally, I doubt that is all that's going on.

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