[dozzie]

Hosting one's own e-mail server is a totally opaque random crapshot. You may not have any trouble, but some other dude or gal will get their e-mail marked as spam without any way to tell what exactly is wrong and what to change.

[simias]

Maybe https://www.mail-tester.com/ would help. Also https://mxtoolbox.com/diagnostic.aspx .

If neither of these tools highlight any issues it's pretty strange indeed.

[Belphemur]

First step when getting an ip for a server that will be a mail server is to check if the ip is not already blacklisted.

You can always get it unlisted.

After that don't start to send hundred of email by day. You need to build a reputation for your domain and ip.

As the parent comment says, set up directly spf, dkim and dmarc (also arc if you can). Rspamd can help you do that.

I've been running a personal mail server for 5 years with simply following those rules.

[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.

[pricechild]

> You can always get it unlisted.

How do you do that? The vast majority of blocklists I've interacted with have been unwilling to deal with questions, instead responding only that if you fix "something" (not always specified) automated measures will remove it from the list eventually.

In my experience it has also been extremely difficult to deal with people using blocklists. It's easy to find a bunch of people using .tor.dan.me.uk rather than .torexit.dan.me.uk "just to be safe". Frankly, I'm not sure why the former list exists in the first place other than to be an arse? What threats do entry/relay nodes pose to you?

[cyberpunk]

I worked for two very large ESPs and never really had many problems with blacklists from a deliverability perspective.

Whenever one of our mailer IPs was blacklisted by one of the big targets (hotmail, gmail, etc) it would only be for 24hours after which I'd put it back into the pools (although, at least initially perhaps for our more reputable clients to warm it back up before letting the more dodgy stuff through it again). If you host your own NS's for the sender domains flipping SPF ips/ranges is not too hard (it's all automated for us, anyway).

The big boys work that way at least in my experience. I'm sure sometimes you'd hit a 'somedomain.foo' domain which is using a blocklist style thing that their (usually inexperienced) sysadmins think prevents them from receiving spam; but they're not worth arguing with. If you're doing email at volume shifting sends to another range for that client is usually 'enough' to get them through if they care that much about that one segment to ask you to do it.

If it's not then we'd usually refund instead of trying to negotiate with such admins.

Honestly though, blacklists have never been an issue for me and I've sent a ridiculous amount of email over the last 10 years...

[skrebbel]

If I ran an evil email monopoly, I would systematically drop all email from say _half_ of the email servers out there. This way, nobody would be able to make a case that we're abusing our monopoly position, but at the same time running an email server is hard and the internet is filled with wildly varying experience reports (which is the best FUD there is).

This way, fewer people start email servers and, therefore, fewer potential competitors grow up.

Obviously I have no way to tell whether Google really does this, but if they would, the result would look exactly like this HN thread.

I'm probably totally wrong here, but note that there is absolutely no incentive for the large email providers to try to fix this mess and make email the free distributed network it once was.