I've followed the guides and set up a server to use for a not for profit organisation. I also used the dkim plugin and so far everything has been great. people are getting our mail, and we are getting their's. We are using ispconfig as a sort of relay. So they log into "organisation"@outlook.com. And outlook.com uses the pop account feature so send mail through our relay. Works great. Also receives fine and uses the forward function to mail back too "organisation"@outlook.com. works for nearly all domains except 1! outlook.com. If mail is sent to us from almost anywhere, it goes in the inbox. if a Hotmail sends mail to us, goes strait to junk? Like gmail sender worked fine. Can any one see why all mail that comes from Hotmail or outlook, goes strait to junk? Thanks in advance
I guess that outlook.com has some specific filter rules for their own domain names and if email arrives with a sender domain that Microsoft owns but the relay server is not owned by Microsoft, then they flag the mail as spam. What you could try is to implement srs in postfix, e.g. with postsrsd: https://github.com/roehling/postsrsd
Like I explained above, my guess is that outlook just handles their own domains (domains owned by Microsoft like hotmail.com or outlook.com) differently, so that your own email works is good but it is probably not a positive or negative indicator for the issue that forwarding for emails with hotmail sender address is seen as spam. srs is a software that might help with such problems, so its worth a try.
