Assuming that the employee maintained the SIMPLE account for over 2 years, may an employee rollover his SIMPLE IRA into a ROTH IRA (assuming he meets the AGI requirements)?

If so, how would this work? Is it automatically considered a conversion ROTH?

Yes. The Roth IRA regulations state: An amount in an individual's SIMPLE IRA can be converted to a Roth IRA on the same terms as a conversion from a traditional IRA, except that an amount distributed from a SIMPLE IRA during the 2-year period described in section 72(t)(6), which begins on the date that the individual first participated in any SIMPLE IRA Plan maintained by the individual's employer, cannot be converted to a Roth IRA. Pursuant to section 408(d)(3)(G), a distribution of an amount from an individual's SIMPLE IRA during this 2-year period is not eligible to be rolled over into an IRA that is not a SIMPLE IRA and thus cannot be a qualified rollover contribution. This 2-year period of section 408(d)(3)(G) applies separately to the contributions of each of an individual's employers maintaining a SIMPLE IRA Plan.

Once an amount in a SEP IRA or SIMPLE IRA has been converted to a Roth IRA, it is treated as a contribution to a Roth IRA for all purposes. Future contributions under the SEP or under the SIMPLE IRA Plan may not be made to the Roth IRA.

Since EGTRRA has become effective, does anyone know whether a SIMPLE IRA that has been held longer than 2 years can be transferred to another IRA or eligibile retirement plan. IRC 408(d)(3)(A) and (G) seem to indicate that such transfers and rollovers are permitted. Thank you.