This is a bit off topic as it is not directly related to SA, but I'm
hoping that with the email and spam expertise on this group, someone
might throw in a useful idea - which would be much appreciated.
I have this problem on one site where most emails we send to
Hotmail/Outlook.com/Live.com email addresses end up in Junk at the
recipient's end. Things I have tried:
1. I've setup SPF, DKIM, DMARC (and set it to 'reject').
2. We used to smart relay outbound email through the hosting provider
(1and1), but now changed to send directly from our own IP address, so
that we can control the reputation of the sending IP - no change.
3. I've checked our public IP and the domain name at mxtoolbox.com - all
tests pass (the public IP has been delisted from the Spamhaus
non-MX/end-user IP database).
4. I've setup forward and reverse DNS entries for our IP address.
5. I've checked with all DNS blocklists/blacklists I could find - our
domain or IP address is not flagged up anywhere.
6. This is a small network which I've been managing for years - the
domain name has not been used to send marketing/lists email of any sort
- so the historic reputation should be fine.
7. I've setup a monitor and block on port 25 outbound on the network
firewall - in case there is a trojan on a machine on the network sending
out spam and ruining the reputation of our IP - it's never been triggered.
8. I've checked the contents of outgoing emails - this is an accountants
practice - the email content is standard, there is nothing there which
should trigger bayesian filters.
9. I've sent emails to other servers under my control running SA - the
scores come out perfect at the receiving end.
10. The emails we send are operational and notices emails to customers -
who need them. They call on the phone and complain they haven't received
them - just to discover they were sent, but ended up in the junk.
11. Emails we send to any other domains are never a problem spam-wise.
I can't really think of anything else to try - have I missed anything?
Are Hotmail/Outlook.com spam filters a complete lottery?
