Hi micjensen,
As I understand it, users with Outlook 2011 for Mac are encountering the issue when sending emails from iPhone to them. To narrow down the issue, I’d like to collect the following information:
1. Have you tried sending emails via Outlook Web App (http://mail.office365.com/)?
2. If there are other Windows users, do they encounter the issue?
3. Do all the Mac users have the issue?
4. Will the email be received delayed in Outlook 2011 for Mac when emails sending from external addresses?
5. Considering the tag is 14, I’d like to confirm if you are using Office 365 pre-upgrade or after-upgrade. Please see Am I using Office 365 after the service upgrade?
Best Regards,
Bruce Zhou