There are issues with sending email with Office365 (and GMail) because QlikView doesn't properly support the security protocols they use.
I'm not sure if the same issues will be affecting using Qlik Web Connectors when sending.
Here is a link to a post which describes how a tool called STunnel can be used to act as a proxy, effectively allowing you to send to a local SMTP host with no SSL security which is then relayed onto another host on a different port:
Be aware that if you have something already on port 25 on your local machine you may need to use a different port.
Hope that helps.