That's perhaps because you have been self-hosting that long. One of the advises given to new self-hosters these days is to start sending mail to your your friends' email accounts that are hosted by the bigtech. Then you have to contact each one and ask them to mark it as not-spam, so that some day your mails will go to their inboxes, rather than the spam folder.

Honestly, I don't think that DKIM/DMARC has made the situation any better. In fact, spamassassin and rspamd often seems to work better than their spam filters in identifying actual spam.

> Then you have to contact each one and ask them to mark it as not-spam

That presumes the email is accepted into the spam folder rather than being rejected outright at SMTP time.

You're right. I don't know the situation now, but Outlook used to behave exactly like this.

Microsoft is absolutely hell to deal with. Especially if you are hosted on Linode. They frequently ban entire linode subnets. I’ve had to resort to routing all send mail via Amazon AWS SES just because of Microsoft’s IP range bans. It’s not what I’m doing, but my neighbours.

It's funny because throughout Q1 2024 a huge range of Microsoft's own IP addresses were blacklisted by Spamcop and other blacklist providers spam/phishing attacks coming from outlook.com addresses. (Google "EX703958" (MS's issue#) for some fun reading.) They (and their enterprise customers) have been on the receiving end of the same thing they do to others.

Allegedly, Microsoft subscribes to random spam checklists like UCEProtect.

uceprotect bans entire subnets & ASNs if just one IP is suspected of sending spam.Apparently, you can pay to get your IP whitelisted for some time but it will be back on the list again. Its probably a scam/shakedown operation.

As these lists discourage self-hosting and benefit large email providers, they take their own time for fixing these issues.

Yeah they are definitely the worst of the bunch. But that's unsurprising I guess.

I haven't tried sending to Outlook, but so far I'm getting through Google with just a strict SPF and a DNSSEC domain. Very low volume, to the point I assume reputation isn't being tracked. Just an observation

That's really great to hear, I haven't self hosted since maybe 2015. I must admit I assumed things would surely have gotten worse, not better.

Definitely got worse since 2015 before seeming to get better the last year or two. At least with Gmail. So many variables though, so this is more an impression based on my own experience.