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Every time email is discussed here, people familiar with self-hosting point out that it’s nearly impossible to get Gmail to not flag your mail as spam. (I have

Every time email is discussed here, people familiar with self-hosting point out that it’s nearly impossible to get Gmail to not flag your mail as spam. (I have no idea, but it’s a recurring theme.)

kazinator 3y ago
They're probably talking about True Scotsman's Self-Hosting whereby your MTA is not configured to go through someone else's SMTP forwarding host, but is slugging it out on its own, sending mails directly to target mail domains, and is sitting on an IP address that doesn't have reputation for sending mail. Self-hosting like it's 1992. The wise man accepts that using a reputable forwarding host for sending is still valid self-hosting.
- TobyTheDog123 3y ago
  I'm in the process of doing this now, using Postmark's SMTP relay. Hopefully one day I'll meet their requirements for not retaining logs: 1. Account must be Approved and in good standing for at least 6 months 2. Account must be on a paid monthly plan for 6 consecutive months (or have purchase credits) 3. Account must have a lifetime sending volume of over 10,000 messages https://postmarkapp.com/smtp-service https://postmarkapp.com/smtp-service https://postmarkapp.com/support/article/1139-can-i-hide-or-disable-saving-of-message-content-in-my-activity-page https://postmarkapp.com/support/article/1139-can-i-hide-or-d...
  - deleted 3y ago
    [deleted]
- floren 3y ago
  Any forwarding host recommendations? I've long contemplated self-hosting my main email but the deliverability has always been a worry. I've also got a 10 year old VPS whose IP presumably has a pretty good reputation by this point but I'm sure it's safest to use a dedicated service.
  - kazinator 3y ago
    Nope! I use my local Big ISP, and have for 13 years. To quell your worries about a prospective service, you can try them without rushing to relying on it. Just point a mail client at their SMTP host and test for a while.
  - oefrha 3y ago
    I use Mailgun, but all the big name providers should be pretty much the same for low volume sending. Unfortunately my 9 year old VPS IP was already on a spam list when I got it, not sure if it falls off eventually.
- acumenical 3y ago
  I imagine if you have your DNS records set up strongly enough it would warm up to your MTA's IP address rather quickly, but I have not tested this for a few years now.
wkat4242 3y ago
Yes and the same with Microsoft's consumer domains like live.com, outlook.com and hotmail.com . It's a total pain, they don't trust you unless you send a lot of email. Even if you never send any spam.
nulbyte 3y ago
It's possible. Easy even. Google and Microsoft both were easy to deal with for me, and I even have a domain with a newer TLD (bar). DKIM+SPF is all it seems to take. My host was also on Spamhaus' blacklist, but no one else's. I'm not sure it mattered, but they were nice enough to remove it and reply with a snippy email about how reluctant they were to do so. No surprise there, folks at Spamhaus would block their own mother. Self-hosting email is just not that hard. It does take a bit of work, but that's why it's called DIY.
- macintux 3y ago
  “I have found it to be easy” is not the same as “it’s easy”. The former could boil down to “I’ve been lucky.” In short, I’m skeptical that, given the recurring cries of anguish I’ve seen here previously, your anecdata is universal.
- Biganon 3y ago
  It was easy for you because you were lucky. My server has SPF and DKIM and DMARC, à grade of 100% on mail-tester, and was on zero blacklist. I NEVER could send an email to a Microsoft email address and have it end up in the inbox. It was systematically flagged as spam. Microsoft's answer was to subscribe to some shitty, shady third party service to maybe, MAYBE change my reputation.
andrewaylett 3y ago
The plural of "anecdote" is not "data", but I'll throw my hat into the ring as not having deliverability issues with Gmail. I can't attest to how easy or not it might be for someone who hasn't been running a mail server for nearly 20 years, though.

kazinator 3y ago

They're probably talking about True Scotsman's Self-Hosting whereby your MTA is not configured to go through someone else's SMTP forwarding host, but is slugging it out on its own, sending mails directly to target mail domains, and is sitting on an IP address that doesn't have reputation for sending mail. Self-hosting like it's 1992. The wise man accepts that using a reputable forwarding host for sending is still valid self-hosting.

TobyTheDog123 3y ago
I'm in the process of doing this now, using Postmark's SMTP relay. Hopefully one day I'll meet their requirements for not retaining logs: 1. Account must be Approved and in good standing for at least 6 months 2. Account must be on a paid monthly plan for 6 consecutive months (or have purchase credits) 3. Account must have a lifetime sending volume of over 10,000 messages https://postmarkapp.com/smtp-service https://postmarkapp.com/smtp-service https://postmarkapp.com/support/article/1139-can-i-hide-or-disable-saving-of-message-content-in-my-activity-page https://postmarkapp.com/support/article/1139-can-i-hide-or-d...
- deleted 3y ago
  [deleted]
floren 3y ago
Any forwarding host recommendations? I've long contemplated self-hosting my main email but the deliverability has always been a worry. I've also got a 10 year old VPS whose IP presumably has a pretty good reputation by this point but I'm sure it's safest to use a dedicated service.
- kazinator 3y ago
  Nope! I use my local Big ISP, and have for 13 years. To quell your worries about a prospective service, you can try them without rushing to relying on it. Just point a mail client at their SMTP host and test for a while.
- oefrha 3y ago
  I use Mailgun, but all the big name providers should be pretty much the same for low volume sending. Unfortunately my 9 year old VPS IP was already on a spam list when I got it, not sure if it falls off eventually.
acumenical 3y ago
I imagine if you have your DNS records set up strongly enough it would warm up to your MTA's IP address rather quickly, but I have not tested this for a few years now.

wkat4242 3y ago

Yes and the same with Microsoft's consumer domains like live.com, outlook.com and hotmail.com . It's a total pain, they don't trust you unless you send a lot of email. Even if you never send any spam.

nulbyte 3y ago

It's possible. Easy even. Google and Microsoft both were easy to deal with for me, and I even have a domain with a newer TLD (bar). DKIM+SPF is all it seems to take. My host was also on Spamhaus' blacklist, but no one else's. I'm not sure it mattered, but they were nice enough to remove it and reply with a snippy email about how reluctant they were to do so. No surprise there, folks at Spamhaus would block their own mother. Self-hosting email is just not that hard. It does take a bit of work, but that's why it's called DIY.

macintux 3y ago
“I have found it to be easy” is not the same as “it’s easy”. The former could boil down to “I’ve been lucky.” In short, I’m skeptical that, given the recurring cries of anguish I’ve seen here previously, your anecdata is universal.
Biganon 3y ago
It was easy for you because you were lucky. My server has SPF and DKIM and DMARC, à grade of 100% on mail-tester, and was on zero blacklist. I NEVER could send an email to a Microsoft email address and have it end up in the inbox. It was systematically flagged as spam. Microsoft's answer was to subscribe to some shitty, shady third party service to maybe, MAYBE change my reputation.

andrewaylett 3y ago

The plural of "anecdote" is not "data", but I'll throw my hat into the ring as not having deliverability issues with Gmail. I can't attest to how easy or not it might be for someone who hasn't been running a mail server for nearly 20 years, though.