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"As another example, you can put in $4000 in January 2000 and have $2000 count towards 1999 (assuming you have made no previous contribution for 1999), and $2000 for the year 2000."

Be safe. Send them 2 separate $2000 checks, each clearly marked for which calendar year it applies to. Include a cover letter explaining them. It may be nice to be able to show the IRS or someone 2 separate cancelled checks that way, if ever the need arises.
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