The recipient is an iCloud user. That's not outgoing, that's incoming to iCloud, which is the OP's issue. His issue is sending from a non-icloud address to someone who is receiving at iCloud.
The image you posted is for mail rules, which has nothing to do with server sided spam filtering. Those are user created...again, not the OP's issue.
I think you're failing to understand the actual issue you're posting to.
Edit -----------
Ok, I see what you're saying about the "outgoing". This is assuming the issue is with the ISP doing the filtering, and not iCloud. If the filter is from the ISP, then yes, that would be outgoing. If it's from iCloud, then it would be incoming. I was only ever talking about iCloud doing server sided spam filter, which is why I'm saying the issue is potentially incoming. Sorry about the confusion with that, but it's hard to really say if it's an outgoing (from ISP) or incoming (to iCloud) issue. It could be either one.
Message was edited by: Imp68