Exchange 2016 Hybrid deployment

Hey all, LRL, FTP;

I am trying to deploy Exchange 2016 in a hybrid deployment where my inbound and outbound email from Exchange is routed through O365 email servers.

I have inbound email working perfectly as far as I can tell, however, I can’t seem to get outbound email working.

My ISP blocks port 25, and I can’t find any concrete answer if Microsoft will except email for this feature on a port other than 25.

They do seem to except email on port 587, but when I set the auto created send connector to that with powershell, it does work, my email doesn’t get delivered at all.

Currently I have a smart host configured to send email with 587, but I would prefer to use O365 servers if at all possible to mimic an actual hybrid deployment.

As far as I can tell, Microsoft doesn’t allow you to proxy email through someone else before it gets to them.

I did read somewhere that since it sends email from the edge server (if you have one), I could possibly find a VPS that doesn’t block 25 outbound and setup an exchange edge server. I’m not sure how practical this is however.

If you have any thoughts, let me know!

Thanks,

andents776