I am considering writing a check to pay off my braces all at once since it is an amount larger than 7.5% of my income.

However it is getting very close to the end of the year; if I write the check in 2010, and the check clears in 2011; will the payment still be considered part of 2010 on my tax write-off since I dated the check as 2010?

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According to IRS Publication 502:

If you pay medical expenses by check, the day you mail or deliver the check generally is the date of payment.

The quoted text can be found under the section titled What Expenses Can You Include This Year?

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  • 1
    Protip: Get a proof of mailing or send certified mail in case of an audit. – duffbeer703 Dec 30 '10 at 2:18

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