If I convert a Traditional IRA to a Roth IRA, do I owe any taxes?

Yes. Upon conversion, you will owe ordinary income taxes on your investment earnings and on deductible contributions you have made to your Traditional IRA. This amount is taxable income in the year the money leaves the Traditional IRA. Basically, you owe tax on any money that has not been taxed before. But you will have the opportunity to withdraw earnings made after the conversion, free of any taxes if you have meet the 5 year test.