4 ms·

There is a hidden cost to this though. Running your own email server, or even having a lesser-known company manage your email server, can cause your emails to b

by exac 5y ago

There is a hidden cost to this though. Running your own email server, or even having a lesser-known company manage your email server, can cause your emails to be sent to spam without any action on your part. You aren't notified when your email goes to a spam folder, so you always have to worry that the recipient of your emails didn't receive the email, even if you only ever send legitimate emails. If you stay on top of all the best-practices for running your own mail server, your hidden cost is the mind-share that that takes.

judge2020 5y ago
In theory this shouldn't be a problem if you aren't using a known-trash IP and have SPF and DKIM set up, since the only thing the major inbox providers want is a way to verify and associate spam reputation with a domain instead of an IP. If this really hurts you can just set up Amazon SES use that via SMTP, you'll get 62k free emails a month (always free, not just first 12 months). This even works if you want a mostly-free setup: you have MX forwarding via some provider (Cloudflare, your registrar, etc) going to a personal address, and SES operates as your outbound SPF that works with Outlook/Gmail in terms of allowing you to set your domain email(s) as aliases within their interface.
- croutonwagon 5y ago
  Thats not entirely true. Microsoft is crazy on what it flags, and their AI straight just does "things". Their support has admitted as much when i had tickets open for months trying to white list basic GNU/Hurd list serves (that I didnt run). Im sure just running Mail in a Box on linode would 100% flag it. I KNOW google would because half the time i socks through one of my linodes (that i have used and owned the IP for years on) i get thrown through all sorts of captchas on services. INCLUDING signing into my own gsuite from it (despite an established history of just doing it). Unfortunately the big players own mail, they do what they want. In fact having a domain registered with one will do better for your mail reputation than most would care to admit. Just look at how MS uses SMTPS on port 25, sure they COULD use 587 or 465, but they dont: https://docs.microsoft.com/en-us/exchange/mail-flow-best-practices/use-connectors-to-configure-mail-flow/set-up-connectors-to-route-mail https://docs.microsoft.com/en-us/exchange/mail-flow-best-pra...
  - mindslight 5y ago
    I run postfix on Debian on a longstanding Linode, haven't gotten around to setting up DKIM, and emails to businesses served by outlook.com go through just fine. I'm not rejecting the concern or the ambiguous worry about arbitrary judgement, but the surveillance web's captchas are much more draconian than spam filters.
    - croutonwagon 5y ago
      You are probably right to an extent and I was probably over dramatizing it with the whole 100% part. But having managed email across all three providers. Microsoft does just ignore rfc’s and basic standards pretty regularly and relies heavily on “AI”. Google less so. And when it works it works great. But once you get deliverability issues it’s a pain to resolve with them. Especially if you have to engage support.
      - judge2020 5y ago
        > Especially if you have to engage support. If i'm running an email inbox, responding to support regarding email deliverability is my lowest priority primarily because, if I respond once, it becomes an attack vector for dedicated spammers to try to extract information about the spam detection systems.
        croutonwagon 5y ago
        Thats more or less an argument FOR using one of the large providers. Frankly you are more likely to make exceptions and monitor internally for deliverability from a google, or outlook.com or comcast.net than for some random xyz.email domain. And blocking swaths of those has a bigger impact. Frankly though, imho, you should respond to users that report deliverability issues on your domain and tweak your spam filters accordingly. Just ignoring a users saying "i am not getting expected emails from this listserve" is a great way to encourage your users to employ shadow IT and just use personal accounts. Obscurity isnt security, even with spam mitigations. Things like SPF, DKIM, DMARC along with some user impersonation filtering (including spoofing from fields) is basic spam 101 and will catch 99% of your actual security related phishing.And the largest ones (dmarc) can be probed publicly anyhow since almost all of it relies on DNS txt records.
sschueller 5y ago
The hidden cost of me keep using google is that all my mail is stored who knows where, can be take away at anytime, is read by who knows what and pricing may change at anytime as it has with this "will always be free" version...
3np 5y ago
I am surprised that people here still have this all-or-nothing approach when it comes to managed vs self-hosted e-mail despite it being covered countless times. If what you mention does turn out to be an issue, or you decide it's a worthwhile tradeoff to not have to care about IP reputation, you can choose to route all or a subset (depending on destination domain) of your outgoing mail through a provider like mailroute/mailgun/sendgrid/fastmail/posteo. Or even gmail/AWS. You can still self-host the rest even if you don't want to hother with outgoing SMTP, which you can always add later should uou choose to. > If you stay on top of all the best-practices for running your own mail server, your hidden cost is the mind-share that that takes. Are you actually speaking from experience here? Over the past 20-30 years it's been like, what, 4-5 new things to learn?

by exac 5y ago

judge2020 5y ago

In theory this shouldn't be a problem if you aren't using a known-trash IP and have SPF and DKIM set up, since the only thing the major inbox providers want is a way to verify and associate spam reputation with a domain instead of an IP. If this really hurts you can just set up Amazon SES use that via SMTP, you'll get 62k free emails a month (always free, not just first 12 months). This even works if you want a mostly-free setup: you have MX forwarding via some provider (Cloudflare, your registrar, etc) going to a personal address, and SES operates as your outbound SPF that works with Outlook/Gmail in terms of allowing you to set your domain email(s) as aliases within their interface.

croutonwagon 5y ago
Thats not entirely true. Microsoft is crazy on what it flags, and their AI straight just does "things". Their support has admitted as much when i had tickets open for months trying to white list basic GNU/Hurd list serves (that I didnt run). Im sure just running Mail in a Box on linode would 100% flag it. I KNOW google would because half the time i socks through one of my linodes (that i have used and owned the IP for years on) i get thrown through all sorts of captchas on services. INCLUDING signing into my own gsuite from it (despite an established history of just doing it). Unfortunately the big players own mail, they do what they want. In fact having a domain registered with one will do better for your mail reputation than most would care to admit. Just look at how MS uses SMTPS on port 25, sure they COULD use 587 or 465, but they dont: https://docs.microsoft.com/en-us/exchange/mail-flow-best-practices/use-connectors-to-configure-mail-flow/set-up-connectors-to-route-mail https://docs.microsoft.com/en-us/exchange/mail-flow-best-pra...
- mindslight 5y ago
  I run postfix on Debian on a longstanding Linode, haven't gotten around to setting up DKIM, and emails to businesses served by outlook.com go through just fine. I'm not rejecting the concern or the ambiguous worry about arbitrary judgement, but the surveillance web's captchas are much more draconian than spam filters.
  - croutonwagon 5y ago
    You are probably right to an extent and I was probably over dramatizing it with the whole 100% part. But having managed email across all three providers. Microsoft does just ignore rfc’s and basic standards pretty regularly and relies heavily on “AI”. Google less so. And when it works it works great. But once you get deliverability issues it’s a pain to resolve with them. Especially if you have to engage support.
    - judge2020 5y ago
      > Especially if you have to engage support. If i'm running an email inbox, responding to support regarding email deliverability is my lowest priority primarily because, if I respond once, it becomes an attack vector for dedicated spammers to try to extract information about the spam detection systems.
      - croutonwagon 5y ago
        Thats more or less an argument FOR using one of the large providers. Frankly you are more likely to make exceptions and monitor internally for deliverability from a google, or outlook.com or comcast.net than for some random xyz.email domain. And blocking swaths of those has a bigger impact. Frankly though, imho, you should respond to users that report deliverability issues on your domain and tweak your spam filters accordingly. Just ignoring a users saying "i am not getting expected emails from this listserve" is a great way to encourage your users to employ shadow IT and just use personal accounts. Obscurity isnt security, even with spam mitigations. Things like SPF, DKIM, DMARC along with some user impersonation filtering (including spoofing from fields) is basic spam 101 and will catch 99% of your actual security related phishing.And the largest ones (dmarc) can be probed publicly anyhow since almost all of it relies on DNS txt records.

sschueller 5y ago

The hidden cost of me keep using google is that all my mail is stored who knows where, can be take away at anytime, is read by who knows what and pricing may change at anytime as it has with this "will always be free" version...

3np 5y ago

I am surprised that people here still have this all-or-nothing approach when it comes to managed vs self-hosted e-mail despite it being covered countless times. If what you mention does turn out to be an issue, or you decide it's a worthwhile tradeoff to not have to care about IP reputation, you can choose to route all or a subset (depending on destination domain) of your outgoing mail through a provider like mailroute/mailgun/sendgrid/fastmail/posteo. Or even gmail/AWS. You can still self-host the rest even if you don't want to hother with outgoing SMTP, which you can always add later should uou choose to. > If you stay on top of all the best-practices for running your own mail server, your hidden cost is the mind-share that that takes. Are you actually speaking from experience here? Over the past 20-30 years it's been like, what, 4-5 new things to learn?