Tag72: "My question is twofold and it is for my brother. He is doing his taxes on HD Vest. He was sent 2 - 1099 R forms from the IRS. One of those was from his wife's 403b rollover to a Roth IRA. Another one was from a job switch where he had a 403b with Fidelity, but because he switched school districts, he had to fill out another 403b rollover to his current job still under Fidelity. It says on both the amount of rollover and under box 4 it has no fed taxes withheld. It tells him on those 1099 R forms to report those amounts on his tax forms. So, my question might have been already been answered by me, but he does need to put that somewhere on his return, correct? And that should not count against him correct? I just want to make sure. "

I am no tax expert (and I am sure that they will be along), but the first part of your statement sounds incorrect --- I do not believe that anyone can go directly from a 403b plan to a Roth IRA without first stopping (however briefly and metaphorically) in a traditional IRA AND conversion from a traditional IRA to a Roth IRA is usually a taxable event.

At least a start. Regards, JAFO