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Forward sent/outgoing mail and show it in correct threads/conversations

I get email in Outlook WebApp. I also happen to hate Outlook WebApp. What I want: Have outgoing emails (sent in the past) forwarded to Gmail Have those emails grouped in their appropriate ...
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Do other outlook.com users find certain domains and keywords cannot be blocked via rules? e.g. support.com, email.com

I have been using outlook.com since forever, with a hotmail address that was migrated. I've set up a ton of rules to delete spam, and most of them seem to work fine. But a few of them flat-out are ...