I’m please to announce that Microsoft have asked me to speak on “Everything You Need To Know About SMTP Transport for Office 365” at TechEd Europe 2014 in Barcelona. Its going to be a busy few weeks as I go from there to the MVP Summit in Redmond, WA straight from that event.
My session is going to see how you can ensure your migration to Office 365 will be successful with regards to keeping mail flow working and not seeing any non-deliverable messages. We will cover real world scenarios for hybrid and staged migrations so that we can consider the impact of mail flow at all stages of the project. We will look at testing mail flow, SMTP to multiple endpoints, solving firewalling issues, and how email addressing and distribution group delivery is done in Office 365 so that we always know where a user is and what is going to happen when they are migrated.
Compliance and hygiene issues will be covered with regards to potentially journaling from multiple places and the impact of having anti-spam filtering in Office 365 that might not be your mail flow entry point.
We will consider the best practices for changing SMTP endpoints and when is a good time to change over from on-premise first to cloud first delivery, and if you need to maintain on-premises delivery how should you go about that process.
And finally we will cover troubleshooting the process should it go wrong or how to see what is actually happening during your test phase when you are trying out different options to see which works for your company and your requirements.
Full details of the session, once it goes live, are at http://teeu2014.eventpoint.com/topic/details/OFC-B350 (Microsoft ID login needed to see this). Room and time to be announced.
Great and refreshing session thanks for it.
Unfortunately there was a big crowd afterwards so had not got the time personally ask you questions.
Thanks – you can ask your question here if you like
Sorry for the late reply been a bit busy on a project.
In your session you mentioned we cannot have a SMTP device/smarthost between o365 and on-prem Exchange cause this breaks TLS.
When i spoke with Michael Van Horenbeeck he mentioned you got this working with a SMTP/smarthost.
As in my demo environment my ISP blocks/added my IP to blacklist (dynamic IP provider) I need to send via SMTP/smarthost.
Can you elaborate a bit how you got this fixed perhaps?
Not sure what Michael was talking about! I have never attempted to get around the support conditions required for Hybrid. It is not supported to have any SMTP smarthost/gateway between your on-premises Exchange servers and your Office 365 tenant for internal mailflow. It is fine when sending to external recipients.
Its not that it breaks TLS (though it might), it is a restriction because you need certain SMTP headers to remain intact and Microsoft cannot guarantee that all SMTP smarthosts will do this, and so no smarthosts are supported.