nhybgtvfr
I actually had some issues with Hetzner, especially when sending emails to Outlook. Gmail worked much better.
In any case, I always had to stay on top of the configurations and relied on my score at MailSpike
I never reached the full 5 points — I usually stayed around 4.75 — mainly because of DANE, since cPanel didn’t support it, and now Enhance still doesn’t support it natively (hopefully that will change soon).
Currently, I mainly use NetCup for my servers — including my main mail server — and I have a good reputation on both Talos Reputation and MailSpike, which helps a lot.
All regular emails are sent directly from my mail server; only occasional newsletters (small ones — around 100 to 500 recipients and sent infrequently) go through MailBaby.
With Gmail I have no issues — messages always reach the inbox — and I monitor everything through Google Postmaster Tools. Outlook still sends a few to spam, but fewer and fewer over time.
For blacklist monitoring, I still use this rather old-fashioned-looking site, but it’s extremely effective MultiRBL
standtech
You’re absolutely right — Microsoft applies blocks quite randomly. They’ve even blacklisted entire ranges for something as trivial as a few emails with the same subject line or a single complaint, which makes no sense.
The ironic thing is that they’re far from being an example of reliability themselves — the spam filters of Outlook.com, Hotmail, and Office365 are notoriously inconsistent.
I had a client who insisted on keeping their email hosted with Microsoft — fine by me — but now they spend their days complaining about disappearing messages. I’ve already told them:
“You’ll have to take that up with Microsoft, not with me.”
Another one eventually gave up and moved back to hosting email with us — and never wanted anything else since.
