Yup, known risk of hyper-legible IRS requirements and best efforts (but pretty good) banking system. Cash-basis (most personal and tiny-business accounting) is strictly based on “when money changes hands”, which is ambiguous in many transactions. If you have the documentation that you submitted the ACH before midnight local time on Dec 31, it’s “probably” ok (obDisclaimer: not legal or financial advice). Your accountant may have a different opinion, based on risk and hassle if someone decides to make a stink about it. There are written guidelines, but not enough case law to know exactly how it’ll be enforced, and in fact it almost certainly won’t be enforced. And if it is, the penalty will only be the tax difference plus interest (plus hassle and accountant fees, which are probably the bigger worry), as you had no intent to defraud.
On the object level, if you have investments at a broker and make significant donations, I HIGHLY recommend setting up a “Donor-Advised Fund” with your broker. This is an account to which you can donate money AND securities (which are liquidated at donation time), and get to count as a donation of appreciated value in the current year without reporting capital gains. You can request (which is always honored) donation to any legal charity at any time, with no tax consequences about the timing of the donation. Value donated but not yet directed grows in a money-market fund.
This means your annual tax choice is only about HOW MUCH to donate (and what unrealized capital gains to donate with it). The choice of WHO and WHEN to give it is decoupled from taxes.
Yup, known risk of hyper-legible IRS requirements and best efforts (but pretty good) banking system. Cash-basis (most personal and tiny-business accounting) is strictly based on “when money changes hands”, which is ambiguous in many transactions. If you have the documentation that you submitted the ACH before midnight local time on Dec 31, it’s “probably” ok (obDisclaimer: not legal or financial advice). Your accountant may have a different opinion, based on risk and hassle if someone decides to make a stink about it. There are written guidelines, but not enough case law to know exactly how it’ll be enforced, and in fact it almost certainly won’t be enforced. And if it is, the penalty will only be the tax difference plus interest (plus hassle and accountant fees, which are probably the bigger worry), as you had no intent to defraud.
On the object level, if you have investments at a broker and make significant donations, I HIGHLY recommend setting up a “Donor-Advised Fund” with your broker. This is an account to which you can donate money AND securities (which are liquidated at donation time), and get to count as a donation of appreciated value in the current year without reporting capital gains. You can request (which is always honored) donation to any legal charity at any time, with no tax consequences about the timing of the donation. Value donated but not yet directed grows in a money-market fund.
This means your annual tax choice is only about HOW MUCH to donate (and what unrealized capital gains to donate with it). The choice of WHO and WHEN to give it is decoupled from taxes.