NOTE: Read my edit further down first.
There’s a similar discussion regarding Office 365 and TLS here:
http://community.quickfile.co.uk/t/using-smtp-tls-for-mail-settings/910
The .NET framework AFAIK doesn’t explicitly support TLS but setting the property enableSsl will allow for TLS communications (see here), this is something we’re already doing and can be invoked with the “use SSL” checkbox.
I’m not sure if other users have managed to configure Office 365 emails on QuickFile but any feedback would be welcome here.
EDIT:
OK this is nothing to do with SSL/TLS, I did suspect something else was going on here as if it were an authentication issue it would return an invalid authentication message, not a timeout.
As it happens it appears to be a case of IP blocking. We can actually connect to Office 365 SMTP on our local development environment but not in production. I will have a look to see where on Office 365 you can white list IPs. If you want to try this yourself it’s 5.2.17.178.