What's the best approach to email today?

Never use email for anything requiring privacy. Email is for paper trails. That's it. Sometimes for you, often times against you. It doesn't matter if you use Proton, Tutanota, FastMail, Gmail etc. The other person probably isn't and they + their provider will share anything you send so be on your best behavior.

Correct answer
Certified email would solve this, if it was possible to self host it.
Unfortunately running it requires government approval and the resulting emails are legally binding, so I assume hosts will have to go through all kinds of security controls and audits.
- I think that misses the point. Emails are kind of antithetical to transient and private communications. People are much better off using a generally respectful service that doesn't scan their mail for normal use and turn to better tools like Signal (which require both receivers to use an agreed-upon/enforced and privacy-focused infrastructure) or any other messenger with disappearing chats that limits metadata retention.
Both hands in favor!
- What is the sound of one hand in favor?

https://www.privacyguides.org/en/email/

Normal email is unencrypted when it's on the wire in transit. (Nowadays they use SSL between servers, but it's totally readable by every server in your pathway. Which isn't much better ). The best you can hope for email is to encrypt it and store it at rest once it arrives at the server. If you self host the server you could have one way encryption enabled. If you don't want to self host the privacy guide options are pretty good.

Don't have any conversations via email if you can avoid it. Prefer end-to-end encrypted platforms like signal instead

These days almost every mail server will send mail over tls, but it’s not a guarantee which is a little unfortunate. Like you say there’s always privacy concerns with email, unfortunately.
I think in terms of privacy it really depends what you care about and what you’re using it for. If you care about Google reading your inbox, then self hosting can in theory help (at least for emails where the other party isn’t on Google or whatever)… Personally I like the idea of Google not knowing every company that I have an account with and everything I order online, which is information that’s definitely in your inbox. If you care about obscuring who you are to services that you sign up for with email, then arguably self hosting is not ideal because you’ll be the only one using that domain for email, and you might be better obscuring yourself through something like Apple’s “hide my email” service (which of course means you trust Apple to see those emails instead).
If you have more serious concerns and are having conversations that you don’t want anybody other than the recipient to know about email is probably the wrong choice for that conversation, but PGP is a decent option in these cases, albeit too clunky for most people. You may consider other services like protonmail or tutanota, but there are concerns with these services as well (eg, protonmail gets some flack for not encrypting metadata like message subjects, which is a big deal) and again there aren’t necessarily good guarantees for anybody you’re talking to on gmail or whatever.
Personally I like self hosting my email because of the flexibility that it offers and the price. It’s nice to be able to have as many email accounts as I want and it’s cheap to host, and I enjoyed learning about it and setting it up. My personal inbox is out of the hands of giants, but obviously if I’m emailing normal people it’s probably going to be available in the clear to Google or Microsoft (which is likely the case regardless of your solution). That’s not ideal, but it’s the reality right now with email. I kind of think of email more like a Twitter account or something at this point. It’s a semi-public way for random people to get in touch with you and a lot of conversations might be kind of explicitly public like on mailing lists, or something more akin to talking to a colleague in a public space — not super private, but a convenience, I guess?
I’d still recommend that people do try to self host their email if they’re thinking about this. Independent mail servers seem like a healthy thing for the web and learning more about it will give you a better sense of how secure / private your emails really are. Things like protonmail seem to have some advantages, but I also get some weird vibes from them and I’m not sure how much of a privacy increase they really give if you aren’t talking to other protonmail users and stuff anyway.

I use Protonmail

Proton mail with your own domain + catchall.
Has quite a few benefits over other options.

A privacy email provider and email aliases for everything you sign up for.

Email Providers

Protonmail

Tutanota

Email Alias Providers

Simplelogin

addy

Proton pass does e-mail aliases if you pay up for the high tier subscription
- Which is through SimpleLogin, which Proton bought.
- Theres plenty of good reason to keep your alias provider separate from your email provider.
  The first being you can lift and shift to another email provider very easily.
  Secondly if something happens to your account you don't lose the lot.
  Thirdly, just get a domain with alias provider and it matters not what email provider you use ever.
- They do but it's a limited kind of alias. You can't set up reverse-aliases (you send first) for example which the regular SimpleLogin can.
- But its though SimpleLogin, not ProtonMail itself.
I am new to the alias world so I've a question. How can I be sure that an alias provider doesn't have access to my emails when they are forwarded?
- Unfortunately there is no way, it requires trust. Just like you need to trust your email provider to not have access to your emails.

Privacy is a spectrum…. A journey not a destination…

Yes self hosted is the most private to a point… ie you are responsible life configuration and security, and even good admins screw it up.

Proton is good as far as we trust them, how paranoid are you do you trust them a nS their audits?

Sigh. It is hard. Email isn’t that secure. Treat as though it will be and can be exhibit A in court…

Use signal for anything that needs to stay “that” private

Ymmv

There isn't really privacy in email unless all recipients are encrypting the email body itself. Email leaks a lot of metadata even with GPG use, and it's typically stored at rest in plain text.

There are tweaks you can do that will accept the unencrypted email, then immediately encrypt the message with your key so only you can read it. Then it would be safer at rest, but less convenient. It really depends on your threat model.

I own a custom domain and actually use Tutanota as my host. Self hosting is a nightmare and easy to fuck up, which leads to your emails getting sent to spam or just not receiving. I use custom domain support in Tutanota that costs me $12/yr (2 custom domains) and my domain is $15/yr. Since custom domains stick out like a sore thumb, if I need privacy then I will use AnonAddy to forward to my email with an anonymous forwarder.

Like 99.9% of my emails aren't encrypted but that's not the point. Tutanota removes a lot of the privacy leaks via metadata and has privacy protection measures by default like disabling images from automatically loading. Also it's calendar/contacts/email all rolled into one and everything is e2ee. Not to mention, unlike ProtonMail, they have their own push service that works on DeGoogled Android and can be installed from fdroid.

this is a very sensible alternative to actually going all-in on self-hosting mail, which is a total pain in the ass.
Oh wow. Maybe I will migrate to Tutanota from Proton then. That price, function, and dedication to privacy sounds quite attractive to me.
- I'll just say though, the client is kind of rough and may be missing a lot of features you're used to.

I use fastmail.com to generate e-mail aliases. Creation is rate limited, but they are virtually unlimited; I have 500+ and counting. Aliases are randomly generated as wordone.wordtwo1234@fastmail.com, so they aren't identifiable to your account.

Anonaddy/Addy.io to create aliases, then PGP encrypt it before forwarding to my Google mailbox.

I also use Proton but considering ditching it in favor of Anonaddy.

Self-hosting email is a major pain in the ass. Good luck avoiding spam filters.

FWIW, self hosting email is such a pain in the arse to get to a working state, I'll join the rest of the comments and say proton

I think if somebody does want to self host email we really shouldn’t discourage them. It’s a bit more complicated than somebody might expect going in, but you really don’t need that much to get everything in a working state, and it’s something that will get better the more people do it because more people will write tools and guides and make saner defaults, and large mail companies will have to take independent mail servers more seriously.
Totally cool if it isn’t for you of course, and people should be aware that it’s important to set up rDNS, dkim, DMARC, and SPF (most of these are just simple DNS entries that you need that help with interacting with other mail servers), because otherwise their emails are going to be sent to the spam zone… But these are not insurmountable obstacles if you really do want to do it!
- No you're right, I shouldn't discourage, just wanted to warn it's not the same as most other self hosting projects, where often you just need to spin up a docker container.
  FWIW hasn't DNSSEC/DANE been added to the prerequisites these days or is that still optional?

If you want to self host, I recommend mailcow. It is not that hard to install and if you follow the instructions you'll have a working solution whose mails are not considered spam by every other sane server. Sadly, some operate with whitelists.

- 6GB of RAM is for up to 8 concurrent users.

People here seem to think that email alias providers are more secure then a custom domain. I would argue they are the same.

If someone is going through the trouble to find you, the alias provider will give up your payment information and your real email address.

A custom domain will give up your registered information.

If you want a truly anonymous email, don't have it funnel to your personal / main account.

I'm using Skiff Mail with two custom domains.

Tutanota with own catch all domain

Do not use proton, get yourself a domain and then use something like Migadu to host it for you on that domain. Then you can also use anonaddy to add anonymous addresses where needed.

self host. Don't trust random "privacy" companies

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