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How come self hosting email is such a pain in the ass? I use Proton, its okay, I feel better about it vs Gmail/Gsuite, but its no where as good, feature wise. I

How come self hosting email is such a pain in the ass? I use Proton, its okay, I feel better about it vs Gmail/Gsuite, but its no where as good, feature wise. If I could self-host email, I'd feel good about my tool stack, but I simply don't know enough about the protocols, web/mobile clients, managing network and in/outbound issues, I give up before seriously considering.

floren 3y ago
I'm also self-hosting on a different domain. The actual software stack is easy. It's dealing with the blacklists that's hard -- I submitted a ticket to spamhaus, but of course there's been no response after weeks. I guess I have to figure out how to tuck a $50 bill into an email if I really want to get off that list...
- okanat 3y ago
  If they start taking those bills, they will want to get them often. Self hosting is a lost cause for e-mail unfortunately. You either get overrun by the amount of creatively formatted spam, or all of your e-mails are dropped despite having perfect SPF+DKIM+DMARC records and long-time owned domains. Especially Microsoft has a horrible record of dropping e-mails everyone but big enough companies. Guess which software is the most popular choice in business e-mails: Microsoft Exhange. So no job applications, no communication with the various government offices, no business enquiries but loads and loads of spam that uses all possible codepoints in UTF.
  - autoexec 3y ago
    In one sense, I could kind of understand it. If they can eliminate 99% of all spam by only accepting mail from a handful of domains, and if those few domains happen to be what 99% of their users get (wanted) email from, it's hard to justify the expense and hassle of accepting mail from anyone else. That said, considering how much spam is sent from gmail and other large mail providers it seems like the actual numbers probably aren't as supportive. I don't agree with it, but I could understand it. Because of the spam/blackist problem, every ISP I've worked for has ultimately either stopped providing email service or outsourced it.
- lvncelot 3y ago
  > I guess I have to figure out how to tuck a $50 bill into an email if I really want to get off that list... You could title your mail to spamhaus: "You're today's lucky winner of $50!!!". That might get you on their good side.
bsder 3y ago
> How come self hosting email is such a pain in the ass? Because Google and Microsoft have a monopoly on email. Because of that, they don't have to play nice with anybody else and can make you jump through any arbitrary number of hoops since they hold most of the users.
- flyinghamster 3y ago
  It's very uneven, and which domain(s) you have trouble with will not necessarily be the same as anyone else's problem domains. I also self-host, no mailing lists, personal mail only, and my one and only deliverability problem is AT&T. Google? OK. Comcast? OK. Charter? OK. Hotmail? OK. Any @sbcglobal.net address, or anything else associated with SBC d/b/a AT&T? Fahgeddaboudit. I can check the public DNSBLs, and there's no problem. I can jump through AT&T's hoops, and get their automated replies, and next week I try to send to a person on AT&T and find I'm back on their secret blacklist.

floren 3y ago

I'm also self-hosting on a different domain. The actual software stack is easy. It's dealing with the blacklists that's hard -- I submitted a ticket to spamhaus, but of course there's been no response after weeks. I guess I have to figure out how to tuck a $50 bill into an email if I really want to get off that list...

okanat 3y ago
If they start taking those bills, they will want to get them often. Self hosting is a lost cause for e-mail unfortunately. You either get overrun by the amount of creatively formatted spam, or all of your e-mails are dropped despite having perfect SPF+DKIM+DMARC records and long-time owned domains. Especially Microsoft has a horrible record of dropping e-mails everyone but big enough companies. Guess which software is the most popular choice in business e-mails: Microsoft Exhange. So no job applications, no communication with the various government offices, no business enquiries but loads and loads of spam that uses all possible codepoints in UTF.
- autoexec 3y ago
  In one sense, I could kind of understand it. If they can eliminate 99% of all spam by only accepting mail from a handful of domains, and if those few domains happen to be what 99% of their users get (wanted) email from, it's hard to justify the expense and hassle of accepting mail from anyone else. That said, considering how much spam is sent from gmail and other large mail providers it seems like the actual numbers probably aren't as supportive. I don't agree with it, but I could understand it. Because of the spam/blackist problem, every ISP I've worked for has ultimately either stopped providing email service or outsourced it.
lvncelot 3y ago
> I guess I have to figure out how to tuck a $50 bill into an email if I really want to get off that list... You could title your mail to spamhaus: "You're today's lucky winner of $50!!!". That might get you on their good side.

bsder 3y ago

> How come self hosting email is such a pain in the ass? Because Google and Microsoft have a monopoly on email. Because of that, they don't have to play nice with anybody else and can make you jump through any arbitrary number of hoops since they hold most of the users.

flyinghamster 3y ago
It's very uneven, and which domain(s) you have trouble with will not necessarily be the same as anyone else's problem domains. I also self-host, no mailing lists, personal mail only, and my one and only deliverability problem is AT&T. Google? OK. Comcast? OK. Charter? OK. Hotmail? OK. Any @sbcglobal.net address, or anything else associated with SBC d/b/a AT&T? Fahgeddaboudit. I can check the public DNSBLs, and there's no problem. I can jump through AT&T's hoops, and get their automated replies, and next week I try to send to a person on AT&T and find I'm back on their secret blacklist.