I just finished filing my 2006 taxes, an activity made significantly more difficult by TurboTax. The desktop edition of TurboTax was unable to update itself, on my PC running Windows XP, despite hours and hours of trying. The one-click update didn't work; it didn't give me any feedback at all about whether it succeeded. The manual update looked like it worked, but the application kept telling me that I needed to get updated forms, which were not yet available from TurboTax. In September of 2007, the software promised that the forms would be ready by January 12, 2007. Er, what? In October of 2007, I got email from TurboTax saying that those forms were now ready -- bizarre since everyone else needed these forms in April 2007. (I'm not talking about obscure forms here; just Schedule C.) So I try again to update my desktop TurboTax, and once again it fails. I go through some insane machinations from the support site ("open the command prompt and run this command: ping -mysterious -incantation) to discover that my fragment size was insufficent. More TurboTax forums, and I learn that I have to set the MTU size on my router. Joy, joy -- my cable gateway (blazingly fast, blazingly expensive) doesn't allow the user to set the MTU. I don't blame Cisco, here -- I blame TurboTax, for not being able to cope with a net connection that handles everything else I throw at it. BitTorrent? Fine! Downloading 50mb installers? Fine! Sustained ssh connections for days? Fine! Downloading tax forms: nope. Ridiculous.
At this point I mailed Intuit for support. They got back to me a few days later, and told me to do the things I had already done, which I had explained in my support request that I'd already done them. They told me to call them for support during business hours. I have a job, people. TurboTax was supposed to be convenient and there was supposed to be readily available technical support.
But I needed to get my taxes done, and I could see that getting on the phone with them wasn't going to be helpful. I realized that I could avoid this subtle network incompatibility if I used the web-based TurboTax. Alas, web-based TurboTax can't import an incomplete return from desktop TurboTax, so I had to re-enter all my information. The tab key didn't work as nicely to move between fields as it did on the desktop application, but it was usable. After spending an hour or two filling out forms, my taxes were submitted and accepted.
The lesson for TurboTax is... if connecting with your big fragment sizes fails with a desktop application, try making the connection over http or https. Yes, even desktop applications can connect over http.
And: Intuit, make live tech support available by phone 24/7 before October 15, not just before April 15.