Yes, but it depends heavily on whether your mail server has a clean IP with no spam history, the reputation of the IP range it belongs to, whether you've correc

Yes, but it depends heavily on whether your mail server has a clean IP with no spam history, the reputation of the IP range it belongs to, whether you've correctly set up DKIM/SPF records, etc. And you might have to get MS to whitelist your IP before you can send to outlook.com address, you'll only find out in your email logs whether that's the cast when you try the first time.