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I've self-hosted email on and off since the mid 2000s and my impression is that with the widespread adoption of DKIM/DMARC, the large providers have toned down

I've self-hosted email on and off since the mid 2000s and my impression is that with the widespread adoption of DKIM/DMARC, the large providers have toned down the spam-by-default treatment of small/unknown email servers. Even Microsoft a bit, though you still have to get your IP whitelisted to send to outlook.com addresses usually.

ehnto 2y ago
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.
- durakot 2y ago
  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.
VladVladikoff 2y ago
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.
- durakot 2y ago
  Yeah they are definitely the worst of the bunch. But that's unsurprising I guess.
- velcrovan 2y ago
  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.
- devsda 2y ago
  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.
goku12 2y ago
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.
- zimpenfish 2y ago
  > 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.
  - goku12 2y ago
    You're right. I don't know the situation now, but Outlook used to behave exactly like this.
petee 2y ago
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

ehnto 2y ago

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.

durakot 2y ago
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.

VladVladikoff 2y ago

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.

durakot 2y ago
Yeah they are definitely the worst of the bunch. But that's unsurprising I guess.
velcrovan 2y ago
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.
devsda 2y ago
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.

goku12 2y ago

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.

zimpenfish 2y ago
> 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.
- goku12 2y ago
  You're right. I don't know the situation now, but Outlook used to behave exactly like this.

petee 2y ago

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