4 ms·

On the other side of that, sending mail to gmail can be rather challenging. They have a tendency of 541-ing mails for no apparent reason, under the pretense of

On the other side of that, sending mail to gmail can be rather challenging. They have a tendency of 541-ing mails for no apparent reason, under the pretense of "poor mail server reputation". Basically you don't control who gets to send you mails. You're entirely at Google's uncompromising and unreachable mercy.

andybak 9y ago
Is this bulk mail? (I'm not implying spam - transactional or opt-in) I only ask because I don't recall any problems over the years with one to one emails either to my gmail or from me to other people's gmail accounts.
colechristensen 9y ago
If you run DKIM, SPF, and DMARC, you shouldn't have any delivery problems. DKIM is signing your email with the public key in DNS. SPF is whitelisting which mail servers send mail from your domain DMARC is how receiving ends should report how your mail is delivered (or not). Unless you're actively spamming (ahem, "marketing") to large volumes of users, you should have no trouble at all getting mail delivered to users. If you are doing mass email marketing, stick with your core competence and let someone else handle the mail servers.
- JoshTriplett 9y ago
  If you're not careful with how you do those things, though, then you'll be unable to send mail through quite a bit of standard mailing list software. It's possible to configure some (not all) of those in a way that allows mailing lists to work, but some of them are just completely incompatible.
  - colechristensen 9y ago
    True. When it comes down to it, I'm on the side that says mailman is doing wrong when it modifies messages breaking their signatures. Here's some background https://wiki.list.org/DEV/DKIM https://wiki.list.org/DEV/DKIM
    - JoshTriplett 9y ago
      I'm not a big fan of mailing list software that modifies the non-header parts of messages. But, for instance, some of the signature schemes utterly break the ability of a mailing list to send mails on to the rest of the list members while preserving all the headers.
    - bradknowles 9y ago
      The people who designed DKIM didn't care about how mailing lists worked, they just did it anyway. But Mailman has adapted over the years, and Mailman3 is greatly improved. IMO, it's the best mailing list package out there, especially with regards to DKIM and DMARC compliance, but only if it is configured correctly. However, even that can only carry you so far. Gmail is screwed up in how they handle reputation, especially with regard to IPv6. The exact same message delivered to Gmail via IPv6 will get refused versus sending it via IPv4 will work fine. This problem has existed for years. There are even standard hacks for postfix to cause all mail addressed to Gmail to be sent via IPv4 only, just to avoid this problem. And any domain hosted with GAFYD is likewise screwed. You can't know what your false positive stats are, because you don't have access to all the remote SMTP spools or logs on the 'net. All you can know for sure is the false positives that you find out about. But you literally have no way to tell how big the iceberg is under the water.
      - lloeki 9y ago
        > But you literally have no way to tell how big the iceberg is under the water. Aren't DMARC reports supposed to tell you that, especially ruf?
        tankenmate 9y ago
        I've found DMARC reports to be incomplete or flat out lies from time to time.
- interfixus 9y ago
  You shouldn't have any problems. But you do. After fifteen years running my own mail systems, I have finally given up. Ever more outgoing mail was getting lost, despite everything being up to date and done by the book. The arch villains, over and over, were Gmail and the MS thing - Hotmail, outlook.com, Live, whatever they call it.
  - techsupporter 9y ago
    > After fifteen years running my own mail systems, I have finally given up. Same here. I've been hosting my own e-mail for two decades (as of this year) and I gave up earlier this year. My spouse's e-mail to friends who use GMail--something like 80% of them--would, every couple of months, disappear into the recipient's spam folder or sometimes just disappear entirely. My logs would show a successful delivery but the recipient couldn't find the message anywhere. Occasionally messages would start going into junk in the middle of a conversation. Nothing I changed would permanently fix it. I'd send from a different IP in my block (something.something.194 instead of something.something.193) and mail would flow again...for a couple of months and then stop. My domain registration predates Google's existence by 18 months. I've been sending from the same IP subnet for six years. My colo provider is actually so small that I'm the only customer left on my "neighborhood" /24 (they've recently asked me if I want the entire block routed to me for the lulz). I have SPF, DKIM, and DMARC all set up and they've not changed for at least two years. The amount of mail outbound from my server is (was?) so little that I could tail the outbound mail log and keep up with each message being sent. None of that mattered. I even signed up for Google's Postmaster Tools but, and this really cooked my goose, I send so little e-mail that I don't qualify to show up on their reports. I tried contacting Google but hahahahahahahahahahahaha--wheeze--hahahahahahahaha. No other recipient had a problem with me. Messages were successfully delivered to Microsoft and Yahoo just fine. Only Google had a problem with my e-mail. I finally caved. Google has SO MUCH of the e-mail market that unreachability to them is a catastrophe...and they know it. I don't have the leverage to make them play nice. Thankfully, Fastmail does so I've changed to them. For the first time since February 1997 my MX doesn't point to my own server and that makes me a little sad.
    - 9y ago
peterwwillis 9y ago
AOL and Yahoo and a bunch of other providers used to be tough as well. I don't think there is much benefit to being _less_ scrutinizing when your user base is mostly consumers.
skarap 9y ago
> They have a tendency of 541-ing mails for no apparent reason There is a reason. It makes people switch from own email servers to gmail.

andybak 9y ago

Is this bulk mail? (I'm not implying spam - transactional or opt-in) I only ask because I don't recall any problems over the years with one to one emails either to my gmail or from me to other people's gmail accounts.

colechristensen 9y ago

If you run DKIM, SPF, and DMARC, you shouldn't have any delivery problems. DKIM is signing your email with the public key in DNS. SPF is whitelisting which mail servers send mail from your domain DMARC is how receiving ends should report how your mail is delivered (or not). Unless you're actively spamming (ahem, "marketing") to large volumes of users, you should have no trouble at all getting mail delivered to users. If you are doing mass email marketing, stick with your core competence and let someone else handle the mail servers.

JoshTriplett 9y ago
If you're not careful with how you do those things, though, then you'll be unable to send mail through quite a bit of standard mailing list software. It's possible to configure some (not all) of those in a way that allows mailing lists to work, but some of them are just completely incompatible.
- colechristensen 9y ago
  True. When it comes down to it, I'm on the side that says mailman is doing wrong when it modifies messages breaking their signatures. Here's some background https://wiki.list.org/DEV/DKIM https://wiki.list.org/DEV/DKIM
  - JoshTriplett 9y ago
    I'm not a big fan of mailing list software that modifies the non-header parts of messages. But, for instance, some of the signature schemes utterly break the ability of a mailing list to send mails on to the rest of the list members while preserving all the headers.
  - bradknowles 9y ago
    The people who designed DKIM didn't care about how mailing lists worked, they just did it anyway. But Mailman has adapted over the years, and Mailman3 is greatly improved. IMO, it's the best mailing list package out there, especially with regards to DKIM and DMARC compliance, but only if it is configured correctly. However, even that can only carry you so far. Gmail is screwed up in how they handle reputation, especially with regard to IPv6. The exact same message delivered to Gmail via IPv6 will get refused versus sending it via IPv4 will work fine. This problem has existed for years. There are even standard hacks for postfix to cause all mail addressed to Gmail to be sent via IPv4 only, just to avoid this problem. And any domain hosted with GAFYD is likewise screwed. You can't know what your false positive stats are, because you don't have access to all the remote SMTP spools or logs on the 'net. All you can know for sure is the false positives that you find out about. But you literally have no way to tell how big the iceberg is under the water.
    - lloeki 9y ago
      > But you literally have no way to tell how big the iceberg is under the water. Aren't DMARC reports supposed to tell you that, especially ruf?
      - tankenmate 9y ago
        I've found DMARC reports to be incomplete or flat out lies from time to time.
interfixus 9y ago
You shouldn't have any problems. But you do. After fifteen years running my own mail systems, I have finally given up. Ever more outgoing mail was getting lost, despite everything being up to date and done by the book. The arch villains, over and over, were Gmail and the MS thing - Hotmail, outlook.com, Live, whatever they call it.
- techsupporter 9y ago
  > After fifteen years running my own mail systems, I have finally given up. Same here. I've been hosting my own e-mail for two decades (as of this year) and I gave up earlier this year. My spouse's e-mail to friends who use GMail--something like 80% of them--would, every couple of months, disappear into the recipient's spam folder or sometimes just disappear entirely. My logs would show a successful delivery but the recipient couldn't find the message anywhere. Occasionally messages would start going into junk in the middle of a conversation. Nothing I changed would permanently fix it. I'd send from a different IP in my block (something.something.194 instead of something.something.193) and mail would flow again...for a couple of months and then stop. My domain registration predates Google's existence by 18 months. I've been sending from the same IP subnet for six years. My colo provider is actually so small that I'm the only customer left on my "neighborhood" /24 (they've recently asked me if I want the entire block routed to me for the lulz). I have SPF, DKIM, and DMARC all set up and they've not changed for at least two years. The amount of mail outbound from my server is (was?) so little that I could tail the outbound mail log and keep up with each message being sent. None of that mattered. I even signed up for Google's Postmaster Tools but, and this really cooked my goose, I send so little e-mail that I don't qualify to show up on their reports. I tried contacting Google but hahahahahahahahahahahaha--wheeze--hahahahahahahaha. No other recipient had a problem with me. Messages were successfully delivered to Microsoft and Yahoo just fine. Only Google had a problem with my e-mail. I finally caved. Google has SO MUCH of the e-mail market that unreachability to them is a catastrophe...and they know it. I don't have the leverage to make them play nice. Thankfully, Fastmail does so I've changed to them. For the first time since February 1997 my MX doesn't point to my own server and that makes me a little sad.
  - 9y ago

peterwwillis 9y ago

AOL and Yahoo and a bunch of other providers used to be tough as well. I don't think there is much benefit to being _less_ scrutinizing when your user base is mostly consumers.

skarap 9y ago

> They have a tendency of 541-ing mails for no apparent reason There is a reason. It makes people switch from own email servers to gmail.