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I used to run mail server for a large corporation in the late 90s. I always get really excited and nostalgic about running my own mail server when I see these a

by baz00 3y ago

I used to run mail server for a large corporation in the late 90s. I always get really excited and nostalgic about running my own mail server when I see these articles. I have a spare domain I use for testing stuff on so occasionally I'll futz with postfix and dovecot for a bit etc and get something working on Vultr or some other cheap VPS. Then I'll spend an hour getting Thunderbird and K-9 working and I'll send and receive a few emails. Then I'll remember I just spent 6 hours of my Saturday fucking around with it and now have to live with it and maintain it. So I go crawling back to outlook.com like the pathetic corporate whore I am and go and do something less painful the day after. I'll just keep my private comms off email.

chatmasta 3y ago
I'd like to be a purist about email, but I just can't bring myself to care, because as long as my correspondent is a corporate whore, why shouldn't I be too? A copy of the email is going to end up on their servers anyway. In other words, I can only protect email from my provider as long as everyone else on the email protects it from theirs. And it only takes one gmail user on the thread to ruin it for everybody. If I'm corresponding with people who also care about this kind of thing, we aren't using email. If we absolutely have to, then we can encrypt it with PGP. My email use cases are: (1) b2b professional emails, which you expect to be retained for compliance, etc. and (2) transactional emails, which my provider unavoidably has access to and which I protect with strong passwords and 2FA. (That said, I would like to obscure the list of my internet accounts from google, so maybe one day I'll migrate my transactional emails somewhere else.)
- ishandotpage 3y ago
  The corporates are pretty good at keeping self hosters emails out of their user's inboxes citing "Spam"
  - radiowave 3y ago
    One pragmatic solution to this is to use an email relay service to handle the outbound mail. Now, the hair-shirt self hoster's response to this idea might be, "But that means trusting a third party!" And indeed it does. But as the parent comment points out, in the vast general case we're committed to trusting whichever third parties our correspondent uses (or finding alternive means of communication.)
  - Gigachad 3y ago
    You can self host and reach inboxes. You just have to have all of the optional headers/dns stuff set up, and have a domain and IP address in good reputation. Probably also having the whole block in good reputation. Realistically an absolute fuckload of spam and not a lot of genuine email comes out of residential and cheap VPS hosts IPs so they already have a negative rep.
    - dorfsmay 3y ago
      That sort of work but not all the time, your messages still end up in spam a lot when trying to reach somebody you haven't exchanged email with before.
    - dspillett 3y ago
      I do self host. You have to have all DNS markers set right and DKIM working right, but that isn't complicated really. The good reputation IP range is the biggest problem. I have a more expensive ISP at home that takes its network seriously, so I look more like a commercial interest in that regard. There are decent services that will act as relay for you and probably cost less than such an ISP (or a similarly more expensive VPS provider that takes priority care of related things) if outgoing SMTP is your main reason for considering one.
  - Ayesh 3y ago
    This certainly seems to be the consensus about self hosting email, but but I'm now convinced otherwise. I send a couple newsletters (one tech related, other for marketing for a coffee shop/bakery I own), and it was fairly easy to land on inboxes. Now, I don't know with a 100% certainty that they were delivered, but if DMARC records and bounces are anything to go by, self hosted emails aren't all that hard. When you buy a VPS, it helps to check if the IP you receive is already blacklisted. After that, it's easy to use some outside service to monitor DMARC responses and blacklist. There are about 40 black list databases. My domains and the IP address are on none of them.
  - humanxperiments 3y ago
    [flagged]
  - smartbit 3y ago
    That might change now Europeans have a stick called DSA & DMA https://en.wikipedia.org/wiki/Digital_Services_Act https://en.wikipedia.org/wiki/Digital_Services_Act
- sodality2 3y ago
  For me, it’s control over the domain. I can change providers at a whim. In my preteens I stupidly set up a handful of alternate google accounts for various things. They all link back to my personal main account which I have used for much of my life. If Google’s abstract machine learning algorithm ever deems my crimes punishable by extreme pain (seriously, imagine being locked out of paypal, banking, credit cards, loans, contact with businesses, etc. for me it would be my main business point of contact as well), this would be disastrous. I don’t mind about the privacy (I consider email broken anyway), I care about control.
  - doubled112 3y ago
    Control over the domain is 100% my biggest anxiety with mail. I use Outlook with a family account, and they used to allow custom domain aliases. All of my email is addressed to addresses on my domain. It's actually a pretty good value for 4 people. If they ever decide suddenly I'm out or they're out, I'll spin up a mail server somewhere else while I figure out my next move
    - TheNewsIsHere 3y ago
      Effective today (November 30), the ability to create new addresses has been disabled. They’ve been working hard to remove features from that capability. I assume it was either more than they could justify based on adoption rates, a nightmare to maintain, or seeing more abuse than they want to manage. My anxieties over email match yours. I used to run my own email server but the entire IP range I was in got blacklisted by Proofpoint, and they were thoroughly uninterested in helping unless I owned the entire IP range and could prove it. The ISP didn’t seem to care, and at the very same time Microsoft added the same range to their lists, which meant I wasn’t able to correspond with an attorney. That was in June and by August I’d moved completely to Fastmail. I haven’t looked back, though I do sometimes miss managing my own email server.
      - doubled112 3y ago
        Ahh yes, I remember them announcing this. I'm not planning on adding new people to my immediate family so I'm OK for now. I've used Fastmail in the past and it was a very good experience. Pricing for four people tipped me towards the MS Family plan.
- defanor 3y ago
  > I'd like to be a purist about email, but I just can't bring myself to care, because as long as my correspondent is a corporate whore, why shouldn't I be too? A copy of the email is going to end up on their servers anyway. No immediate confidentiality is achievable by using a trusted mail server while interacting with untrusted ones, but doing what seems right often works as an improvement. I find it analogous to, among other things, not throwing garbage on the ground: by carrying it to a trash bin, you don't make all streets clean at once, and it may be an inconvenience, but once more people do it, streets do become cleaner. And even if others keep just dumping trash on the ground, it may be nice to know that you don't contribute to the unpleasantness. Likewise with a multitude of other areas, including good practices in programming and administration, good manners: it is unfortunate that not everyone follows them, offsetting the effort put by those who do, but it is not necessarily a reason to give up.
jesterson 3y ago
I read those comments about maintenance and "fucking around" in HN quite often and it keeps me wondering what are those people "fucking around" with. Running my own mail server for 25+ years. 50+ domains, quite a number of messages daily. Most recent maintenance was few years ago caused by Apple phasing out procedure for push certificate generation (I use apple push for mail delivery). e-mail has a learning curve for sure, but once everything is set up properly, there is no maintenance whatsoever, if you know what you are doing.
- baz00 3y ago
  Well last time I had to fuck around was because the entire IP ranged ended up on an RBL and I couldn't deliver to half the people I needed to. Oh and then there was that time that Yahoo did its thing and asks you to fill in a web form to continue delivering to them, the URL of which is neatly hidden in an SMTP response message. If you get that form wrong or they don't like the answers they will just ignore you for 6 months.
INTPenis 3y ago
>I'll just keep my private comms off email. It's not just about keeping your private communication private, it's about relying on your e-mail address being there. As long as you use someone elses domain you're vulnerable. The big providers can shut it down whenever they want. One solution is to use a custom domain that guarantees some sort of ownership. For example certain ccTLDs have more protection for private owners of their domains. And then use providers who support custom domains.
- baz00 3y ago
  I've got a domain which I forward my primary address to my outlook box. I just reply from outlook.com. I've had the account since 1999.

by baz00 3y ago

chatmasta 3y ago

I'd like to be a purist about email, but I just can't bring myself to care, because as long as my correspondent is a corporate whore, why shouldn't I be too? A copy of the email is going to end up on their servers anyway. In other words, I can only protect email from my provider as long as everyone else on the email protects it from theirs. And it only takes one gmail user on the thread to ruin it for everybody. If I'm corresponding with people who also care about this kind of thing, we aren't using email. If we absolutely have to, then we can encrypt it with PGP. My email use cases are: (1) b2b professional emails, which you expect to be retained for compliance, etc. and (2) transactional emails, which my provider unavoidably has access to and which I protect with strong passwords and 2FA. (That said, I would like to obscure the list of my internet accounts from google, so maybe one day I'll migrate my transactional emails somewhere else.)

ishandotpage 3y ago
The corporates are pretty good at keeping self hosters emails out of their user's inboxes citing "Spam"
- radiowave 3y ago
  One pragmatic solution to this is to use an email relay service to handle the outbound mail. Now, the hair-shirt self hoster's response to this idea might be, "But that means trusting a third party!" And indeed it does. But as the parent comment points out, in the vast general case we're committed to trusting whichever third parties our correspondent uses (or finding alternive means of communication.)
- Gigachad 3y ago
  You can self host and reach inboxes. You just have to have all of the optional headers/dns stuff set up, and have a domain and IP address in good reputation. Probably also having the whole block in good reputation. Realistically an absolute fuckload of spam and not a lot of genuine email comes out of residential and cheap VPS hosts IPs so they already have a negative rep.
  - dorfsmay 3y ago
    That sort of work but not all the time, your messages still end up in spam a lot when trying to reach somebody you haven't exchanged email with before.
  - dspillett 3y ago
    I do self host. You have to have all DNS markers set right and DKIM working right, but that isn't complicated really. The good reputation IP range is the biggest problem. I have a more expensive ISP at home that takes its network seriously, so I look more like a commercial interest in that regard. There are decent services that will act as relay for you and probably cost less than such an ISP (or a similarly more expensive VPS provider that takes priority care of related things) if outgoing SMTP is your main reason for considering one.
- Ayesh 3y ago
  This certainly seems to be the consensus about self hosting email, but but I'm now convinced otherwise. I send a couple newsletters (one tech related, other for marketing for a coffee shop/bakery I own), and it was fairly easy to land on inboxes. Now, I don't know with a 100% certainty that they were delivered, but if DMARC records and bounces are anything to go by, self hosted emails aren't all that hard. When you buy a VPS, it helps to check if the IP you receive is already blacklisted. After that, it's easy to use some outside service to monitor DMARC responses and blacklist. There are about 40 black list databases. My domains and the IP address are on none of them.
- humanxperiments 3y ago
  [flagged]
- smartbit 3y ago
  That might change now Europeans have a stick called DSA & DMA https://en.wikipedia.org/wiki/Digital_Services_Act https://en.wikipedia.org/wiki/Digital_Services_Act
sodality2 3y ago
For me, it’s control over the domain. I can change providers at a whim. In my preteens I stupidly set up a handful of alternate google accounts for various things. They all link back to my personal main account which I have used for much of my life. If Google’s abstract machine learning algorithm ever deems my crimes punishable by extreme pain (seriously, imagine being locked out of paypal, banking, credit cards, loans, contact with businesses, etc. for me it would be my main business point of contact as well), this would be disastrous. I don’t mind about the privacy (I consider email broken anyway), I care about control.
- doubled112 3y ago
  Control over the domain is 100% my biggest anxiety with mail. I use Outlook with a family account, and they used to allow custom domain aliases. All of my email is addressed to addresses on my domain. It's actually a pretty good value for 4 people. If they ever decide suddenly I'm out or they're out, I'll spin up a mail server somewhere else while I figure out my next move
  - TheNewsIsHere 3y ago
    Effective today (November 30), the ability to create new addresses has been disabled. They’ve been working hard to remove features from that capability. I assume it was either more than they could justify based on adoption rates, a nightmare to maintain, or seeing more abuse than they want to manage. My anxieties over email match yours. I used to run my own email server but the entire IP range I was in got blacklisted by Proofpoint, and they were thoroughly uninterested in helping unless I owned the entire IP range and could prove it. The ISP didn’t seem to care, and at the very same time Microsoft added the same range to their lists, which meant I wasn’t able to correspond with an attorney. That was in June and by August I’d moved completely to Fastmail. I haven’t looked back, though I do sometimes miss managing my own email server.
    - doubled112 3y ago
      Ahh yes, I remember them announcing this. I'm not planning on adding new people to my immediate family so I'm OK for now. I've used Fastmail in the past and it was a very good experience. Pricing for four people tipped me towards the MS Family plan.
defanor 3y ago
> I'd like to be a purist about email, but I just can't bring myself to care, because as long as my correspondent is a corporate whore, why shouldn't I be too? A copy of the email is going to end up on their servers anyway. No immediate confidentiality is achievable by using a trusted mail server while interacting with untrusted ones, but doing what seems right often works as an improvement. I find it analogous to, among other things, not throwing garbage on the ground: by carrying it to a trash bin, you don't make all streets clean at once, and it may be an inconvenience, but once more people do it, streets do become cleaner. And even if others keep just dumping trash on the ground, it may be nice to know that you don't contribute to the unpleasantness. Likewise with a multitude of other areas, including good practices in programming and administration, good manners: it is unfortunate that not everyone follows them, offsetting the effort put by those who do, but it is not necessarily a reason to give up.

jesterson 3y ago

I read those comments about maintenance and "fucking around" in HN quite often and it keeps me wondering what are those people "fucking around" with. Running my own mail server for 25+ years. 50+ domains, quite a number of messages daily. Most recent maintenance was few years ago caused by Apple phasing out procedure for push certificate generation (I use apple push for mail delivery). e-mail has a learning curve for sure, but once everything is set up properly, there is no maintenance whatsoever, if you know what you are doing.

baz00 3y ago
Well last time I had to fuck around was because the entire IP ranged ended up on an RBL and I couldn't deliver to half the people I needed to. Oh and then there was that time that Yahoo did its thing and asks you to fill in a web form to continue delivering to them, the URL of which is neatly hidden in an SMTP response message. If you get that form wrong or they don't like the answers they will just ignore you for 6 months.

INTPenis 3y ago

>I'll just keep my private comms off email. It's not just about keeping your private communication private, it's about relying on your e-mail address being there. As long as you use someone elses domain you're vulnerable. The big providers can shut it down whenever they want. One solution is to use a custom domain that guarantees some sort of ownership. For example certain ccTLDs have more protection for private owners of their domains. And then use providers who support custom domains.

baz00 3y ago
I've got a domain which I forward my primary address to my outlook box. I just reply from outlook.com. I've had the account since 1999.