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How to run your own mail server (2017)

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Re: How to run your own mail server (2017)

#61
post #22

Then you realize the true pain of having a near-zero reputation when trying to email anything to people on Gmail, Yahoo, Live, etc, etc. Expect to go to spam even if you have DKIM, SPF, and no relaying. If anyone actually knows the secret to not having your own mail-server's mail go to spam on these bigger systems, please tell, I've Googled it for years with no success.

Yes. After many years, I think the algorithm is this: If the FROMs top level domain is in the top 500 websites OR is a .edu NOT SPAM, ELSE, send to "proprietary spam filter". The "proprietary spam filter" is some random crap code that is unique to each email server company. You could spend years trying to figure out how to game "proprietary spam filter" - but it is a fools errand.

I don't think so. I see @facebookmail.com in SPAM folders way more often than you'd expect on both Office 365 and GSuite. I also see mail from Microsoft and Google filtered into SPAM on their own platforms once in a while.

Re: How to run your own mail server (2017)

#63
post #30
post #22

Then you realize the true pain of having a near-zero reputation when trying to email anything to people on Gmail, Yahoo, Live, etc, etc. Expect to go to spam even if you have DKIM, SPF, and no relaying. If anyone actually knows the secret to not having your own mail-server's mail go to spam on these bigger systems, please tell, I've Googled it for years with no success.

Agreed! I've been running my own mail server for 20+ years, and I would not recommend that anybody do this on a lark. Deliverability to GMail is a huge problem for me and has been for years. I even asked friends at Google to find out what the story was. All I got back is that the mail group was so careful/paranoid it wouldn't talk to them either. I would long ago have switched over to a vendor, but I use qmail-style…

Yahoo's disposable addresses are constructed in that form (basename-keyword@yahoo.com), but I'm not sure if they support them on business/custom domain accounts.

(The base name also has to be different from your real email address, but that's a fairly desirable feature for disposable addresses since it doesn't reveal the real address like the '+' suffix on Gmail does.)

Re: How to run your own mail server (2017)

#65
post #23

Earlier quoted context omitted.

Writing one yourself is it's own fun project!

Fun is a very curious way of putting it, considering how batshit crazy IMAP is. The rest of the involved email standards are also a huge dumpster fire. I'll let Ricardo Signes do the talking: https://www.youtube.com/watch?v=JENdgiAPD6c

If you are going to write your own webmail, use dovecot for your mail-server and then target the maildir store rather than IMAP. You will be much happier.

Re: How to run your own mail server (2017)

#66
post #22

Then you realize the true pain of having a near-zero reputation when trying to email anything to people on Gmail, Yahoo, Live, etc, etc. Expect to go to spam even if you have DKIM, SPF, and no relaying. If anyone actually knows the secret to not having your own mail-server's mail go to spam on these bigger systems, please tell, I've Googled it for years with no success.

Yea I ran into the same issue. I've got SPF, DKIM, DMAC, and reverse DNS for IPv4 and v6 and still get flagged as spam. I wrote about this a while back:

https://battlepenguin.com/tech/how-google-and-microsoft-made...

It's not as bad now, so I suspect someone at Google is finally listening, but I still don't trust the reliability of e-mail. If I sent someone an e-mail I haven't e-mailed before, I'll let them know on Hangouts/SMS/Facebook that I sent them an e-mail and to check their spam folder.

Re: How to run your own mail server (2017)

#67
post #23

Earlier quoted context omitted.

Writing one yourself is it's own fun project!

Fun is a very curious way of putting it, considering how batshit crazy IMAP is. The rest of the involved email standards are also a huge dumpster fire. I'll let Ricardo Signes do the talking: https://www.youtube.com/watch?v=JENdgiAPD6c

These days you can use JMAP instead of IMAP. It was just standardized!

https://jmap.io/

Re: How to run your own mail server (2017)

#69
I'd like to point to another smtp server, which I am using and is much easier to set up than postfix in my opinion, especially for small servers like mine: https://www.opensmtpd.org/

I'm running a personal mailserver (opensmptd, dovecot, dkim, spf, dmarc, spamassassin) for some years now and although I initially had problems with deliverability to google there aren't any (apparent) issues so far.

Also I don't understand why people keep emphasizing google's spam filter being so much better than anything else. For my personal server SpamAssassin has proved itself to be more than sufficient, its spam filtering performance is on par with Gmail's (I have a Gmail account aswell), at least for me.

Of course, Gmails spam filter works better for the billions of accounts they manage, but in order to handle the spam of a tiny mail server I'm probably not the only person who is satisfied with SpamAssassin.

Re: How to run your own mail server (2017)

#70
post #22

Then you realize the true pain of having a near-zero reputation when trying to email anything to people on Gmail, Yahoo, Live, etc, etc. Expect to go to spam even if you have DKIM, SPF, and no relaying. If anyone actually knows the secret to not having your own mail-server's mail go to spam on these bigger systems, please tell, I've Googled it for years with no success.

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