All fastmail messages to hotmail delivered as spam
 

Using Fastmail for a while. Most mails are delivered well, however exclusively for @hotmail/@live adresses, all mails are classified by Microsoft as spam.

How is that possible? Anything needed (DKIM / SPF) is set correctly, according to fastmail. Because we're sending out messages for parties & our wedding at the moment, it's very annoying we've to check with people if these messages are delivered.

Can we we solve this? Please help :confused:

Welcome to the forums!

I suggest you submit a support request on the issue.

If you can retrieve an example received by Microsoft with the full headers, that might help to shed some light on what is going on. Before posting the headers on this board, obfuscate personally identifiable information.

Congratulations on your upcoming nuptials.

More importantly, pass the headers on to FM support.

I just sent some test messages to hotmail from a Fastmail domain and my personal domain through Fastmail and they all arrived in my outlook.com Inbox with no problems. If you are using your own domain, there are many things which might be causing this.

When examining the message as received at hotmail.com/outlook.com, look at the Authentication-Results header (example shown for message sent from Fastmail domain):

Authentication-Results: spf=pass (sender IP is 66.111.4.25)
smtp.mailfrom=fastmail.com; hotmail.com; dkim=pass (signature was verified)
header.d=fastmail.com;hotmail.com; dmarc=pass action=none
header.from=fastmail.com;

Unfortunately, hotmail/outlook does not add any other headers I can find to allow troubleshooting the reason for a message to be filed in the Junk Email folder. The most common reason would be the content of the message, which Fastmail has no control over.

Anyone receiving such an improperly filtered message at hotmail/outlook which is filed in Junk Email should click on the It's not spam link when reading the message. This is part of the message which states This message was identified as spam. We'll delete it after xx days.

Bill

This may not be your issue, but I have found that Outlook.com spam filters tend to grab many legitimate messages I want, and no matter how often I report them as "Not junk" they still go straight into Junk--even messages from other accounts I own to myself. That's one reason I use Outlook.com for only unimportant newsletters and such--no guarantee you'll actually receive mail you want to see. The only solution I have found is to periodically check the Junk folder and manually move things into the Inbox.