Help me understand simplelogin and why so many recommend it. The tradeoffs don't make sense to me.

You are sending all plain text email transmissions in to a central company who then forwards them on.

Sure they are open source, say they don't keep records and delete but there is no way to know or not if they really are deleting after forwarding.

I guess it's the same tradeoff we make with VPN providers but this seems worse to me for some reason 🤷‍♂️

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If you are not self-hosting the simplelogin stack than you have to trust them just like with every email provider. It’s a downside of e-mail as a protocol, that it is not easy to self host and the provider gets your plain text mails.

If you can trust simplelogin than you gain a lot of advantages because you never have to give out your real email address.

If a burner address gets leaked you can simply disable it and know which site leaked it because you use a different address for every site.

Also you cannot be tracked across sites by your email address as a unique identifier.