What controls if a property tax prepayment is deductible?

As we all probably know here by now :), the presumably soon-to-be-law tax bill does not deny a deduction for 2017 prepayment of 2018 property tax (like it does for income tax).
However, IIRC you can't (and could never) take a full deduction for arbitrarily pre-paid property tax. So if you for example (and to be silly) pre-paid 5 years worth of property tax in 2017 you would not be allowed to deduct that entire payment in 2017.
So what is the line? Can you take a deduction for a prepayment of what you'd "reasonably" expect you'd have to pay in all of 2018? Are you limited to only part of 2018? Are you limited to what you've actually received a bill for by the end of 2017? Are you limited to what's been assessed?
In my specific case, our town operates on a July 1-June 30 fiscal year. Sometime after July 1 they make an estimate as to what assessments will be and the August 2017 (FY2018) and November 2017 (FY2018) bills will be based on that estimate. Eventually they set the actual assessment and actual total FY2018 tax to be collected then the Feb 2018 (FY2018) and May 2018 (FY2018) bills will each just be half the difference between the total actual tax and the estimated tax they billed for in Aug and Nov).
Is my deductible prepayment limited to just paying off the rest of the FY2018 tax? Or can I deduct in full a prepayment for everything I'd reasonably expect to pay in calendar 2018?
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On Tuesday, December 19, 2017 at 3:47:28 PM UTC-5, Rich Carreiro wrote:

I haven't read the final language, but my understanding is that as a cash-basis taxpayer, you can deduct payments made in 2017 for any currently deductible tax that has already been assessed and billed. So RE taxes which would normally be due in Feb/May 2018, but were actually billed in 2017 are fair game. You wouldn't be able to prepay taxes which aren't assessed until 2018. The fact that the municipality calls this "fiscal year 2018" is irrelevant. The tax bill will have language such as "... is (not) applicable to tax years beginning before (after) [specific date]".
Ira Smilovitz, EA
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Well, that comes down to what "assessed and billed" mean. The muncipality mails the bills Jan 1 (due Feb 1), April 1 (due May 1), July 1 (due Aug 1), and Oct 1 (due Nov 1). So you would apparently be saying that I couldn't deduct any prepayment, even if I knew what the amount would be, because no "due in 2018" bill was actually received in 2017. (Not arguing with you -- just making sure I understand what you are saying).
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On Tuesday, December 19, 2017 at 4:22:30 PM UTC-5, Rich Carreiro wrote:

I'm not sure that I'm saying that. I think it's more like an installment loan. If the amount is set before December 31, and you can pay it at any time before it is "due", but you have the option to make the total payment over 4 quarterly payments, then any 2017 payment should be deductible. On the other hand, if you generally can't make a given payment before a certain date, If you can go into the tax department and pay the remaining balance "today" then it's deductible when paid.
For instance, my municipality in NJ also mails bills quarterly, but I get a bill with all four quarters listed sometime in the late summer/early fall. (They don't always have the final amount ready before the August payment is due.) I believe that my Feb/May 2018 installments will be deductible in 2017 if I make them before December 31. Caveat, I haven't read the final bill language and I could be wrong. For anyone else in NJ who reads this, note that prepaying your 2018 real estate taxes in 2017 could affect the RE tax deduction/credit on your 2018 NJ-1040.
Ira Smilovitz, EA
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My town does the same thing as Rich. However the property assessment, which determines the value is done in December 2017.
The exact values of the 8/1 and 11/1 amounts due are known now even though they won't be put on a bill until June because they are based on the December property assessments.
Are these taxes considered "assessed"?
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On 12/19/17 3:42 PM, Rich Carreiro wrote:

I trust you over a CNBC writer I don't know, but this article implies prepayment of either isn't allowed.
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My accountant says I can deduct invoiced property taxes which are due by feb 2018
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The evening news says that NYS has authorized prepayment of property taxes. Presumably that means that I can pay my August School tax in 2017 and get deduct it? Right?
I posted this a few hours ago, but it was rejected for top posting. ?
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As far as I can tell, if they've issued a tax warrant, yes. No idea if they issue a warrant that far ahead.
Here in the upstate boondocks, the town and county tax bills arrive this week with a due date of Jan 31. In the past they haven't accepted payment before Jan 1, but this year they do.
R's, John
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On Friday, December 22, 2017 at 8:47:58 PM UTC-5, Frustrated wrote:

The answer is a definitive "maybe". You need to contact your local tax authority. The sort of general rule is if you've been billed for it already, even if the due date isn't until 2018, you can pay and deduct in 2017. But the specific answer depends on your local tax authority's practice. Some (perhaps all) NYS RE tax that you have a coupon for can be paid now.
Ira Smilovitz, EA
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Do remember that if you are in AMT territory pre-paying probably won't help.
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