Last year I had this situation happen at least a half a dozen times. Getting pretty frustrated. Not sure what has changed. I have used the same bank (also had it happen with my Ally account, so more than one bank) and have used their bill pay for as long as I can remember. This year is the first I have had this issue.

They cut a check for the bill pay - first questionable thing when the payment is going to someone like Chase for a Mortgage - why the heck would they not be able to do electronic payment to them? IF I do it the other way, go to my Chase mortgage account and pay from there, it goes electronically. So is my bank playing some sort of financial float game now that interest rates are higher? Then after x days they remove the money from my account. Not because the check cleared. Just because, it would seem. Where does this money go while waiting for the check to clear? Why is it okay for them to be withdrawing money from my account before the vender being paid cashes the check? If I wrote the check that would not happen and I would KNOW that the check was cashed by the payee when it cleared my account.

I understand that the problem is being made worse by the state of the Postal Service. The bank is not responsible for that.

My issue is that I know the payment is set up. I see it go out as pending. Then I see the amount clear/removed from my account. Unfortunately, I can no longer assume that means the vender was paid. But with both Texans and Ally, it is hard / requires multiple steps and/or contacting them to see if the check actually cleared. So being a busy person, inevitably my first notice that the check wasn't received is the vender contacting me.

Starting to really piss me off. Not getting any real answers from the bank.

I generally dislike letting venders/payees withdraw from my account. So I have always avoided setting things up that way and preferred controlling it through the bill pay service. But now I am starting to question that.

WTH is going on!?!? Seems kind of ridiculous in modern times that I would need to go back to paying bills with my checkbook and stamps.

Generally, with a bill pay system, the bank removes the money from your account and puts it into another account with a lot of other people's money that are using the same service to bill pay. The bank then issues checks for everyone's payments from that account. These checks are printed with the information you supplied (e.g. your vendor account number) and then put into the mail. In some cases, checks are not issued and an electronic payment is made.

So why is there a "middle man" account? Lots of reasons, but here are two big ones: 1) this is easier for a bank to manage, control, and keep deposits, and 2) importantly for you, that check that got issued to pay your bill does not have your personal account details on it (e.g. account number). If someone takes that check out of the mail and lifts the account number off of it, they are not stealing your details, they are stealing the bank's details.

Bill pay is generally fairly safe. But as with any banking product, you do actually want to read the terms of service because there can be differences bank to bank.

All that being said, you have a few other options for paying your bills. 1) credit cards - earn points/rewards and pay your bill on time, 2) third party payment processors (PayPal, Zelle, etc.), 3) EFT (but you'll need the vendors banking info and some refuse to give this out). Unfortunately there are some things with limited options, a mortgage or rent tends to be most people's unavoidable direct draw or check. I think Centerpoint is another one, which is sort of bizarre since its a cheap bill for most people. Many other vendors will give you a discount to do a bank draw but also offer a credit card option - they want to avoid the credit card processing fee, which is why you will see this (Verizon is an example of someone who offers this).

Bank bill pay is an anachronism. Just set up direct drafts. You'll always know who took what and when and all is traceable if you need to dispute.