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Serious question: Your Apple Cash account is tied to your checking account, correct? Is there a built-in 'overdraft' feature included - meaning that if I try to send $50 from my Apple Cash account and the balance is only $25, will the transaction fail or will it pull the extra $25 from my connected account?

If no, then I see the scenario you stated working... but if it does pull the difference from the connected account, the risk/exposure is still there and the process offers no form of additional protection from fraud or error.

That's a good question - it's not directly funded from a checking account. Instead, it'll show that there isn't enough to cover it entirely with Apple Cash and bring up an Apple Pay prompt and give you the choice to use any debit cards loaded in Wallet as the backup funding. These steps will require authentication either with Touch ID or Face ID w/double-click of the side button. There isn't a direct option of "when I don't have any money, pull from this account" and if you had multiple debit cards, any one of them could be selected as the backup.

You can put your routing/account information in as a way to get money out of Apple Cash (it's handled as a direct deposit), but you could always leave that blank and use any money in Apple Cash to either pay an Apple Card, a person, or spend.

Worth a read since they can probably explain it better than I can :):
https://support.apple.com/en-us/HT207881
https://support.apple.com/en-us/HT207882
 
I use Capital One 360 online checking account to pay for certain "subscriptions" that I don't want to forget about (ie monthly recurring subscription fees).
My main checking account is linked to the Capital One account and funds it as I need to.

It's my way of using a secondary checking account to prevent being over charged or forgetting to cancel a subscription.
 
I pay all my bills online. Most sites give you the option to pay by debit or credit, or with a bank account number. Most ask to save your payment information for future payments but it is not mandatory. Each month I enter my account info, pay the bill and that’s it. For me the idea that sending a check in the mail is more secure is a false sense of security. Once they receive your check they have your account number anyways.

It’s not like a company takes a sack full of personal checks down to the bank each month and makes a deposit. I would guess a payment check is scanned and recorded electronically. So your account info is in their system anyways.

I like the idea of paying online because you have an electronic receipt the payment was received. An email receipt is evidence. Sticking a check in the mail and hope it gets there in time or at all is not my idea of security. Can’t tell you how many times my neighbors have received my mail or I received theirs. That’s not secure to me at all. I’d rather not have a check disappear in the mail or end up in someone else’s hands. Especially with your checking account number printed along the bottom of the check.
 
1. Consider accepting digital payments/transfers. And the best organizations to begin with would be, in my opinion, the Apple & Goldman Sachs combo -- primarily because of Apple, of course. Your information will be kept private and confidential, and you can trust Apple's payment and processing security.

2. For an extra protective layer, open a second free, no-fee checking account at your current bank or credit union. And use this second checking account as your sole account for electronic payment processing. I don't think it will ever happen, but assume the worst and there is a hack or organizational error and something happens to the funds in this checking account. With this second checking account, you will have contained the damage, and the mess, to the limited amount of funds you put into this second checking account.

3. Mailed checks are not so secure. Yes, they usually get there, and the U.S. Postal Service is excellent. But delivery errors regularly happen. So do processing errors. And your paper checks are subject to theft -- if an identity thief gets their hands on it, it is easy to chemically wash the ink off your check, enter a new payee and amount, and cash that check at a supermarket, payday lender, or unscrupulous money-wiring service. Uncashed bank checks are a favored target for fraudsters, because it is an easy fraud to pull off with a high rate of success.

Bottom line, you may not want Apple or Goldman Sachs to have your "bank account information." Yet every single time you mail a paper check, you are sending out that very banking information "in the clear" through the U.S. mails and through the payment processing vendors who cash/process your checks. The instant you put your paper check in the mailbox, your bank account information is, quite literally, sitting in a think paper envelope, then in the mailbox, then in the mail carrier's truck, etc. etc. No encryption, no security, and out of your hands to who knows where. Ponder it for a moment, and you may come to realize there is a robust argument to be made digital payments using Apple Wallet and Apple Card is more secure than your paper checks.
 
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I will “try” to throw some humor in here and make a suggestion in jest.

Find a buddy who doesn’t mind using electronic payments, etc. and just give them cash for what you owe (maybe toss in a buck or two for troubles) and have them send you an Apple Cash iMessage. Then use your Apple Cash to pay off the card.

Just tryin’ to be helpful :)
 
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