[oskapt]

I’ve run my own mail server for decades, and if you set up SPF and DMARC correctly, you won’t have any real issues. The biggest problem I had over the years was with outlook.com blacklisting all of AWS as spam IP space, but once I contacted them and explained what I was doing, they investigated and whitelisted my elastic IP address.

[pbhjpbhj]

This comes up quite regularly, some of us have had major deliverability problems with SPF and DMARC and DKIM all set up. There are, it appears, other factors outside of one's control -- for me it was (at the time) MS apparently wouldn't receive my email (that was whitelisted, and from a 15yo domain with < one email per week outbound to Live.com) because a ip4 address of a server (not the one I was using) currently hosted by my hosting provider had previously been used for spam. There was no efficient way for me to move hosting provider and know that the same situation wouldn't be true, so I signed up for a new @live.com address and send emails to MS domains through that from my MUA (Thunderbird).

At that time MS had a third party that managed this, you could pay them to do something that would basically get you whitelisted; but this was for an SME and the cost was prohibitive for the potential benefit.

If you moved server on AWS presumably you'd have to go the same route again - who did you contact? - would you be 100% confident you'd get whitelisted?

[RcouF1uZ4gsC]

> I’ve run my own mail server for decades, and if you set up SPF and DMARC correctly, you won’t have any real issues.

I wonder if the fact that you have done it for decades helps with you avoiding spam filters. This may not be the experience for someone who newly sets up their own email server.

[indymike]

> This may not be the experience for someone who newly sets up their own email server.

I've set up mail servers many times over many decades and it's not as hard as a lot of people think. For a reasonably secured and maintained personal server, you'll have to learn about SPF, DMARC, and do more detailed DNS setup than you do to get a quick website up, but once up, everything should go well... so long as you and your family behave.

For businesses, especially those with enthusiastic marketing teams, it's harder because all it takes is a a bug in some transactional email code, or a bad email from a well meaning sales rep to some email list from a "digital marketing" forum to completely wreck your server's reputation.

[na85]

>For businesses, especially those with enthusiastic marketing teams, it's harder because all it takes is a a bug in some transactional email code, or a bad email from a well meaning sales rep to some email list from a "digital marketing" forum to completely wreck your server's reputation.

Working as intended if you ask me.

[vbezhenar]

I think that IP address reputation is the biggest factor in mail deliverability for small servers. So when you've bought new VPS, it will be hit or miss, whether your IPv4 address was used maliciously before or not.

[cube00]

If you get caught by this you can request "delivery mitigation" (i.e. removal from their IP blacklist) here:

http://go.microsoft.com/fwlink/?LinkID=614866

You can also join the "Smart Network Data Service" (SNDS) program, which can alert you in the future if you are re-listed and sometimes will provide additional information about why the IP has been listed.

https://postmaster.live.com/snds/addnetwork.aspx

[baobabKoodaa]

> If you get caught by this you can request "delivery mitigation" (i.e. removal from their IP blacklist) here: http://go.microsoft.com/fwlink/?LinkID=614866

Microsoft only provides delivery mitigation for large-volume senders. Small-volume senders (i.e. not spam senders) will not be provided delivery mitigation. That's from my personal experience anyway.

> You can also join the "Smart Network Data Service" (SNDS) program, which can alert you in the future if you are re-listed and sometimes will provide additional information about why the IP has been listed.

Unless you are a large-volume sender, you will not be able to get ANY information out of SNDS.

[codetrotter]

What software do you use for your mail server and client? I’m looking to replace my current self-hosted setup with something else.

Currently I am running Postfix on my FreeBSD server, and not using SpamAssasin. I've had this setup for years and it's less than ideal but it's at the point where it's been hard to justify the time I'd have to spend setting up a better configuration.

I ssh into the server and read mail using mutt. I also have notmuch installed but only use it a little bit now and then and still relying primarily on mutt. I'm not really happy about mutt either. It's neat in its own way but it's also a bit of a drag to use and even though I enjoy using the command line I don't feel like mutt is really a good fit for how I would like to use mail.

Ideally I think I'd want something similar to how some of the features of GMail work, but mainly in terms of tagging and filtering. As for a web based interface, I don't want that part really. But still very much interested in knowing of web interfaces too from people that use them and like them.

But most of all, what I am looking for is a server that has good and easy to use filtering, that is open source and runs on FreeBSD or Linux, and native clients for macOS and iOS that integrate well with the server including the tagging and filtering stuff.

[na85]

I have a dovecot+postfix+rspamd setup and I read my mail with apple mail.app, thunderbird, and FairEmail on my phone. That latter app is excellent and I highly recommend.

[eikenberry]

Depends who you are trying to send email to. There are email providers that use IP blacklist maintainers that require you to pay a fee to keep off their blacklist if you are not a big provider (eg. they blacklist all VPS hosting companies). This was the final straw that had me switch to using a provider for SMTP (not MX, I run it still).

[ancarda]

How did you know to contact Microsoft to have them whitelist your IP? Was that from a DMARC report?

This is the sort of thing that puts me off self-hosting email, as much as I'd like to do it -- it seems like a huge amount of effort, tracking down who I need to shout at this week to have them whitelist my IP address.

[heipei]

Microsoft doesn’t send DMARC reports which made discovering delivery issues all the more problematic.