I literally couldn't apply for an American Express card about 15 years ago because my (ISP) email address was too long. I wonder why they chose to restrict it rather than go with the standard email max length; they had to put effort in to pointlessly restrict new signups. Odd.

Back in '99 or so, there was a company called Halibut Stuff selling T-shirts at Defcon (and presumably other events) that included a free email redirect service with purchase of a shirt.

So I got a shirt that said "[email protected]"

Not too much later, I ended up working in software validation, and I broke so many login forms with that perfectly-valid address, I lost count.

Since then, Halibut Stuff dissolved and the forwarding service is long gone. If some HN reader wanted to set up a Mailinator-like service that generates absurd-yet-RFC-compliant email addresses for such testing, I think there might be a market.

Like anyone would actually use such a testing service.

Until a few years ago it was fairly commonplace for sites to reject my perfectly valid addresses just because they had more than one period (i.e., a subdomain) or in one case, ended in the .us TLD.

Likely because of integration with legacy tech.

I remember when their max password length was 8 characters. It blew my mind that a (effectively) bank had such terrible requirements. At least they fixed that

The 8-character limit was probably because the web site was just a fancy front-end to some decades-old mainframe system. You'd be surprised the age of technology and software big banks rely on. They tend not to fuck with a working system, partly because their reputation and millions or billions of dollars are on the line, but also because no manager wants to be the reason for a critical outage.