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Hello - Thank you again for the additional information.  It appears that a direct rollover from a traditional 401K to a Roth IRA is simpler in paperwork/documents?

 

1.  From traditional 401K to Roth IRA (one 1099R and one 5498)

    -  One 1099R from the 401K administrator (sender), showing rollover amount of $20,000 (as an example)  in box 1, and 2a (taxable amt) in the same amount.  code G in box 7.  This is fully taxable.

    -  One 5498 from the Roth IRA (receiver), showing the Roth IRA receipt, for recordkeeping only.

    -  Tax return would show the rollover amount of $20,000 in 5b (Pension and annuities, taxable amount), with a notation of "ROLLOVER" (the notation is generated by the TurboxTax software).

 

2.  From traditional 401K to traditional IRA, then from traditional IRA to Roth IRA (two 1099R and two 5498)

   -  One 1099R from the 401K administrator (sender), showing rollover amount of $20,000 (as an example)  in box 1, and $zero in 2a (non-taxable).  code G in box 7. (non-taxable)

   -  One 5498 from the traditional IRA (receiver), showing the traditional IRA receipt, for recordkeeping only.

   -  One 1099R from the traditional IRA (sender), showing rollover amount of $20,000 (as an example)  in box     1 and 2a (taxable amt) in the same amount.  code 7 in box 7 (I am over 59 1/2).  This is fully taxable.

   -  One 5498 from the Roth IRA (receiver), showing the Roth IRA receipt, for recordkeeping only.

   -  Tax return would show the distribution of traditional IRA (Roth) in 4b, taxable amount of $20,000.  Would it also show the rollover of 401K to traditional IRA in 5a and 5b and say (Pension and annuities), with a notation of "ROLLOVER" (the notation is generated by the TurboxTax software), but zero taxable amount? Like if I have a pension of $30,000 and 401K rollover of $20,000 - would it show $50,000 in 5a, and $30,000 (taxable pension) in 5b?

  -  you also indicated there would be a form 8606 generated, with part II showing the distribution of IRA to Roth IRA?

 

Thank you again.