this post was submitted on 27 Oct 2026
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I've done that and learned a lot. Microsoft (Outlook, Hotmail) won't accept your email without paying them, or forwarding through someone who does (proton?).
i'm surprisingly ok with microslop not accepting my email actually
Thanks for making me realize that I literally don't even need to be able to deliver to MS and I can just use my mailserver 😭
As am I. i don't forward through anyone. All working well, but the learning process did, as you alluded to, give me white hairs.
noted, thank you.
while we're here, any other tips i should keep in mind? what's your stack (if you don't mind sharing)?
Postfix, Dovecot, MySQL (MariaDB), postgrey, spamassasin.
Tips:
I did mine before LLM's, so I can't comment how useful this will be, but I worry one might not understand the decisions made.
That's absolutely not true. They sometimes bork some messages and signatures internally, but aside from that, delivery to MS stuff (and that includes a lot of business behind their "outlook protection" service) has been fine for years.
And, contrary to old beliefs, it has been mostly fine all around. Just properly setup DKIM, your DMARC and SPF records, and don't actually send spam. The worst that could happen is if you're trying to send through some residential IP, as large blocks can occasionally get blocked. But a cheap hosting anywhere (even in a spamfarm-ridden provider) is very likely to work fine.
Lol no
Maybe if you've got a 10 year old domain that's been actively sending legit email everyday or something, but my email from my server goes straight to spam on outlook. Literally everywhere else is fine.
// yes my dmarc, dkim and spf are fine. No I'm not on any blocklists. No my IP is not a residential IP lol. The domain and server just turned 1 year old last week :]
Well, I must have imagined all the traffic being fine going out from an OVH server all this time then /shrug
I just looked and they've blocked the whole IP range from the VPS provider (digital ocean in this case). I assume many vps' have the same issue.
Sent a few messages to them so here's hoping.
I'm sending through a vps and have properly set up all the things (dmarc, dkim, spf, et al).
It was years ago when I set up, but I spent some time trying to get the mail to go through (wife uses Hotmail). The rabbit hole led me to a service I could purchase that would allow the mail to go through. Many fora articles paralleled my own experiences.
I don't send spam, and my "reputation" is good. I'll look into it again.