7 ms·

Long time self-hosted email user, then long time Gmail user. Playing with your own server is fun, and I really enjoyed it. But things do go wrong, and they go w

Long time self-hosted email user, then long time Gmail user. Playing with your own server is fun, and I really enjoyed it. But things do go wrong, and they go wrong at the least convenient times. I've lost a whole day of a holiday trying to find a place with internet so I could log in and fix some small thing that had broken (I also hosted for a handful of other people, not all of whom were on holiday). And I've had that sinking feeling when you realise that that important email you've been waiting for has been sitting for a day and a half behind a crashed/misconfigured service somewhere. Good luck with your endeavour, it is if nothing else a learning experience. But it's important to keep in mind that if email is a critical tool for you (it is for many people, ymmv), toying with it may not be the best idea.

hueving 9y ago
How did the service suddenly become misconfigured?
- mseebach 9y ago
  I don't remember the details, but it probably didn't become misconfigured, it would always have been misconfigured, just one particular combination of factors that hadn't been seen before suddenly got caught. I remember at one point that an org I did email for couldn't receive email from a particular other organisation. Turned out that I had configured our MTA to accept TLS, and theirs presented an invalid cert, so the connection was rejected. This wasn't the situation I referred to, because this caused email to bounce hard, so people just routed around (yay for having people have professional contacts send to their hotmail instead). Or whatever. I remember the feeling, not the mistake that caused it.
ozim 9y ago
You know that some corporations consider GMail as spamhole and block mails sent from it. There is no perfect solution.
- mseebach 9y ago
  Yeah, that seems rather unlikely. Do you have some references for that claim?
- michaelmrose 9y ago
  Gmail has 1 billion users. Blocking a massive chunk of all possible users seems sort of insane are you sure you didn't mistype yahoo?
  - mseebach 9y ago
    I vaguely suspect that GP may refer to the fact that certain corporations block access to the Gmail web interface (and the other big providers) from their network, typically for auditing purposes, in a way to a personally run mail server might evade. In those cases, actually accessing your personal mail server would typically be a gross breach of conduct and lead to immediate termination for cause if caught. This, of course, has nothing at all to do with the deliverability of email from those services, even to these same organisations (they can audit what goes through their own servers, so that's fine). But, that's a guess, and I obviously can speak on GPs behalf.
    - ozim 9y ago
      Yes and also they block receiving emails from GMail domain for security purposes. So if you want to email someone internal in big co, you have to do it from your own domain. I suppose it is not only for GMail. Probably Yahoo, Microsoft also but I only had one guy trying to use GMail sending mail to corporate users.
      - mseebach 9y ago
        Before you said "spamhole", now it's security. In both cases it makes literally no sense to block Gmail and allow random personal domains. I suppose the setup could be based on whitelisting domains, and because Gmail is so big, they won't whitelist it, and it also won't receive emails from anything random, but from specific personal domains. But such a setup specifically isn't for communicating with the world at large, and not any kind of widespread practice. Also, you should be using your own domain with Gmail (or any other provider) so you aren't tied to anyone, anyway.
jbergstroem 9y ago
I'm just now experiencing the direct opposite with Fastmail. Used it to avoid setting up my own mail server for a ~50 user gitlab instance. Went from trial user to paying for a full year and one day later my account is now blocked. Found this message in the first rejected email: "We couldn't figure out what the email is for. Please create your issue or comment through the web interface.". Can't send mail through webmail interface. Can't access IMAP nor SMTP. Support emails from their own support doesn't go through. So, without any means to control it myself I'm now in the mercy of fastmail support unless I set up my own postfix/dovecot in the meantime. I guess it goes both ways.
- dasyatidprime 9y ago
  … hang on, what plan did you ask for for this, and what kind of mail were you actually sending/receiving? As far as I'm aware, Fastmail charges per-user, and isn't advertised as suitable for sending automated mail through. It sounds very strange to use it as a replacement for “setting up a mail server for a GitLab instance”.
  - jbergstroem 9y ago
    What ToS am I violating exactly? I’m _well_ within limits for both incoming and outgoing and all recipients sign up for receiving the emails. The gitlab wiki even uses fastmail as an example for smtp.
    - jbergstroem 9y ago
      For record-keeping: got a reply two days later from support saying that they do not support sending notification emails, which this is classified as.
cortesoft 9y ago
I try to find a balance - I run my own mail server on a digital ocean droplet, but I use gmail to fetch email from it, and I use gmail as my sender. I get the best of both worlds; I don't have to worry about being blocked when I send things, and if I ever have issue with gmail, I can stop using them without losing my email address.

hueving 9y ago

How did the service suddenly become misconfigured?

mseebach 9y ago
I don't remember the details, but it probably didn't become misconfigured, it would always have been misconfigured, just one particular combination of factors that hadn't been seen before suddenly got caught. I remember at one point that an org I did email for couldn't receive email from a particular other organisation. Turned out that I had configured our MTA to accept TLS, and theirs presented an invalid cert, so the connection was rejected. This wasn't the situation I referred to, because this caused email to bounce hard, so people just routed around (yay for having people have professional contacts send to their hotmail instead). Or whatever. I remember the feeling, not the mistake that caused it.

ozim 9y ago

You know that some corporations consider GMail as spamhole and block mails sent from it. There is no perfect solution.

mseebach 9y ago
Yeah, that seems rather unlikely. Do you have some references for that claim?
michaelmrose 9y ago
Gmail has 1 billion users. Blocking a massive chunk of all possible users seems sort of insane are you sure you didn't mistype yahoo?
- mseebach 9y ago
  I vaguely suspect that GP may refer to the fact that certain corporations block access to the Gmail web interface (and the other big providers) from their network, typically for auditing purposes, in a way to a personally run mail server might evade. In those cases, actually accessing your personal mail server would typically be a gross breach of conduct and lead to immediate termination for cause if caught. This, of course, has nothing at all to do with the deliverability of email from those services, even to these same organisations (they can audit what goes through their own servers, so that's fine). But, that's a guess, and I obviously can speak on GPs behalf.
  - ozim 9y ago
    Yes and also they block receiving emails from GMail domain for security purposes. So if you want to email someone internal in big co, you have to do it from your own domain. I suppose it is not only for GMail. Probably Yahoo, Microsoft also but I only had one guy trying to use GMail sending mail to corporate users.
    - mseebach 9y ago
      Before you said "spamhole", now it's security. In both cases it makes literally no sense to block Gmail and allow random personal domains. I suppose the setup could be based on whitelisting domains, and because Gmail is so big, they won't whitelist it, and it also won't receive emails from anything random, but from specific personal domains. But such a setup specifically isn't for communicating with the world at large, and not any kind of widespread practice. Also, you should be using your own domain with Gmail (or any other provider) so you aren't tied to anyone, anyway.

jbergstroem 9y ago

I'm just now experiencing the direct opposite with Fastmail. Used it to avoid setting up my own mail server for a ~50 user gitlab instance. Went from trial user to paying for a full year and one day later my account is now blocked. Found this message in the first rejected email: "We couldn't figure out what the email is for. Please create your issue or comment through the web interface.". Can't send mail through webmail interface. Can't access IMAP nor SMTP. Support emails from their own support doesn't go through. So, without any means to control it myself I'm now in the mercy of fastmail support unless I set up my own postfix/dovecot in the meantime. I guess it goes both ways.

dasyatidprime 9y ago
… hang on, what plan did you ask for for this, and what kind of mail were you actually sending/receiving? As far as I'm aware, Fastmail charges per-user, and isn't advertised as suitable for sending automated mail through. It sounds very strange to use it as a replacement for “setting up a mail server for a GitLab instance”.
- jbergstroem 9y ago
  What ToS am I violating exactly? I’m _well_ within limits for both incoming and outgoing and all recipients sign up for receiving the emails. The gitlab wiki even uses fastmail as an example for smtp.
  - jbergstroem 9y ago
    For record-keeping: got a reply two days later from support saying that they do not support sending notification emails, which this is classified as.

cortesoft 9y ago

I try to find a balance - I run my own mail server on a digital ocean droplet, but I use gmail to fetch email from it, and I use gmail as my sender. I get the best of both worlds; I don't have to worry about being blocked when I send things, and if I ever have issue with gmail, I can stop using them without losing my email address.