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Have you ever lost a bill pay check or have someone follow up and say they didn’t receive it?

With BillPay, they deduct the amount you pay on the day of, the banks take their sweet time to send the check because they want to slow down the money.

If you lose the check, it’s a lot more overhead to cancel and get your money back.



My bank does not take the money out before it's cashed by the receiver


Seconded. Any bank that does is not a bank I would use.


I've had landlords who would deposit checks with inconsistent timing -- sometimes several weeks after they received the check.

This results in a situation where the amount of money you have available to spend might be $rent lower than you actually think, unless you've determined whether the landlord has cashed the check or not. When I was the one writing the checks for an apartment I shared with my also-just-out-of-college roommates, that check was pretty big, often >50% of the value of my checking account.

While I'd appreciate the extra interest that I'd earn on that money sitting around for an extra few weeks, I'd rather have the certainty of knowing how much money I actually had.

(If the bank could show an effective balance, where the check is shown as a pending transaction, I suppose that would be fine too.)


That's why one records the check amount in a ledger kept electronically or physically with the checkbook. You will then always know what you have even if the pesky landlord waits 3 months to cash a check. It's old school but works flawlessly for one person.

(Dunno if banking apps have the ability to record written checks then automatically reconcile when those checks clear. It'd be a nice banking app feature but would reduce revenue obtained from overdraft fees, on which banks gorge.)

For a couple, one needs the has-the-checkbook? mutex to write new checks. Each spouse having a credit card paid down monthly reduces the mutex contention for negative cost (considering float and rewards, ignoring credit-only prices).

Supposing the above fails from time-to-time, there's a defense in depth approach: If you write those checks from a margin-enabled brokerage account, anytime you make a mistake you self-fund the overdraft. This can be useful if the checks you write in a month are small relative to your margin collateral. This can also be useful if one occasionally needs to write a check for larger, one-off purchases where it'll take a few days to move the money around to satisfy the check. This is conceptually nice because a negative checkbook balance stops being haltingly terrifying if you know a regular paycheck will land before some checks clear. Do not trigger margin calls on yourself!


> the banks take their sweet time to send the check because they want to slow down the money.

Maybe some shit banks, but a decent bank like Ally will try to have the check delivered by the due date chosen (mailing out a few days prior). There isn’t much money to be made this way. If you knew they were always late you’d just adjust the date back anyway. Decent banks don’t play petty games like this.

For electronic payments the money is withdrawn similar to an ACH, for paper checks any reputable bank will withdraw the money only when the check is cashed.




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