[badgersandjam]

Don't bother running a mail server. It's hell. I did from 1998 until about last week. I started running it on a cable modem with an old Compaq desktop, migrated to a dedicated server (which hosted a load of other stuff) and finally onto VMs.

I have spent hours getting myself of blacklists after entire IP ranges were reported. I've spent hours working out why the hell Postfix won't talk to dovecot on a local socket, upgrading Linux distributions, postfix and dovecot and being fucked over by config format changes and periodically losing entire mailboxes to IMAP bugs. Oh and SELinux - hours of it.

The thing that finally killed it for me was Yahoo. My landlord uses Yahoo mail for comms and Yahoo just decided to stop accepting delivery from my server. It took a phone call from me asking him why he hadn't sorted something for me and for him to tell me that he didn't get the email to discover this. So I dredged through the logs, found an error from yahoo's mail servers saying I need to hit a web form to prove I was a legitimate sender. So I did that, and nothing, not a sausage happened. Googling around says I need to wait 6 months before submitting the request again.

I have no power in this situation. I can't email my landlord. I need to do business, not piss around with politics.

So in a fit of anger, I blasted my VM on Linode, went to my local supermarket, bought a Moto G2 in cash to replace my Lumia 630 (which was doing IMAP) that I just smashed the screen on, signed up for Google Apps free trial and just moved the domain over to that.

Just can't be fucked with it any more. I run "inbox zero" (i.e. I delete religiously) so there is no cost for me to migrate.

I don't care if they read my email or shop me to the feds; I'm tired of herding servers and software these days. A decade ago I could quite happily spend all day doing it but I have better things to do now.

[darklajid]

Funny enough my own server ONLY had problems with .. GMail so far.

From two days ago: "Let's try this GPG setup, write a mail to my coworker's private GMail account and get a verification that everything checks out on his side".

GMail refuses the PGP/MIME mail, bounces after end of DATA, as 'Spam'. What?

Send the same mail to my GMail account. Works.

Send the same mail to my brother's GMail account. Works.

Send to coworker again: Bounces after DATA, refers to a useless website that offers Google's policies for bulk mails again.

Send a plain text mail to coworker, complaining about Google's mess: Accepted.

So.. Takeaway:

- Google randomly rejects mails from my server, without anything I can do and without providing any information WHY it would do that. Not filing as spam, rejecting outright.

- Google only did that with a mail that is unreadable (PGP/MIME). Coincidence? Make of that what you will..

I will keep my server though. And loudly complain to people that run broken setups. In this case I complained to this coworker of mine and wrote lots of expletives directed at Google - and the issue is resolved for me now. People with GMail addresses that don't get my mail are frankly not my problem and for friends and family I might be able to exert enough pressure to fix the problem.

[shocks]

I moved to runbox a few months ago and I'm pretty happy. I'll echo your "don't even bother running your own mail server". Been there. Done that. No thanks. Horrible.

[xorcist]

YMMV. I've also ran my own since 1998. It's worked almost flawlessly from the start. A stock Debian system that I've kept up to date just keeps on ticking.

The only trouble I've had has been sporadically with Hotmail. Still don't know why, I get the bounce and contact the recipient from somewhere else. Even Gmail has these problems from time to time.

I just wanted to stick in another datapoint in the discussion, so not every post is about how awful email is. Sometimes it just works.

[beachstartup]

right - for individuals who are trying to run a server on a shared server/network (VM), you're going to have a bad time... a real bad time.

however, it's not this bad if you have a 'real' infrastructure i.e. a colocated environment with your own IP space. it sounds like you were mainly dealing with the fallout from bad behavior from your neighbors on the shared network.

having said all that, it still might be worth a switch if you use google apps a lot (we do) because of the integration with gmail. we switched and now use IMAP to access our company google apps gmail. i really dislike the web interface.

[badgersandjam]

Actually I had a nice dedicated box until 2013 at a reputable host in the UK. Unfortunately I no longer wished to fish out for £95/month for it. Still had problems even though the thing was well maintained and there were no bad neighbours. It was less noisy than a VM at Linode however, so you're right there.

[beachstartup]

yeah, i meant if you actually have ARIN IP space or get allocated at least a routed /24 from a tier 1 ISP... not a cheap dedicated box in some datacenter that suffers from the same problems as shared VM networks.

[icebraining]

I have a compromise: run my own server but pass outbound messages through mandrill. Most of my mail is inbound anyway.

It took a few hours to configure exim + dovecot + sieve plugin, but it has been running unattended for over a year (upgrades are automatically installed using unattended-upgrades[1]).

Spam is not a problem, I just use a different address for each service, and ban it if it starts getting spam. As an additional benefit, I know who failed to keep it private.

[1] https://wiki.debian.org/UnattendedUpgrades

[derekp7]

There is a hybrid approach -- run a local mail server for receiving mail, and configure your Gmail account set the "From:" address to your domain, and forward any mail to Gmail to your domain. This way you are still mostly in control of your mail, but with the sending reliability of a major service.

[glomph]

This basically negates half the privacy though. And given most of the mail you recitative will be sent from gmails servers anyway...

[derekp7]

For myself, I'm not too worried about privacy (if I want that I'll use PGP). I'm more concerned about vendor lock in. Because as long as people are sending you mail to a domain you own, you can change the sending email provider to any other one that allows a custom From: address. Now from a practical side, I currently let Google Apps completely handle my domain's email, but I can yank it off there at a moments notice if I had to (i.e., if Google decided that I'm not allowed to host my domain there anymore).

[badgersandjam]

Interesting approach and one I hadn't considered. Thanks for the heads up.