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Outlook won't send email Office 365 hosted Exchange

Hi folks. I just migrated off a Juniper SSG 5 to UTM so I'm new to the product. I'm having a weird problem with my Outlook 2016 client and my Hosted Exchange instance.

 

Everything in Outlook seems to function properly, but it hangs up when trying to send email.

 

I resolve autodiscover.mydomain.com in DNS fine and Wireshark shows lots of activity with Exchange, but its encrypted.

 

 I found a number of posts discussing routing inbound mail through UTM before delivering to the client, but I'm not interested in doing that. This problem is purely the Outlook client behind UTM 9 connecting to Exchange.

 

I created a firewall rule allowing all ports from the host running Outlook to any IP, but it still doesn't work.

 

Any thoughts?



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