Forum Discussion
SMTP relay through Office 365 from on-prem to internet
Your current setup sounds like it should work just fine based on my experience.
There are three ways to relay mail through O365 - 1. directly using an authenticated account, 2. directly using an allowed IP address, 3. indirectly using the hybrid server. If you're planning to continue to use option 3 you shouldn't need an authentication account.
Are you running into issues with your current configuration?
Thanks for the reply.
Either I have something wrong with my config or I am missing one small detail. Here is the config:
1. I have run the HCW (without the Centralized mail transport option)
2. Right now I have two send connectors on prem - One that point tenant.mail.onmicrosoft.com to 365 and another that point * through out firewall on prem.
I have tried to change the one pointing to * to smart host - our MX record (which points to 365) or the option of 'MX records of the recipient domain'. Neither one works for me, on my device I still get authentication needed.
Not sure how the connectors need to be config'd in order to point to 365 through the Hybrid.
Thanks,
Jason H
To avoid any outages, I would create a new connector. Eventually you'll want to use a '*" address space but you can test with a specific domain for now. You should use a smarthost address for EOP (e.g. contoso-com.mail.protection.outlook.com).
You would also need a receive connector that authenticates the on-prem server using either an IP address (typical and likely the same configuration as your existing receive connector) or a certificate.
There is additional detail provided in part 2 of this article: https://technet.microsoft.com/en-us/library/dn751020(v=exchg.150).aspx#Part2configmail
Guy
Thanks for everyone help. The problem was I kept trying to test one mail server while keeping the other connectors live. Disabled all connectors, point all traffice (*) to our MX record, and SMTP is working.
Thanks again,
Jason H