Emails from Office 365 to on Premises server

[neonetman]

We are now in the final throes of setting up the hybrid side of our Exchange server. The only issue I think we are still having is that emails are not sending from the Office 365 mailboxes to on premises mailboxes. I've added 2 screenshots below to show the messages stuck on pending, and the detail below that.

 

The IP it is trying to connect to to send messages is our Spam-hero subscription, so I see no reason why emails are not going to it. I'm beating my head against a brick wall trying to resolve it so I'm hoping one of you lovely folks can help:-

 

 

 

Thanks in advance for saving my sanity

[northernmike]

Check the event logs on onprem exchange server,

Check you have send connector in place: outbound to office 365

Check receive connector have cert ssl applied.

Also use Queue viewer in toolbox to see if the queue to 365 is listed

[chaplic]

You MUST have a direct conection between O365 and your exchange servers (load balancers, reverse proxies, firewalls OK but nothing that stores-and-forwards email like spam-hero). So before you get too far fault finding that, you should consider how to set that up.

 

if you don't, you won't have hybrid, just two email systems that don't trust each other (but will swap mails)

[Roberto]

The IP it is trying to connect to to send messages is our Spam-hero subscription, so I see no reason why emails are not going to it.

 

Why on Earth are you doing that? The on-prem and O365 servers should be exchanging messages directly via the connectors the hybrid process has you set up. You should only be touching your external filtering service when mail leaves or enters your org.