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As I was hanging out in Best Buy last week while my car speakers were getting replaced, I wandered over to the software section to check out the tax programs.
For the past couple of years, I've used H&R Block TaxCut to file our taxes (how do you file yours?) with little problem.
This year, however, it's going to be a bit more confusing.
Since we moved in the middle of 2007 (well, November), we'll have to pay state taxes in both Massachusetts (where we moved from) and Maryland (where we now live).
Perusing the TaxCut software, I noticed that every version only comes with one state. So I'll only be able to use the software to file in either Maryland or Massachusetts.
Thankfully, Maryland lets individual taxpayers file online for free with their "iFile" system. Check out the demo online.
Chances are, I'll probably use TaxCut for federal and Massachusetts and iFile with Maryland.
Do you have a confusing tax situation? Let us know about it.


While it's true that you generally only get one state with tax software, I know that with TurboTax you can purchase additional states for $9.95 (or something like that).
I've done the move-between-states before and simply purchased two states in TurboTax. It figured out when I moved, how much I owed in each state, and was able to file both states for me without issue. It actually ended up being pretty straightforward…
Good luck!
I work at H&R Block, in TaxCut Product Management.
Most of our software products include one free state. You can then purchase an additional state as well.
This will allow you to complete the filing requirements for both States you live in.
Good luck!
Derek — is the extra state purchased online/through the software, or do you need an additional box to get it?