On 19/09/17 17:17, Jerry Malcolm wrote:
My recommendation as a first step is to go to mail-tester.com. They will tell you to send an email to a temp email address, and they will analyze and grade your email as to 'spamy-ness'. Outlook, gmail, etc were flagging a lot of my emails.  After I finally fixed everything and got mail-tester.com to give me a perfect score, I haven't had any problem with getting flagged.

Hi - and thanks for the suggestion. I've tried in the past another similar service - and now I've tried mail-tester.com - it returned a score of 10/10




Jerry


On 9/19/2017 1:44 AM, G Roach wrote:
Microsoft use their own methods of detection including based on reputation and 'length of service' - ie, if you have only just started sending emails out from your own address (which you have) then they may well consider you suspicious. Theres not much yo can do about it.   More info here: https://mail.live.com/mail/troubleshooting.aspx



On 19/09/2017 07:25, Sebastian Arcus wrote:
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?


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