Converting to Traditional IRA to Roth IRA

[dmertz]

That's an interesting thought.  However, without actually removing the excess $1,500 from the 403(b) with a corrective distribution, I'm not sure that a late rollover of $1,500 would qualify for self-certification that the rollover would qualify for a waiver of the 60-day rollover deadline.

I think that throughout this discussion we have assumed that you have no other funds in traditional IRAs; I'm not sure if that was clearly established.  If I was in this situation, I would probably proceed as if I had other funds in traditional IRAs that would have allowed  the $2,200 rolled over to the 403(b) to be all pre-tax and continue to carry the $1,500 of basis on Form 8606.  Future contributions to a traditional IRA and the investment growth on those would eventually allow you to recover the basis.  This would certainly raise the least attention with the IRS.  The only clue that they would have is the lack of any 2024 Form 5329 showing a nonzero year-end balance.

[tractng]

Yes the assumption is correct, I don't have any other funds in traditional IRAs.  Currently its at zero balance on the only traditional IRA account (at TIA).  I don't plan to make any contribution to this account.  I do plan to open one at Charles Schwab in a few years and move the 403b when I leave my job.

[dmertz]

I doesn't matter where the traditional IRA is held.  Your basis belongs to you, not to any particular one of your traditional IRAs.