<prompt> Human: Do I need to report my 1099-R? I basically left a job, moved money from my 401K at the job to a Rollover IRA and then transferred from the Rollover IRA to a Roth IRA that I previously set up? Do I need to report that?  <response>: Yes, thats a huge taxable event. A 401k and rollover are both pretax contributions. By transferring the Rollover IRA to a Roth IRA, you made the entire balance Income this year, which means you owe taxes on the full balance as if it were income. 