Emails being flagged as spam

v3
#1

My emails are being flagged as spam from my VPS with easyengine installed e.g., automated logwatch reports. I am hosting my emails with Outlook.com with a custom domain name. So when logwatch sends a report to ‘webmaster@mydomain.com’ the email says the sender is ‘root@server1.mydomain.com’ and flags it as spam. The root user account on my VPS ‘root’ and the hostname for the server ‘server1.mydomain.com’. Also when i was setting up Outlook.com for email i did enter the provided SRV,TXT and MX records.

Can someone help with this problem?

#2

Can you check if your domain/IP is on blacklist? - http://mxtoolbox.com/blacklists.aspx

#3

It did that check after reading your tutorials on Postfix. The IP/domain name is not blacklisted. I am wondering if Outlook.com is being overly aggressive with it spam detection. I normally see alot of emails from new companies flagged as spam

Can set the default email address Postfix uses to something like 'webmaster@mydomain.com' which is being hosted with outlook.com

#4

I got it sorted out but emails are still flagged as spam but i am not longer concerned. The email server Microsoft uses with my outlook email is on an email blacklist. So i think outlook.com is flagging my emails as spammed because that server is blacklisted

#5

Thanks for update.

As a test, you may remove server from blacklist and check if mails doens't get flagged as spam.

#6