I know all email services are technically "encrypted" but you know what I mean, the privacy-centric email services like Protonmail and Tutanota. I have done a test-run of both and found myself struggling to fully move over since so much of my life is already connected to my current emails. However, I don't like the fact my current emails have a lot of identifying information.

Has anyone here fully moved over to a service like that and has it hindered anything at all? Like applying for things.

I've moved entirely to Proton for work (self employed). No regrets (and no spam).

Actually almost none are. Yahoo, Gmail, Hotmail (whoever still uses that), etc. are all unencrypted, or at the bare minimum encrypted-at-rest, but that means the company can still just read all of your shit since they have the keys, be it for surveillance purposes, or just a malicious employee trying to sell/dox info about a specific customer (like some Sony employees did to some livestreamer recently). I've been using various services like this for about a decade at this point. I used to have a ProtonMail Visionary plan, but in recent years I was using Tutanota + AnonAddy. AnonAddy offers similar functionality to ProtonMail's Proton Pass alias feature, where you can create a unique email address for a specific service and have it forwarded to your real email. AnonAddy offers the ability to encrypt the emails with PGP so that your email provider cannot read them (though AnonAddy can see the contents, unless it was encrypted before being sent to AnonAddy, if you're concerned about that).

Overall you can't go wrong with either combination (ProtonMail + Proton Pass' alias feature or Tutanota + AnonAddy). In the event of a site you use is breached, if you use unique aliases for each site the chances of attackers attempting to get into other accounts you own based on your login info (like the email) from said breach drops to basically zero. That alone is almost entirely worth it to me.

However, even if you use ProtonMail, but still message your friends/family back on Yahoo/Gmail/whatever, then all end-to-end encryption is basically thrown out the window as Yahoo/Gmail/etc don't support that, so if your friend/family member quotes your email in their reply, or receives an email from you, then Gmail and such can see those emails of yours too.

In addition to all of this I recommend using something KeePassXC to generate unique passwords and store them securely offline. It's FOSS so no subscription or always-online bullshit.

One issue that one may encounter relates to electronic mail messages not even reaching the inbox of the intended recipient(s). For a number of web sites, I have had two-factor authentication messages fail to be delivered (and this has not changed for the better in years of intermittent re-tries), thus temporarily locking me out of the affected accounts for those sites. Due to the previously mentioned problem, I have had no choice but to revert the associated electronic mail address to that of one of the 'standard' providers. Some organizations are much more lenient than others, but, one must accept the possibility that fallbacks may be necessary as a select subset will outright block mail from privacy-focused and/or foreign-based mail providers.

It is unfortunate that the group of trusted electronic mail providers is rather exclusive. From my years of reading (but, not first-hand experience), unless one has had a well-established (and reputable) domain (and reasonable internet service provider whom permits certain traffic), in this day and age, it can be difficult to host a personal mail server without external parties rejecting incoming mail from it. This last paragraph is probably not relevant, but, I am simply lamenting the fact that the 'clear web' is not nearly as open and inclusive as it could have been.

Some sites (related to: state and federal government, health care, insurance) require this; it is not by choice. They offer no other alternative.

I use a mix of mail providers scattered across the globe, and this issue, in my direct experience, has been frustratingly common.

Not sure which country you're in (edit: just saw your mini profile here in this thread says US), but in the US I have ProtonMail and Tutanota/AnonAddy emails used for various services such as healthcare stuff, driver's license, library, etc. and haven't run into any issues with them and my email, though pretty much all of those govt services I have accounts for don't offer any 2FA at all (typical govt incompetence lol)

Thanks for the replies.

I've heard conflicting opinions about certain websites refusing to send emails to proton/tuta services. I suppose I can always keep my primary email for those things.

Email is always unencrypted, it was not designed for private communication.

What you can encrypt is the text of the message itself and the subject string. But meta-data ( a lot of identifying information ) will remain plain-text.

To use that kind of encryption you should exchange public keys with each of your contacts. Actually, it is a lot of hassle. If person or organization does not use email encryption ( the vast majority don't ), your communication will be unencrypted.

What Protonmail and Tutanota provide, is an encrypted messenger on top of their email service. To use this messenger, both parties should have an account on their respective service. If you communicate with another email provider ( even between Protonmail and Tutanota ), the message will be sent as a plain-text.

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Therefore, if you want a really private communication, you should choose end-to-end encrypted messenger instead of email.

If you simply want to reduce an amount of your data, leaking from general-purpose email:

1. Choose an email provider, which you can trust ( avoid corporations and ISPs ) Read their privacy policy with attention.
2. Use standard imap / smtp client instead of web-interface or provider's app.
3. Delete messages from server after reading. Store copies of important messages offline. & I've fully moved to email service, provided by a small local company. I don't have problems with any websites.

full disclosure: it's something I could do more but have never practiced. You'd think it's easier to use only one email, but I admit having three burner phones and encrypted accounts sounds alluring.

No, but I have considered moving to a self-hosted mail server or another service entirely.

We tried tuta, and when they started arm-twisting us to pay extra for more features we didn't need, hard pass, then followed by making it hard to even log in, by saying over and over: server connection lost, try again, that was Sayonara time for us.

I use protonmail for services I care about (Steam, GOG, itch.io) and outlook as a burner for those I don't (Epic, Microsoft). And for privacy sake, never EVER link your account in galaxy to other platforms, or for that matter, between any platform, as then when the platform is data-leaked than the hackers know about all your accounts not just the one.

I have been using a self-hosted e-mail server for more than a decade, and have been encrypting my e-mails for even longer than that.

Two important things to keep in mind:
- Encryption can only work when it is supported by both ends of the e-mail exchange;
- Encryption can be done with any e-mail provider, using a mail user agent supporting encryption (the most popular would be Thunderbird, here I use Claws Mail).

In the end it does not change a single thing with subscriptions or other kind of accounts, because in such exchanges the e-mails are not encrypted. If people got deliverability problems after switching to a service with encryption support, this is not due to the encryption itself.

With this in mind, what would the primary value of these services be then? I liked not needing to give them any details about myself outside of payment details if I wanted to subscribe to more features, maybe that's worth something. Though, I noticed Tuta didn't let me delete payment information, and Proton made it awkward to remove payment information also.