Configuring preferences and options in Outlook.com
@Greg Allshouse said
I am trying to forward my outlook.com email to another service. I have gone through the setup process, rechecked to make sure it was still shown the way I set it up and it is. I have no outstanding security issues as one recommendation that was presented stated that could be an issue and still nothing is being forwarded
You've already covered all The Usual Suspects. From here on we are in Shot In The Dark territory.
0 -- Just to be sure that the path is not blocked, use Outlook Web https://outlook.cloud.microsoft/ and do a manual forward to the target.
1 -- Turn off account auto Forwarding and try a Redirection Rule instead?
2 -- If the target is not Microsoft hosted, just as a test, change it to an outlook.com address.
If you need a test account, create a new, temporary one at https://signup.live.com
3 -- If this is a brand new outlook.com account, there are a very few reports of Mother Microsoft just flat out refusing to forward, no matter what the account settings say. If that's the case all I can suggest is to build up the "Reputation" of the account by sending and forwarding manually. But I can't tell you how long you'll have to do this before Mother turns you loose.