Aren't you afraid of missing emails?

No I simply don't care. People who want to reach me, will reach me.
Most professional servers will do so automatically and will retry for days.
For my private Cloudron the mail throughput is not huge. Also, my restarts are outside the normal business hours in Germany.
And most people and even companies in Germany don't really send mails in the middle of the night.
And if they do so, back to the first sentence

@SansGuidon said in /r/selfhosted are not big Cloudron fans:

How much effort are you dedicating to maintain your server reputation to avoid your emails to end up in spam, or on the other hand, how much effort you dedicate in tuning spam assassin rules etc?

Private Server 0 % effort.
My IPv4 and IPv6 has "such a good reputation"* after ~5 years that I can not recall the last failed mail.

• What is my reputation? No Idea
  Oh I once added my mail server to https://postmaster.google.com/ maybe that also helped even if I don't see any data because I do not qualify since I do not send 100+ mails a day
  There is also https://sendersupport.olc.protection.outlook.com/snds/ but never used it.

tuning spam assassin rules

In @d19dotca I trust and his might has not yet failed me.
Thanks again @d19dotca
https://forum.cloudron.io/post/105256

How do you handle those cases? Aren't you afraid of missing emails?

I think mail servers just automatically keep trying and so such things as short amounts of down time don't make any real practical difference, so speaking personally I'm not at all afraid of missing emails (and I'd add that when I was on Google I did miss quite a few emails that were regularly falsely marked as spam by Google).

@SansGuidon said in /r/selfhosted are not big Cloudron fans:

How much effort are you dedicating to maintain your server reputation to avoid your emails to end up in spam

Personally I don't do anything other than checking the IP of a new server isn't on blocklists before setting things up on it. I know others here e.g. @marcusquinn have used various services email warm up services (as e.g. described here https://www.lemlist.com/blog/warm-up-email-account ) but I've not found the need (the only bulk emails I send go via Ghost which requires Mailgun who already have fairly decent delivery rates)

or on the other hand, how much effort you dedicate in tuning spam assassin rules etc?

I've not bothered myself, but @d19dotca has spent quite a lot of time fine tuning these and regularly shares his rules - and many others here are successfully using them

As mentioned previously, the primary issue I've personally his is M$ blocking my emails (because my IP has ended up in a big wide range of IPs where there is one bad egg and they've blocked the whole range. Generally getting your server provider to contact M$ about this sorts it out pretty quickly)

there is a bigger risk IMHO that it would go downtime e.g Cloudron updates/restarts

Email is resilient. If a sending mailserver cannot deliver a mail to your server, it will continue trying to do so. I think most commonly the sending server will try for two days before generating a non delivery message to the original sender.

For sending out its best to use a mail relay provider. This costs extra, but then you have someone else who is managing the reputation of your outgoing relay.

@SansGuidon Dependent on the source mail server system if it is possible to migrate such things.
Certain providers do not offer this information on a programmatic endpoint.
Thus, my answer, it depends.
If possible to be coded and automated, yes.

If 100+ Users calendars, rules need to be migrated by hand
That takes time and money and might be better to be done be the users themselves then.

In the case of the 300+ User set up the source mail server did offer everything via. IMAP or other means, thus I could code the whole migration.

Hey @BrutalBirdie I'm interested in your experience with email availability, as if I host my email server, there is a bigger risk IMHO that it would go downtime e.g Cloudron updates/restarts, etc. How do you handle those cases? Aren't you afraid of missing emails? How much effort are you dedicating to maintain your server reputation to avoid your emails to end up in spam, or on the other hand, how much effort you dedicate in tuning spam assassin rules etc?

EDIT: it seems that this app could be a good alternative to FastMail for my taste and needs but the packaging seems stuck. https://forum.cloudron.io/topic/1070/cypht-lightweight-open-source-webmail-application-written-in-php-and-javascript/42
I'm curious to try it.

Login is username demo and password demo

I think you mean cloudron and cloudron

If 100+ Users calendars, rules need to be migrated by hand
That takes time and money and might be better to be done be the users themselves then.

In the case of the 300+ User set up the source mail server did offer everything via. IMAP or other means, thus I could code the whole migration.

If you maybe need a partner for such migrations, happy to help.
I've migrated 300+ User mail setups to Cloudron with inboxes and everything.

Only recent issue was the missing IP6 PTR record that I didn't see a notification for needing to add.

Otherwise, been reliable all these years, and much happier to have my email (well my end at least) safe from AI being trained on it.

Keeping it secure, private, and user-friendly long-term — that’s the real challenge for me.

Cloudron does it all for you. Well, at least well enough for many of us here.

But if you want to outsource it someone else, fair enough.

To be honest it took me a while to make the leap too, but I'm glad I eventually did, even though I've had the odd deliverability to M$ issue due to their shitty systems.

If I choose to self-host it, I want full control without spending hours checking logs to make sure I'm not being hacked or silently blacklisted. I don’t want to build half a dozen tools just to compensate for the lack of UX or decent API. I also don’t want to waste time writing migration scripts and gluing things together.

Spinning up an email server and connecting a webmail client is one thing. Keeping it secure, private, and user-friendly long-term — that’s the real challenge for me.

Don't be afraid of self-hosting email. We need to take steps to get freedom back.

To that notion, IRC did not used to be fashionable in Corp land until someone reinvented it with Slack.

Don't be afraid of creating something new that eclipses IRC, Email and all else, like Signal.org and ConfidantMail.org did. Now with the benefit of code assisting LLMs.

It's May of 2025, Microsoft is shutting down Skype and we don't have a default way of sending files (or making calls) to each other from our devices that is effortless. We have to rely on 3rd party Apps that get so complex your Mom can't use it and it's easier to just think of FTP or Email.

It's time to bring back delight to computing and the internet, not control and restrictions.

Isn't that why we're on Cloudron.io ?

As far as I know, with a SaaS mail server you can't see delivery or bounce messages from sources.

You have no idea if a sender mail server is on a whitelist, even though the server is on a spam list - only because of “backroom conversations” between an inner circle.

I was told by a customer that he had no chance to deliver mails to a large service provider because his sender IP was on a spam filter list. It took almost 10 days to get the IP off the list.

2 weeks later, the customer told us: we are not receiving any mails from the service provider. Because we use the same spam filter lists, the mails were rejected because the service provider's mail server was on the spam filter list.

Because the service provider didn't care, we had to lower our shield to receive emails from them.

It's unfair just because of the flies and shit.
Some are equal some are more equal.

I borrow a saying from sport and apply it to open source:
“Created by the poor, stolen by the rich.” -> “Created by open source, stolen by closed source”

Don't be afraid of self-hosting email. We need to take steps to get freedom back.

Y! has severely gone downhill, and many Virgo types want to organize where every email belongs and aren't fond of labels from G!

What's one to do once those options are no longer options?

the web mails I see listed seem outdated in term of UX and look more like toys than like serious alternatives to webmails clients I'm used to.

Yeah, this is the biggest issue IMHO. None of the open source webmail clients are really up to scratch. But they are all usable. I mostly use SnappyMail but it does have some glitches and every now and then I go over to Roundcube for some reason or another. Nextcloud Mail isn't bad either. And we also have SoGo mail. It's easy to use any of them. Or just use a Desktop app like Thunderbird.

and a dead internal link:
https://docs.cloudron.io/guides/community/smtp-relay-configuration.md