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If you are worried about having proof you paid the IRS, just use EFTPS.
https://www.eftps.gov/eftps/
PSU

======================
That's certainly an option. In addition, for individuals, IRS' Direct Pay option is just as easy and doesn't require you to be a regular user, set up passwords, etc.

https://www.irs.gov/payments/direct-pay

And in case it's a concern:
Amount and frequency limitations
IRS Direct Pay won't accept more than two payments within a 24-hour period, and each payment must be less than $10 million. For larger electronic payments, use EFTPS or same-day wire.


Bill
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https://papers.ssrn.com/sol3/papers.cfm?abstract_id=3084187

There is going to be a lot of tax hijinks in 2018.

PF
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Hawkwin notes:

Some things you may want to do based on the possibility of the changes in tax law:

Prepay state and local income taxes for 2017.
Sell any securities where you had been previously selling individual lots based on cost basis. We may see a strictly enforced FIFO rule for stock - you may no longer be able to sell what is most economically advantageous for you.
Exercise deep-in-the-money nonqual stock options
Make any 2018 charitable donations in 2017
Payoff your HELOC - tax deductibility on interest may go away in 2018.
Don't make any gifts subject to the gift tax in 2017 if you can avoid it.
=== ===

ALSO, consider paying any real estate taxes in 2017 rather than waiting until January, 2018.
--BigBunk
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ALSO, consider paying any real estate taxes in 2017 rather than waiting until January, 2018.


Yes, I left that one off my list. I just called my local assessors office to try and do exactly that but they wont accept early payment it seems. Might call back and try to get a different answer from someone else.
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re: Exercise deep-in-the-money nonqual stock options


Care to discuss why?
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ALSO, consider paying any real estate taxes in 2017 rather than waiting until January, 2018.

Yes, I left that one off my list. I just called my local assessors office to try and do exactly that but they wont accept early payment it seems. Might call back and try to get a different answer from someone else.


Under current Federal tax law, isn't when you write the check that is important rather than when the check clears your bank?
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Under current Federal tax law, isn't when you write the check that is important rather than when the check clears your bank?

I believe the date the check is mailed is the important date. Writing a check and letting it sit on your desk for 3 months won't work. Writing a check with the reasonable expectation that it payment will be returned doesn't cut it either.
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I believe the date the check is mailed is the important date.

And how does one prove that? Neither a tracking number or a delivery receipt offers no proof that payment was sent.
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I believe the date the check is mailed is the important date.

And how does one prove that? Neither a tracking number or a delivery receipt offers no proof that payment was sent.

The post office provides various ways of proving date of mailing. The simplest is a "Certificate of Mailing" which I believe is accepted in court, but not by the IRS. Generally I use the Certificate of Mailing when mailing notices to tenants.

Then there's Certified mail which is accepted by the IRS.

https://www.usps.com/ship/insurance-extra-services.htm?
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BTW, unless something with legal significance, such as a tenant notice or tax payment is being sent, ordinary mail is used. The IRS will just have to trust me that it was mailed it on December 31, and not January 1st.

Generally, if I'm concerned I'll mail it a week earlier so the check is likely to clear by the EOY. Plan in advance and all these minor concerns go away. If payment is made electronically, such as making next year's property tax payment December 31 this year, the bank has the necessary proof.
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The post office provides various ways of proving date of mailing. The simplest is a "Certificate of Mailing" which I believe is accepted in court, but not by the IRS. Generally I use the Certificate of Mailing when mailing notices to tenants.

Then there's Certified mail which is accepted by the IRS.


That says nothing to the contents, but only that a letter was sent/received. It does not prove a check/payment was enclosed.

Certified mail is good for the sender's peace of mind, such as your mailing notices to tenants. If you need to prove payment, you'll need a receipt.

So do that if you like, as for me, if I'm going to claim a tax deduction, I'm going to have proof such as a banking transaction, credit card statement, or recipient receipt.
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That says nothing to the contents, but only that a letter was sent/received. It does not prove a check/payment was enclosed.

True, however, the recipient will have to explain what was received if not what you said was sent. Also, if it's good enough for the IRS and the courts it's good enough for me.
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"Also, if it's good enough for the IRS and the courts it's good enough for me. "

It's only good enough if you sent your money to the IRS....and they took a while to post it.

Most taxing boards will issue you a receipt and that is the date the taxes were paid, regardless of when the 'check was mailed'.

Heck, you could claim you sent in $15,000 in real estate taxes on something you don't even own, take a deduction, get money from the IRS, then file an amendment later changing that, and never send in a check to pay taxes due. or other stunts.....

t.
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Heck, you could claim you sent in $15,000 in real estate taxes on something you don't even own, take a deduction, get money from the IRS, then file an amendment later changing that, and never send in a check to pay taxes due. or other stunts.....

There are numerous ways to commit fraud, let's not.

Jack
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If you are worried about having proof you paid the IRS, just use EFTPS.

https://www.eftps.gov/eftps/

PSU
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If you are worried about having proof you paid the IRS, just use EFTPS.
https://www.eftps.gov/eftps/
PSU

======================
That's certainly an option. In addition, for individuals, IRS' Direct Pay option is just as easy and doesn't require you to be a regular user, set up passwords, etc.

https://www.irs.gov/payments/direct-pay

And in case it's a concern:
Amount and frequency limitations
IRS Direct Pay won't accept more than two payments within a 24-hour period, and each payment must be less than $10 million. For larger electronic payments, use EFTPS or same-day wire.


Bill
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Exercise deep-in-the-money nonqual stock options

Only if you are subject to AMT in 2017.
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You might want to get the 2017 version of Turbo tax and run the iterations to see what the impact is. That way, you can maximize the deductions.
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