I have a new domain set up with Google Apps for Work. I am sending emails from "me@[domainname].com" to my outlook.com email box.
They are legitimate emails. One is a sample of a letter I'm going to send to job recruiters. One is a sample of a cover letter in the body and my resume as a PDF. Both going to the spam filter.
I have tried sending to other outlook.com emails as well, and most of the time it's marked as spam.
My domain uses SPF and DKIM, and I'm sure it's correct. I'd be willing to provide any part of the header necessary.
I am using my outlook.com email as a test bed to make sure my emails from "me@[domainname].com" are not getting marked as spam to all the people I send them too. And I assume if outlook.com is marking them as spam, lots of other recipients of mine will have them marked as spam.