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Maybe you can speak to someone at outlook and request more "space" on the blocked senders' list? It's just a guess but it must be possible. If not, may be worth looking at different providers. I have my main email address with 1&1 and never seem to have any problems with spam/trusted sender...
We are aware of an issue with emails from the Forum to Microsoft-based email accounts (hotmail/outlook/live.com email addresses). This is being looked into currently, thanks for your patience meanwhile.