[dozzie]

I've been running a personal mail server for twice as long with simply following those rules and my e-mail is still tagged as spam in Gmail when it's me who initiates contact (once the other party sends me an e-mail, reply or otherwise, I no longer get tagged as spam).

As I said, it's totally opaque crapshot.

[orangetowel]

I'm in a similar boat. I've moved ISPs a few times throughout the years, and each move it takes a few months to finally get things settled. I'm in the US, and had the best luck for deliverability when I was on a Comcast Business account.

My current ISP, a local fiber provider, was not great getting going. Most of the IPs that they have are in at least 1 spam database, and it took a while for the ISP to reach out to the database maintainers themselves. Even then, since they're a small ISP, the IPs are still blacklisted. The ISP wasn't even a company when the IPs were added to these blacklists.

After a few months they were able to assign me an IP that wasn't in a blacklist somewhere. I still randomly have issues with the big providers though - gmail is probably the most annoying. Like dozzie, my SPF, DKIM, and DMARC setups are all valid.

Overall, I really enjoying running my own mail server. Every now and then there are a few annoyances, but it's worth it in the long run.

[j_s]

There have been a few discussions regarding deliverability:

Why does Gmail hate my domain? | https://news.ycombinator.com/item?id=9855030

How to Avoid Spam Filters | https://news.ycombinator.com/item?id=10465639

Hotmail | https://news.ycombinator.com/item?id=14210939

ESP | https://news.ycombinator.com/item?id=14201704

If there are others I'd appreciate a link as I try to connect them!

[cyberpunk]

Are you using DKIM and SPF properly? I've never had any problems with this (although, I'm not mailing from home ISP ranges)

[dozzie]

Yes.

[cyberpunk]

That's very strange, then.

I'd recommend trying http://dkimvalidator.com/ to make sure everything is perfect; having proper certs on your MXs seems to help too.

I run a pretty large email infra (~500k/minute) and I'd help you out if I can...

If you're still having problems with all that in place then why don't you just change IPs?

[dozzie]

As I said, Gmail is opaque with regard to its spam detection.

As for your help offer, thank you, but I'm good. It's usually other people who want to contact me, I rarely send the first message ever.

[cyberpunk]

Hmm well, I've found it to be pretty straightforward, I'm curious why this is happening to you though and there must be a solution...

I mean.. If you get a solid result from dkimvalidator but google is still shitlisting you then I'd definitely consider moving to another host/dc/isp at least.

Depending on your size, it might be best just to make this someone else's problem (if you can) -- like google, o365, etc..

[e12e]

The real problem is Google is opaque in dropping such mail in recipients spam folder. Hotmail can sometimes be annoying in this regard too. As far as I've managed neither does the sane thing and add a header that report on how they've divided that "this mail is spam" - so the recipient doesn't have anything to go on either, other than hoping "mark this as bot spam/add to address book/send email/reply to address" help Google/Ms treat it as "not spam".

Maybe it's worse for non-English mail (maybe the statistical models are biased against "not English" even for people whom don't have English as a native language).

But I'm quite convinced google's (and to a lesser extent Hotmail/ms') "magic" spamfiltering is subtly (but annoyingly) broken.

[dozzie]

I'm definitely not giving to somebody else my /var/log/mail.log, IMAP/Mutt access, sieve rules, nor ad hoc dedicated aliases for every website account I create. And on top of that, I would land on some US-based server for ease of illegal spying and my mail would be harvested for some advertising crap, all to solve something that is not a problem for me. Not happening.