[koolba]

For companies operating on a cash basis with a standard Jan-Dec fiscal calendar (e.g. most small businesses), this would allow you to deduct future spending by prepurchasing AWS credits. It locks away whatever money you dedicate to it but that’d be peanuts compared to paying income tax on it in order to carry it forward as retained earnings.

[sokoloff]

I don't think that works the way you suggest, but I also admit the guidance is unclear.

Reg. Section 1.461-1(a)(1) provides the following:

If an expenditure results in the creation of an asset having a useful life which extends substantially beyond the close of the taxable year, such an expenditure may not be deductible, or may be deductible only in part, for the taxable year in which made.

https://www.law.cornell.edu/cfr/text/26/1.461-1

If you buy 10+ months of AWS credits in December and have a Jan-Dec fiscal year, I'd argue that you bought "an asset having a useful life which extends substantially beyond the close of your taxable year"

[binarymax]

This isn’t purchase of a capitalizable asset, it’s renting as an operational expense ;)

[gowld]

Why not use a dedicated escrow service for that, which wouold work with all expenses, not just AWS?

[koolba]

If it smells like a checking account then it’s going to be treated as a checking account.