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In Oct 1999, I opened a Roth IRA and contributed $2000. In January 2000, I made another $2000 contribution.

Now I'm doing my taxes. Oops, with overseas income and capital gains, I'm not eligible for a Roth. I'm reading up on recharacterization; I can open up a traditional IRA (non-deductable) and recharacterize. All things staying the course, I probably won't be eligible for a Roth in 2000 either.

1) Do I just recharacterize the whole $4000 and the earnings now, or only $2000 this year and $2000 next year?

2) Recharacterization should generate a 1099-R from somebody (the old Roth IRA trustee?). Do the numbers on this 1099-R get reported in 1999 or 2000? If this recharacterization is reported in 1999, does that mean I have to file an extension while I wait for the new account to be opened and the 1099-R mailed to me?
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