I've changed jobs, rolled my 401k to a Traditional IRA, then rolled that to an existing Roth Conversion IRA, all in 1999. The 401k had my contributions, the company matched contributions, and capital gains on both. Do I pay taxes on the total amount, and how is it taxed- as earned income or capital gains or a combination?

When rolled to the traditional IRA, your pre-tax contributions, company contributions and earnings were not taxable. However, when the traditional IRA was converted to a Roth IRA, the amounts converted which were not previously taxed (i.e., the entire value of the traditional IRA in this case) are included in income. They will be taxed as ordinary income, not as capital gains.

Hope this is of benefit to you.

I'm currently contributing to a company 401(k) but I'm interested in rolling-over a portion of my savings to a roth education IRA. Is it legal to remain in my 401 (k) and a roth IRA at the same time?