Are prepaid medical expenses deductible the year the payment is made or the year the prepay is applied to medical services rendered?

[itonewbie · Accepted solution]

So long as the expenses otherwise meet the requirements for deductibility, I would say yes.  The following from §1.213-1(a) should support this:

Except as provided in paragraph (d) of this section (relating to special rule for decedents) a deduction is allowable only to individuals and only with respect to medical expenses actually paid during the taxable year, regardless of when the incident or event which occasioned the expenses occurred and regardless of the method of accounting employed by the taxpayer in making his income tax return.