How the hell does this happen

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It is odd how this can occur.

In 2018, I traveled to Brazil and used my Amex card here and there. Mostly, just big name hotels. No problem.

In 2019, I returned to Brazil carrying that same Amex card (which at that time had been deactivated) in my "dummy wallet" with a few other expired cards and a little cash in the event of a robbery. I do that whenever I travel overseas to avoid the inconvenience of having to cancel things from afar. Since it was deactivated, I of course never used it and didn't have my replacement with me on that trip. However, within hours of arriving in Brazil, someone hundreds of miles from where I was started trying to use the card. Found out because Amex thought I was mistakenly trying to use an old, dead card.
 
I use my credit cards for points and cash back (and, yes, I pay them off every month). I use them for almost every transaction I make. If I needed to confirm every transaction, I would go batsh!t crazy. I have two factor authentication on other accounts, but I always feel it would only take someone cloning my phone to make that useless, too.
 
I use my credit cards for points and cash back (and, yes, I pay them off every month). I use them for almost every transaction I make. If I needed to confirm every transaction, I would go batsh!t crazy. I have two factor authentication on other accounts, but I always feel it would only take someone cloning my phone to make that useless, too.

I do the same thing use for every thing. Pay off and go shopping with points.
 
The only thing I shop for with points is FF mile trips. I used to find great deals on Delta to Europe in biz class, but those days are long gone. Now, it's this side of the globe, mostly in coach.

Edit: I just looked at Bonaire. I can fly in main cabin coach for 34,000 +$70 round trip in June from Tuesday to Tuesday.
 
About your last point, it is exactly what I said in the post I replied, you are limited by the lowest security denominator. In Europe it is common to limit the amount on contactless for visa or Mastercard. In the UK it will force you to use chip and pin after too many contactless transactions.

The lowest security denominator is CNP transactions.

We do chip and pin on the debit cards and can do it on the credit ones -- have to for e.g. ATM withdrawals. My CU sends me texts and e-mails on transactions exceeding a threshold I specified, and will block my cards when used overseas (or even out of state in some cases) when we forget to file our travel plans with them. This isn't Wild West here, you know.

Edit: as other have said we use credit cards with "less security" because of the perks and conveniences, and the streamlined fraud resolution process is one of those.

@formernuke's incident is most likely an inside job by somebody temping at national. None of the things you speak of help against inside jobs.
 
The lowest security denominator is CNP transactions.

We do chip and pin on the debit cards and can do it on the credit ones -- have to for e.g. ATM withdrawals. My CU sends me texts and e-mails on transactions exceeding a threshold I specified, and will block my cards when used overseas (or even out of state in some cases) when we forget to file our travel plans with them. This isn't Wild West here, you know.

@formernuke's incident is most likely an inside job by somebody temping at national. None of the things you speak of help against inside jobs.
Are you saying that requiring 2FA wouldn’t help?
 
Are you saying that requiring 2FA wouldn’t help?

Depends on merchant's setup. All the bank really needs is card number and transaction amount, whatever extra checking's involved may be offloaded to the merchant, or to Ragnesh in Bangalore, or built into bank's protocols.
 
https://www.shearwater.com/products/teric/

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