this post was submitted on 27 Sep 2023
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So I've been running self-hosted email using Mailu for a couple of months (after migrating out of Google Workspace). Today it turned that although my server seems to be capable of sending and receiving emails, it also seems to be used by spammers. I've stumbled upon this accidentally by looking through logs. This seems to have been going on for all this time (first "unknown" access happened just a couple of hours after I've set everything up).

While browsing the logs there were just so many crazy things happening - the incoming connections were coming through some kind of proxy built-in to Mailu, so I couldn't even figure out what was their source IP. I have no idea why they could send emails without authorization - the server was not a relay. Every spammy email also got maximum spam score - which is great - but not very useful since SMTP agent ignored it and proceeded to send it out. Debugging was difficult because every service was running in a different container and they were all hooked up in a way that involved (in addition to the already mentioned proxy) bridges, virtual ethernet interfaces and a jungle of iptables-based NAT that was actually nft under the hood. Nothing in this architecture was actually documented anywhere, no network diagrams or anything - everything has to be inferred from netfilter rulesets. For some reason "docker compose" left some configuration mess during the "down" step and I couldn't "docker compose up" afterwards. This means that every change in configuration required a full OS reboot to be applied. Finally, the server kept retrying to send the spammy emails for hours so even after (hypothetically) fixing all the configuration issues, it would still be impossible to tell whether they really were fixed because the spammy emails that were submitted before the fix already got into the retry loop.

I have worked on obfuscation technologies and I'm honestly impressed by the state of email servers. I have temporarily moved back to Google Workspace but I'm still on the lookout for alternatives.

Do you know of any email server that could be described as simple? Ideally a single binary with sane defaults, similarly to what dnsmasq is for DNS+DHCP?

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[–] vzq@lemmy.blahaj.zone 61 points 1 year ago (1 children)

After spending a considerable amount of time on it, I have come to the conclusion that there is no completely reliable way to send email without relying on a third party that is considered to have a “good reputation”.

Your set up might work right now, but tomorrow everyone on the internet could stop accepting your mail without explanation and without recourse.

If you own your own IP range, things look a bit brighter, but if you’re dependent on residential and housing provider addresses, you’re boned.

[–] Shdwdrgn@mander.xyz 14 points 1 year ago (2 children)

I agree that a static IP address is an absolute requirement for a mail server to send messages these days. You also need a host of checks in place like SPF, DKIM, and DMARC, along with a strong set of blocklists and spam filters. My own setup includes dual ISP connections from two different providers, and even with all that in place, Microsoft has always been a thorn. They will block me for no apparent reason, their own tools don't even show any detected spam activity, and sometimes they don't even block the same IP address (or provider) that my emails were sent from. Every other spam service on the planet behaves in a rational way, but of course Microsoft has made a point of locking in so many businesses to their own spam-ridden service that you simply can't run a mail server any more without being able to talk to them.

Overall, yeah it can be a pain to run your own mail server. I can't imagine trying to use a pre-built mail server and expect it to run, there's so much that you have to configure to each specific setup. It's not like a web server where you load up a docker container and it just works.

[–] vzq@lemmy.blahaj.zone 12 points 1 year ago (4 children)

I agree that a static IP address is an absolute requirement for a mail server to send messages these days.

No no, I don't mean a static IP address. I mean an IP block allocation. I mean an Autonomous System (AS). I mean actually owning your IP ranges.

Static addresses are subject to the whims of the provider, and even when they are actually static, much of the "reputation accounting" is influenced by the other users of your block. The only way you can guarantee the kind of continuity needed is by owning the entire IP allocation block.

It's not a game for the little guys.

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[–] witten@lemmy.world 4 points 1 year ago (1 children)

I've had similar experiences trying to send mail to Microsoft-hosted email addresses. My current "solution" is to send all outgoing mail directly from my VPS-hosted Mailu server... EXCEPT for Microsoft-destined mail. For those messages, they get transparently relayed from Postfix to a third-party email sending service that Microsoft apparently trusts.

The upshot is I can still use my own Postfix daemon for all mail sent to sane (non-Microsoft) providers.

[–] Chobbes@lemmy.world 2 points 1 year ago (4 children)

I've never heard of anybody relaying just the Microsoft e-mails, but that's a really funny spiteful solution.

Lately I've been able to send to outlook just fine (maybe it's just dumb luck, who knows). I think I had troubles initially because they're really picky about rDNS matching the MX exactly. I also signed up for SNDS just in case, but I don't know if they factor that in...

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[–] daFRAKKINpope@lemmy.world 26 points 1 year ago (2 children)

ProtonMail. 100%.

I set up custom DNS and catchall so yourcompanyname@saltycowboy.org is really how I filter spam.

Please note, saltycowboy.org isn't really my domain.

[–] __ghost__@lemmy.ml 9 points 1 year ago

So you're saying it's available? 👀

[–] Unforeseen@sh.itjust.works 2 points 1 year ago

I've also done the same, it's been great.

[–] slander@lemm.ee 19 points 1 year ago (1 children)

unless you realllllly enjoy self hosting your email, IMO it’s just not worth it anymore with the state of things. I use Fastmail and could not be happier.

[–] specseaweed@lemmy.world 3 points 1 year ago

Same here. Gave up and went fastmail. Love em.

[–] Cosmos7349@lemmy.world 15 points 1 year ago (2 children)

I use fastmail, and I enjoy it a lot. Their masked email is very nice as well, and integrates with bitwarden. So quite convenient to use my personal domain for stuff where my identity matters, and use masked @fastmail addresses for more disposable stuff.

The only thing that ticks me a tiny bit is that their mobile app doesn't have offline mode; but you can use imap client or w/e, so it's not too much of an issue.

Also hear good things about protonmail; I would consider it if I didn't already use/trust fastmail.

[–] fraydabson@sopuli.xyz 6 points 1 year ago

Another vote for Fastmail. In my recent effort to degoogle I switched to Fastmail and I love it.

[–] BitSound@lemmy.world 5 points 1 year ago

For mobile with fastmail, I use fairemail. Works great with it, and provides a nice merged view with my non-fastmail work emails.

im an old school email admin. i gave up on my personal exchange box for protonmail years ago.. multiple domains, lots of dns nonsense on my part. zero problems.

i highly recommend them.

[–] KairuByte@lemmy.dbzer0.com 7 points 1 year ago (5 children)

https://mxroute.com/ is what I went with. They have a $99 lifetime plan. Semi limited, but worth it imho.

[–] RegalPotoo@lemmy.world 2 points 1 year ago

I'd be super cautious about relying on any company that even offers a "lifetime" plan.

Offers like that are tools to raise cash - take money now for a service that you will provide people in the future. They tend to get used in one of two situations:

  • We need to raise money for investment in upgrades, so take the equivalent of ~2-3 years subscription from people up front, and count on the investment bringing in enough new customers paying regular rates that you can cover the cost of having the lifetime customers out of revenue
  • We need cash now or we aren't going to be able to pay salaries, and it won't matter that we've screwed our customers if we are bankrupt

Even in the best case, it'd be much simpler to raise cash through usual investment mechanisms, so you do have to wonder how viable their business strategy is if they can't get money that way

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[–] Decronym@lemmy.decronym.xyz 5 points 1 year ago* (last edited 5 months ago)

Acronyms, initialisms, abbreviations, contractions, and other phrases which expand to something larger, that I've seen in this thread:

Fewer Letters More Letters
DNS Domain Name Service/System
Git Popular version control system, primarily for code
IMAP Internet Message Access Protocol for email
IP Internet Protocol
SMTP Simple Mail Transfer Protocol
SSL Secure Sockets Layer, for transparent encryption
TLS Transport Layer Security, supersedes SSL
VPN Virtual Private Network
VPS Virtual Private Server (opposed to shared hosting)

8 acronyms in this thread; the most compressed thread commented on today has 3 acronyms.

[Thread #169 for this sub, first seen 27th Sep 2023, 14:35] [FAQ] [Full list] [Contact] [Source code]

[–] ChojinDSL@discuss.tchncs.de 5 points 1 year ago

I use mailcow for self hosting.

[–] aard@kyu.de 5 points 1 year ago

Nowadays I'd recommend a simple postfix + dovecot setup. If you care about a web-UI and possibly some groupware functions put SOGo on top.

[–] Rearsays@lemmy.ml 4 points 1 year ago (3 children)

Just switch to mail in a box.

[–] RootBeerGuy@discuss.tchncs.de 3 points 1 year ago

Step 1: cut a hole in the box

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[–] eros@lemmy.world 4 points 1 year ago

I found myself in a similar situation last year. MXRoute's lifetime plan works well for those domains that just need basic email and not a lot of storage.

[–] cooopsspace@infosec.pub 4 points 1 year ago

Fasmail + domain

[–] benmi@lm.inu.is 4 points 1 year ago (4 children)

I have used https://migadu.com/ for over a year now with no problems. Very happy with them. Setup is well documented.

[–] NightAuthor@lemmy.world 2 points 1 year ago

Most reasonable pricing I’ve seen for a family use case.

[–] otl@lemmy.sdf.org 2 points 1 year ago

This was the provider I went with after self-hosting my mail for 7+ years on an OpenBSD VPS. I feel like Migadu is an honest and good-value service.

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[–] emhl@feddit.de 4 points 1 year ago
[–] techgearwhips@lemmy.world 3 points 1 year ago* (last edited 1 year ago)

Protonmail. That's what I use connected to my own domain.

[–] Appoxo@lemmy.dbzer0.com 3 points 1 year ago (1 children)

Personally using Ionos.
Not bad experiences so far but you need to watch out at times and check your invoices.

[–] stown@lemmy.world 2 points 1 year ago

Same, IONOS is cheap and I had no issues when requesting they open port 25 for my mail relay server.

[–] beirdobaggins@lemmy.world 3 points 1 year ago (1 children)

Moved from a junky setup where I was forwarding my domain mail to gmail. And sending mail through gmail using the smtp server provided by my web host.

I was having too many issues.

I switched to fastmail. It is quite good. And you can get some free basic web hosting included with your paid service.

[–] ssdfsdf3488sd@lemmy.world 2 points 1 year ago

This is what I did too, after self hosting and self hosting anonaddy for a while. I really like how it integrates into bitwarden to give me most of what I liked about anonaddy as an included thing. I also did it ofr the same reason. Too many Eh holes out there that just want to bang on the mail server all day.

I ended up on purelymail.com for my machine sending email (it's dirt cheap I think I will be under their minmimum and it will cost something like 10 dollars a year for unlimited unique email addresses for my services)..

[–] Chobbes@lemmy.world 3 points 1 year ago

Oh no! I'm sad to see that you've run into troubles :(.

There are other "fully put together" solutions like mailinabox and mailcow, that could be worth looking into for you. I haven't used them personally, but you might find them worth looking into. I'd never heard of mailu before, actually.

Totally understand the desire to just move to a hosted solution after running into these problems, but even if you do that I think you should keep running a mail server in the back of your mind for the future


you've already learned a lot about it I'm sure, and maybe with a bit more experience you'll be ready to tackle it again :).

I don't actually use any of the fully assembled solutions like mailinabox, and I wonder if in the future it might be a good idea to try configuring everything manually. You already have some familiarity with how mail works at this point, and having more control over the setup and how everything fits together might actually work out for you. Personally I'm running an OpenSMTPD + Dovecot mailserver and having a great time. I'd recommend it.

https://poolp.org/posts/2019-09-14/setting-up-a-mail-server-with-opensmtpd-dovecot-and-rspamd/

Either way, I think you should keep using a custom domain for e-mail because then you have options in the future :).

[–] ninjan@lemmy.mildgrim.com 3 points 1 year ago (1 children)

I use iRedMail but would I call it simple? No. Mail is such old tech that simple really isn't the word for it. Archaic, ancient and dying fits better. But it will take decades more to actually die. iRedMail is available as a single container, which isn't correct from a container perspective but makes everything a lot easier in my opinion. Of the various solutions I've tried it's the one closest to the goal of "It just works". The biggest downside is the manual steps often needed to upgrade version. Not to time consuming but far from "It just works".

[–] elbarto777@lemmy.world 5 points 1 year ago (1 children)

Why should email die as opposed to evolve?

[–] ninjan@lemmy.mildgrim.com 5 points 1 year ago (2 children)

Eh, I guess it's a Ship of Theseus kind of thing. So much in the core is roten that if we change it you could argue it will be something different.

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[–] markstos@lemmy.world 2 points 5 months ago

I hosted email professionally for over a decade... and I can't recommend getting back into the business. At that time we were using Qmail, although I also have experience managing Exim and Postfix. About 90% of incoming email remains spam.

For outgoing email for things like server cron mail, a stub service like msmtpdcan be used to receive local mail and forward it to to a local service.

To receive and host email, Fastmail is good.

[–] Voroxpete@sh.itjust.works 2 points 1 year ago

Throwing my hat in for Protonmail.

[–] rmdes@lemmy.world 2 points 1 year ago
[–] robert@lemm.ee 2 points 1 year ago* (last edited 1 year ago) (1 children)

I vote for maddy, but one important note for my setup: my family uses always-on VPN, so i only open port 25 for the world. Imap can be accessed only from vpn. In such case server can't be used as relay from internet. Maybe try that way?

[–] Socket462@feddit.it 2 points 1 year ago (1 children)

I am not saying your server is not secure, but just fencing off IMAP from the web is not enough to limit spammers from relaying mail through your server. They usually exploit a misconfigured SMTP server, which does run on port 25 (plain or start TLS mode)

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[–] ikidd@lemmy.world 2 points 1 year ago

Mailcow dockerized.

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