Can't get email notifications to work.

Question

Anyone who can help me figure out why my email notifications won't work? I'm using the same email config that I use on other servers and they work just fine. 
 I'm using Microsoft hosted Exchange, and I am using :- 
 
 Mail Server : smtp.office365.com Port : 587 
 Username my usual 
 Password my usual 
 Connection/Security (I've tried all options!) 
 Certificate - I've tried Appliance Certificate and None 
 I get an error saying failed to connect to mail server. Do I need to create a rule or something? I have the Webfilter off and I have the Application filter set to Allow All, but I also set that to None too just in case.

Michael McQuillan · Answer

Not sure if this helps but I am just starting setting up our XG and I came across the same issue. 
 As a workaround, I have installed an SMTP relay via IIS 6 on a server (2008) internally to our domain and pointed the SMTP settings to this and its working. 
 Details about setting up an SMTP relay on Server 2008 can be found here: https://support.office.com/en-gb/article/How-to-configure-IIS-for-relay-with-Office-365-eb57abd2-3859-4e79-b721-2ed1f0f579c9 
 Only limitation is the email address sending has to match in both the relay and the settings, but this shouldn't be a massive problem. 
 Might help someone until its fixed.