When converting from an IRA to a Roth, do I have to file self-employment tax?

The Roth IRA conversion is a great opportunity but it is really important to understand the mechanics of the process and the economics as applied to your specific financial situation.

To directly answer your question, the conversion of the IRA to a Roth IRA will not trigger any self-employment taxes. In addition, if you convert in 2010 you can essentially get an interest free loan from the government. The income tax from the conversion is not payable until you file 2011 and 2012 returns -- half in each year.

Keep in mind that there are so many variables to consider so it is nearly impossible to quantify whether there is an advantage to convert or not without having all of the facts.

I would strongly recommend that you do some scenario analysis comparing what tax bracket you are in now and what you think you might be when you begin taking distributions. Apply those assumptions to a Roth conversion now, verses keeping the funds in a traditional IRA or any other option you are considering.