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Maddy: Composable all-in-one mail server

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Re: Maddy: Composable all-in-one mail server

#71

Post by dhess »

g_p wrote: post #58
n3storm wrote: post #15

Earlier quoted context omitted.

Your mail will go to Spam too with Maddy, this is not about the MTA.

One "weird trick" I discovered with deliverability was that plaintext email from my server was rejected, but HTML email from it was accepted. For anyone with deliverability issues and mail going to spam, it might be worth trying this out (after you have sorted all the usual points like DKIM, SPF, PTR record etc.) - this obviously only helps if your IP is clean. I was surprised though, and only discovered it by accide…

As someone who has run his own mail servers since 2000, and still gets his email delivered to people's spam folders (even when I've emailed them in the past, or simply replied to their original message), this is very interesting, as I always enable plaintext outbound email.

I'll have to give this a try. Thanks for the tip!

Re: Maddy: Composable all-in-one mail server

#72

Post by viraptor »

n3storm wrote: post #55
reitanuki wrote: post #37

Earlier quoted context omitted.

This is not (always) true. Maddy comes with a lot of the 'good stuff' like DKIM and DMARC ready to be used, whereas setting that up yourself with Postfix was a pain (from my experience a few years ago) and probably meant you didn't bother. I've had better deliverability, especially to Gmail and Microsoft, since using Maddy, probably for this reason. Now, of course, I must admit that self-hosted e-mail seems like it w…

So you agree is not about the software but you did not implement best practices with Postfix. Also, whenever you give an address to someone else, family or friend, risk of going to spam increases. Links or src in emails without https, higher risk, Does Maudy prevent you from doing that?

If one software makes best practices easy to implement and another makes them hard, it still is about software. Not entirely, but it's important.

Re: Maddy: Composable all-in-one mail server

#73

Post by foxcpp »

Firerouge wrote: post #20

Configuration and setup wise, this looks somewhat simpler to setup than the comparable mailcow-dockerized. https://mailcow.github.io/mailcow-dockerized-docs/i_u_m_inst... I wonder how it compares in multi account management and spam, phishing, & virus blocking, is it extensible?

Spam, phishing, virus blocking - no builtin measures. It is easy to integrate rspamd (literally adding one line into config). ClamAV can be used via clamav-milter though some configuration is needed - no direct & easy integration for now.

maddy implements de-facto standard milter protocol so it is possible to use any third-party filtering software supporting it.

Re: Maddy: Composable all-in-one mail server

#74

Post by g_p »

dhess wrote: post #71
g_p wrote: post #58

Earlier quoted context omitted.

One "weird trick" I discovered with deliverability was that plaintext email from my server was rejected, but HTML email from it was accepted. For anyone with deliverability issues and mail going to spam, it might be worth trying this out (after you have sorted all the usual points like DKIM, SPF, PTR record etc.) - this obviously only helps if your IP is clean. I was surprised though, and only discovered it by accide…

As someone who has run his own mail servers since 2000, and still gets his email delivered to people's spam folders (even when I've emailed them in the past, or simply replied to their original message), this is very interesting, as I always enable plaintext outbound email. I'll have to give this a try. Thanks for the tip!

Your symptoms sound exactly like the issues I was having - everything was "right" (in theory) - emails were leaving on the right IPv4, that had the correct PTR, etc etc. I just couldn't figure out what was wrong.

It was the same issue - even replies to existing threads had the issue. What got me looking into it more closely was that I had no issues delivering to G Suite tenants; it was only issues with 365 tenants.

I wonder if there's a non-trivial correlation between people choosing to genuinely self-host their own mail, and those who use plaintext outbound mail by default (and know what that means).

Re: Maddy: Composable all-in-one mail server

#75

Post by andix »

Firerouge wrote: post #20

Configuration and setup wise, this looks somewhat simpler to setup than the comparable mailcow-dockerized. https://mailcow.github.io/mailcow-dockerized-docs/i_u_m_inst... I wonder how it compares in multi account management and spam, phishing, & virus blocking, is it extensible?

Mailcow is a great system. I use it and I love it.

But it's a total mess. So many different components glued together, so much that can go wrong. The configuration is scattered into hundreds of files. There is no clear split between the product and user-configuration. To change some settings, you need to make adjustments in the core product (the config files that hold everything together).

Replacing a lot of components with Maddy would probably make projects like mailcow way slimmer.

Re: Maddy: Composable all-in-one mail server

#76

Post by g_p »

aetherspawn wrote: post #16
figbert wrote: post #7

I've been using Maddy now for about a month for my email, and it's incredible. The dev says it's not caddy for email – but in my experience, it's certainly been that easy. I've got to write a longer article about this, but self-hosting email is incredibly liberating. I now own my entire digital identity. I can work on open source projects with developers around the world completely while relying only on my own capabi…

How did you get around deliverability issues?

To share one trick I found (after you've done all the DKIM/SPF/DMARC/PTR things others point out), if you still have deliverability issues to Microsoft 365 tenants, it is worth sending mail as HTML rather than plain text.

I have no idea why that helps (well, I could guess that some spam heuristic thinks plaintext email without an accompanying HTML envelope is more likely to be spam), but changing this took me from near-constant "your email went to spam" to no issues sending even things that actually look spammy (i.e. an email just containing a link that might be of interest to the recipient)

Re: Maddy: Composable all-in-one mail server

#77

Post by throw0101a »

sergiomattei wrote: post #13

This is a great initiative. The last time I remember setting up a mail server using Postfix or Dovecot was around 2015. It was a traumatizing experience. It rarely worked, all my email went to spam and I absolutely hated the amount of hackery and duct tape required to keep it working. Configuration files, missed emails... It was so unpleasant, to this day I avoid messing with mail on servers at all costs. I'd much ra…

> Lately I've been seeing an uptick of these apps making self-hosted email easier. Mail in a box, Maddy, etc. I will unconditionally support anything that makes doing this easier.

See also ISPmail (which uses Debian):

* https://workaround.org/ispmail

Re: Maddy: Composable all-in-one mail server

#78

Post by andix »

I used to run CommuniGate from Stalker on my private mail server.

It is more or less one binary and one data folder, available for all operating systems, providing a lot of functionality (SMTP, IMAP, ActiveSync, Webmail, Groupware, ...). Everything can be configured via one uniform Web UI. Multi domain, multi IP, and you could even cluster together multiple servers.

It's closed source, but offers a free license for up to 5 mailboxes.

Sadly this product died during the last 10 years and is now in an unusable state.

Re: Maddy: Composable all-in-one mail server

#79

Post by hawski »

g_p wrote: post #58
n3storm wrote: post #15

Earlier quoted context omitted.

Your mail will go to Spam too with Maddy, this is not about the MTA.

One "weird trick" I discovered with deliverability was that plaintext email from my server was rejected, but HTML email from it was accepted. For anyone with deliverability issues and mail going to spam, it might be worth trying this out (after you have sorted all the usual points like DKIM, SPF, PTR record etc.) - this obviously only helps if your IP is clean. I was surprised though, and only discovered it by accide…

What a world we live in, I always would thought the opposite. Probably it was like that before, but now maybe spammers send more plain text e-mails to appear legit. Never ending game of cat and mouse.

Re: Maddy: Composable all-in-one mail server

#80

Post by g_p »

hawski wrote: post #79
g_p wrote: post #58

Earlier quoted context omitted.

One "weird trick" I discovered with deliverability was that plaintext email from my server was rejected, but HTML email from it was accepted. For anyone with deliverability issues and mail going to spam, it might be worth trying this out (after you have sorted all the usual points like DKIM, SPF, PTR record etc.) - this obviously only helps if your IP is clean. I was surprised though, and only discovered it by accide…

What a world we live in, I always would thought the opposite. Probably it was like that before, but now maybe spammers send more plain text e-mails to appear legit. Never ending game of cat and mouse.

My guess (pure speculation) is that more spam is auto-generated via email libraries and similar, and that is producing plaintext mail to try to simplify what it's getting through the filters.

On the other hand, most human-generated mail is HTML-based, as it's written in a web-client or desktop/mobile "app client", that is using HTML to let people do bold and put pictures into their email.

I was as surprised as you when I figured this out!

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