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Penalties on monies I've already been taxed for? That's odd.

No, penalties for filing late.

Probably just being paranoid, but I do want to be sure an 8606 is present every year we did this (which has been the past three or four years, at least).

Yes, in order for the IRS to recognize the basis (i.e. already taxed contributions) in your IRA, there needs to be a Form 8606 filed for each year that you made those after-tax contributions.

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