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How to run your own mail server (2017)

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Re: How to run your own mail server (2017)

#241

Earlier quoted context omitted.

Security - I think Fastmail is pretty good at security, but I don't think there's another firm on the planet that does as well at security as Google. Specifically, I found Fastmail's implementation of 2FA to be a bit lacking. I imagine that a determined attacker would find it easier to abuse their support processes, since Fastmail's support is quite helpful whereas Google barely even responds. Spam filtering - I have…

By the way - I told our support team that you told them they were quite helpful. They are pleased to hear that feedback :) Seriously though, we have been making as much effort as possible to push the account recovery away from being an "agent decides" to following an automated process. We famously got this wrong once many years ago, and have learned from that! So the fact that our lovely support people are very helpf…

They genuinely are very helpful. I always get the feeling I'm speaking to a human being that knows enough technology to answer my questions, and has the empathy to try to understand my problem.

I remember on one occasion needing to extract billing info from a number of different accounts that were under one master account. The support explained there was no native solution, but helped me come up with a workaround. That kind of support is sadly missing from a lot of vendors.

Re: How to run your own mail server (2017)

#242

Earlier quoted context omitted.

By the way - I told our support team that you told them they were quite helpful. They are pleased to hear that feedback :) Seriously though, we have been making as much effort as possible to push the account recovery away from being an "agent decides" to following an automated process. We famously got this wrong once many years ago, and have learned from that! So the fact that our lovely support people are very helpf…

They genuinely are very helpful. I always get the feeling I'm speaking to a human being that knows enough technology to answer my questions, and has the empathy to try to understand my problem. I remember on one occasion needing to extract billing info from a number of different accounts that were under one master account. The support explained there was no native solution, but helped me come up with a workaround. Th…

I'm very proud of our support team! That's exactly the kind of help I'd expect them to give anybody :)

We are expecting people to pay money for a service which others provide "for free", so we need to differentiate ourselves, and having real humans who not only provide great service, but are located close to the technical teams and can feed quickly back to improving our service is a key differentiator for us.

Re: How to run your own mail server (2017)

#243
post #22

Then you realize the true pain of having a near-zero reputation when trying to email anything to people on Gmail, Yahoo, Live, etc, etc. Expect to go to spam even if you have DKIM, SPF, and no relaying. If anyone actually knows the secret to not having your own mail-server's mail go to spam on these bigger systems, please tell, I've Googled it for years with no success.

You have to configure a super complicated system of SEC-DNS and connect it to Postifix. Thanks to the Spaghetti Fly Monster, this guy made all of this automatically https://mailinabox.email/

Gotta love dat curl pipe sudo bash!

Re: How to run your own mail server (2017)

#244
post #22

Then you realize the true pain of having a near-zero reputation when trying to email anything to people on Gmail, Yahoo, Live, etc, etc. Expect to go to spam even if you have DKIM, SPF, and no relaying. If anyone actually knows the secret to not having your own mail-server's mail go to spam on these bigger systems, please tell, I've Googled it for years with no success.

I've been running my mail server off DO for the last ±5 years - Postfix with SPF no DKIM, DMARC - I get good delivery for Gmail and yahoo. Initially, I thought I would go full on spamassassin and clamav but thought I should hold off until I got spammed. Turns out in the last 5 years the only spammers I've got are 2 senders, one threatening to share video recorded of me on webcam to my contacts and another keeps telling me my domains' seo has expired blah blah. These are 1 or 2 times in 3 months, SpamAssassin would definitely be overkill. Apple Mail client junks them anyway. About 1 year ago I moved the setup into a docker container to better maximize the use of the $10 droplet.

Re: How to run your own mail server (2017)

#245

Earlier quoted context omitted.

I do two things: 1. Send mail via a static IP (that I pay extra for) 2. Send all mail through a reputable 'smarthost' (mine is provided by my ISP as part of the 'business' package). This fixes all sending mail problems. For extra fairy-dust, I added SPF records to my mail server IP. The BIG problem is Spam. Unless you pay for an intermediary spam filtering service, you will NEVER be on top of it. After self-hosting m…

> The BIG problem is Spam. YMMV, but a combination of graylisting, RBL and "sender address valiation" tends to drop inbound spam rate to nearly zero.

I'm currently hosting a spamassassin instance, and route incoming mail via that, however a lot still gets through :(

Re: How to run your own mail server (2017)

#246
post #22

Then you realize the true pain of having a near-zero reputation when trying to email anything to people on Gmail, Yahoo, Live, etc, etc. Expect to go to spam even if you have DKIM, SPF, and no relaying. If anyone actually knows the secret to not having your own mail-server's mail go to spam on these bigger systems, please tell, I've Googled it for years with no success.

The trick to this is not hosting your mail server with a provider which has a bad reputation.

Mine goes through a DigitalOcean droplet and my mail usually gets through (based on the assumption that if I received a reply, the other person must have received it!)

By contrast a volunteer group I'm involved with was using OVH "because it's the cheapest". Suppliers and customers were routinely telling us the emails were going to spam. Moved to another provider (no idea who, the infrastructure team does that) and the complaints fell to a trickle.

Good IP block reputation (check RBLs) + valid SPF + valid DKIM is usually enough to get mail through. Except occasionally to Hotmail... but that's Hotmail...

Re: How to run your own mail server (2017)

#247
post #30
post #22

Then you realize the true pain of having a near-zero reputation when trying to email anything to people on Gmail, Yahoo, Live, etc, etc. Expect to go to spam even if you have DKIM, SPF, and no relaying. If anyone actually knows the secret to not having your own mail-server's mail go to spam on these bigger systems, please tell, I've Googled it for years with no success.

Agreed! I've been running my own mail server for 20+ years, and I would not recommend that anybody do this on a lark. Deliverability to GMail is a huge problem for me and has been for years. I even asked friends at Google to find out what the story was. All I got back is that the mail group was so careful/paranoid it wouldn't talk to them either. I would long ago have switched over to a vendor, but I use qmail-style…

> I've been running my own mail server for 20+ years ...

Out of curiosity, where does your MTA live? Do you have a VPS? VM/instance at a cloud provider? ISP with static IP? Other?

Re: How to run your own mail server (2017)

#248
post #22

Then you realize the true pain of having a near-zero reputation when trying to email anything to people on Gmail, Yahoo, Live, etc, etc. Expect to go to spam even if you have DKIM, SPF, and no relaying. If anyone actually knows the secret to not having your own mail-server's mail go to spam on these bigger systems, please tell, I've Googled it for years with no success.

https://support.google.com/mail/answer/6227174?hl=en

I added my domain and have never had it marked as spam at any major email provider, only a few small, self-hosted servers and that was probably due to misconfiguration or high spam sensitivity. See if this might help you out.

Re: How to run your own mail server (2017)

#249

Earlier quoted context omitted.

Interesting! Maybe I should try doing the outbound via Fastmail or some other provider. I couldn't shut down my mail server entirely, but it might solve my deliverability issue.

I use postmark to do my delivery. They support outbound smtp that my internal postfix relays to and you pay per email even tho they gave me so many free credits I havent paid anything.

I was thinking about doing the same with mailgun. Do you have any obvious delivery issues with outgoing mail marked as spam?

Re: How to run your own mail server (2017)

#250

Kudos to the author for this, this is an endeavor of madness IMHO... The only thing I've ever failed to setup was a functioning mail server using Postfix and Dovecot (it was like ~2007/8). It was a circle of configuration hell I would wish on no one and since then I've never understood why anyone would want to run their own mail server. Pure, unadulterated, hell... I honestly don't even know why we have email at all…

I've been running my own mail servers since 1994. I started with smail, then sendmail, then qmail, various pop3 and imap servers, now postfix and dovecot If you set it up and do it right, which means SPF, DKIM, DMARC these days, plus obviously basics like reverse DNS, it is almost trouble free.

Making sure your service is always available isn't even necessary. Queuing and retries are built into the SMTP protocol. I run my servers off a cable modem and I easily have 99.9% availability.

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