I just ran through the Exchange Hybrid configuration wizard yesterday as we want to move some users to Office 365.
I am currently running through my testing and have found that the user who's mailbox exists in O365 can receive email (both from internal and external email addresses) but they cannot send to either internal or external addresses.
I don't get any non delivery reports or anything like that, the emails just fail to arrive at the recipients mailbox.
I am presuming this is a send connector issue but I am struggling to find the information I need. Can anyone help point me in the right direction?
1.) Trace the mail from O365 portal and check the trace logs and look if you find any information.
2.) Rerun the send connector called “Outbound to Office 365" and validate it and check if it throw any error.
3) Did you create any send connector manually or its the one that created automatically while running the HCW??
4) Did O365 users are able to send mails to O365 users??
5)Did you route outbound mail to external recipients from your Exchange Online organization through your on-premises organization (centralized mail transport), or route it directly to the Internet??