A point can be made here for email providers that also provide aliasing services such as Protonmail/SimpleLogin: Since they’re the same entity, using an aliasing service requires no additional trust.
Problem is that this domain (whether it includes your real name or not) is still related to your person as you are the sole user.
If you created accounts at Google, Amazon and Facebook using a schema of servicename@thisspam.com, don’t you think they’d be able to tell it’s the same person who created those accounts?
With the likes of google.quothfaaoa@aliassingservice.com, amazon.qwrlaklfas9@aliassingservice.com and facebook.1afglasdah@aliassingservice.com, that identification vector is simply ruled out.
This is going to be controversial, but if I was a user of these three scummy sites what you say above isn’t the hill I’m willing to die on or care about.
However I have half a dozen domains, I could quite easily add one or two more for dumb shit like this if I wanted to.
There is also Firefox relay which gives you 5 email aliases. I have found that some services such as discord do not accept addy or simplelogin domains but they accept firefox relay domain which is mozmail.com if I am not mistaken
self hosting email is not worth it unless you are Edward Snowden or some whistleblower trying to hide from the biggest government agencies in the world
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.
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.
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.
I have looked at it and its system requirements are just insane. No way it would run on my cheap 1 GB VPS. I use a script for setting everything up, but less because I want to (I was warned about complications) and more because I cannot afford a second subscription.
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.
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.
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.
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?
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.
Yeah, this is very fair! I just wanted to also provide the other perspective. Self hosting e-mail is very doable, and I think there are some things like mailcow / mail-in-a-box that make setting up the software on the server a lot easier (I haven’t used these, but I’ve heard good things)… But you’re probably still going to have to double check your rDNS and make sure to add the appropriate DNS entries… And you might not even realize that you have to do that, and then you’re like “why the hell can’t I send e-mail to anybody”, and it’s not the easiest thing to debug (especially if you haven’t set up DMARC entries for getting reports from other mail servers). Plus… If you get the DNS entries wrong it can be a pain to wait for the TTL to expire to make changes. The setup definitely isn’t without its headaches and hassles, but it’s not impossible and once it’s good to go you probably won’t have to change anything.
FWIW hasn’t DNSSEC/DANE been added to the prerequisites these days or is that still optional?
This is currently optional afaik. I believe you can use this to establish that your e-mail server accepts TLS so other mail servers can know not to downgrade to an unencrypted connection. Admittedly, I’m not super up to date on this, and I’m slightly confused about the differences between MTA-STS and DANE. Also fwiw, I think both of these solutions mainly impact receiving mail, and shouldn’t make much of a difference if any for you sending mail to the big providers.
Okay, so I did some research to confirm my previous understanding and for the sake of completeness I just wanted to throw this information into this thread… Neither DNSSEC/DANE nor MTA-STS is required. AFAIK none of the huge e-mail providers like Gmail, Outlook, or iCloud implement DNSSEC/DANE, but protonmail and tutanota both do. Of those everybody implements MTA-STS, except for iCloud.
In the case of e-mail both of these aim to alleviate a big security flaw in e-mail, which is that when Alice is trying to send you an e-mail, Alice’s mail server has no clue whether or not your e-mail server supports TLS (e-mail is older than TLS, so it’s bolted on in an opportunistic fashion)… As a result if somebody can get in the middle of Alice’s mail server and your mail server they can say “hey, I don’t support TLS”, and then Alice’s mail server will just say “okay, fine, here’s the e-mail unencrypted”. Obviously such a downgrade attack is BAD, so DNSSEC/DANE and MTA-STS are attempts to prevent this from happening.
DNSSEC/DANE solves this problem because it guarantees that DNS records are legitimate and it can guarantee whether or not a DNS record that says “hey the mailserver supports TLS” does or doesn’t exist. The disadvantage of this is just that it relies on DNSSEC, which has its own caveats.
MTA-STS attempts to mitigate the problem… With MTA-STS you add some DNS records that say “hey, look up the MTA-STS policy from this HTTPS server”, and the HTTPS server provides a file that says whether or not the mail server requires TLS connections to prevent downgrades. This always bothered me, though, because if somebody can attack DNS this arguably gives you very little… And if somebody is in the position to block HTTPS traffic they can prevent the policy from being fetched as well. Theoretically this doesn’t provide much of a guarantee, but I guess in practice it’s probably a decent mitigation because if a policy has been fetched before there will be a cached version available, so you’d need a sustained or well-timed attack to break MTA-STS, and on the plus side they can’t generate a bogus policy file to disable TLS connections to the mail server unless they can get a valid TLS certificate for your domain.
Either way, both of these things are pretty much entirely about receiving e-mail, and aren’t spam mitigation measures, so they shouldn’t have anything to do with your ability to send e-mail (which is the harder part). It matters for sending in the sense that you don’t want e-mail that you send to other mail servers to get downgraded from TLS when it shouldn’t either, which means your mail server should validate MTA-STS + DNSSEC/DANE for mail servers that you are sending mail to. Ideally you would set up DNSSEC/DANE and MTA-STS in order to prevent this class of attacks on your personal e-mail, though it’s not strictly necessary. MTA-STS is pretty trivial to set up as long as you already have an HTTP server on hand to serve up the policy file (which you probably do). DNSSEC may be a heavier ask for people depending on TLD support, registrar support, nameserver support, and software support (a lot of the DNSSEC signing software coughldnscough seems to choke on certain RRs -_-), but this may be easy for many people to implement.
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.
Add comment