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It looks like I will never be able to get last dollar of after tax money our of my IRA until all IRAs are completed exhausted (excluding roths). With this in mind, I will probably die with after tax money still locked away.

Although I don't enjoy dwelling on such matters, your heirs will thank you if you take the time to make sure the information about your pre-tax traditional IRA contributions is readily available and they understand how it works. The taxable/nontaxable calculation continues as your beneficiaries take distributions.

I had an option earlier this year when I rolled my 401K to take the after tax money as a check to me and just roll the pretax money into the rollover IRA. If had it to do over again, I would have taken that after tax money. Is there any avenue to recharacterize that rollover since it was done in 2005?

The way your luck is running today, you'll not be surprised that the answer is "no."

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