Office 365

Hi Kristina, we have also just started evaluating Office 365 and not got into all the details yet. But our tentative plan is to keep on using use our existing Exchange server for SMTP relay  while we migrate  all our mailboxes to Office 365 online. So we don't have to change Database Mail or any other application confguration.

An alternate is to setup SMTP relay for Office 365. You can find the details here:  https://technet.microsoft.com/en-us/library/dn554323(v=exchg.150).aspx. In that case we may have to update our current Database Mail and other application configuration to reflect the new server name.

Best,

Mo

National Ballet of Canada

Hi Guys,

We are in a similar situation to you both. We are moving to Office 365 in the next few months.

We are fact finding the migration at the moment so it's good to know about he SMTP relay (thanks Mo).

If I find out any other info as we progress I'll update here.

cheers,

Dara

We also use Office 365, and went through these same issues when we set it up about a year ago.  We got rid of Exchange altogether, and set up an SMTP relay in IIS on our gateway server.  You can then use the smart host options in IIS to relay through a specifically configured mailbox on Office 365, and use security groups with Send As rights configured for different/custom sending e-mail addresses.

There was a great Microsoft KB article on this, KB2600912, but for whatever reason, it isn't coming up right now.  You might try http://www.messageops.com/office-365-tools-resources/smtp-relay-with-office-365/.

For external e-mails like TNEW confirmations, you are going to want to make sure you have a DNS pointer (PTR) record for the public IP address of whichever internal server you relay through.  I found out the hard way that if you don't have a full reverse lookup path corresponding to the message header, your messages can get bounced as spam or forgeries depending on how much security the receiving domain is applying.