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Hi Aaron

I've been working through some issues related to Office365 that might well be relevant for you.

It seems that Office365 's hosted Exchange service includes all sorts of limits and "protections", so we decided not even to try to send out bulk mailings through their server. I would be very surprised if a mailing of 10,000 or more would get sent - but happy to hear otherwise.
So we send the mailings from the web-server (it's a dedicated server with ample resources to handle the bulk mailing). We set the SPF record on the domain name to allow mail from the webserver's IP address as well as from the MX server/s.

However Office365 stops any messages coming from the web-server which have a From: address of 'ourdomain.org' from reaching any of our Office365 mail accounts (which have the same domain name). There doesn't appear to be any fix for this, and the help available from Office365 appears to be either non-existent or uninformed.

We are currently working with a cludgy workaround whereby we are using external mail forwarding addresses for these internal users so that CiviMail sends messages to the forwarding addresses, which then forward on to the Office365 address, thereby bypassing Office365's dumb filter.

In our case we are sitting tight with the cludgy solution as we expect that we'll move to an Exchange server that we have control over, and so be able to configure to not exhibit such dumb behaviour.

I'm keen to learn of any experience others might have with Office365 and mail.

I've got a site hosted on CiviHosting that sends email via php's mail().  This is a setup I found that works with the help of their network guy.

-Microsoft has assisted me to setup the CatchAll mailbox to go to mymailbox@domain.org  Microsoft does not officially support a catch all mailbox but provided me a creative workaround including creating a distribution group called “All Users” then adding all mailboxes into this group then creating  a rule that anything send from outside the organization will be forwarded to mymailbox@ except if they are a member of the “All Users” group

Note:  From NOW ON, when creating a new email user for your domain, you MUST add them to the newly created group “All Users” in o365 so they DO NOT go into the catch all mailbox!!

o365 can configure a mailbox for POP.  It is then checked using these settings, configure them in your CiviMail bounce processing account.