Example: I still have a dozen messages to Yahoo recepients sitting in O365 that are deferred. These were all sent without DKIM in the headers. Delivery is re-attemped every hour or so. After enabling DKIM, new messages go through on the first attempt. Old ones without DKIM stay stuck.
https://www.reddit.com/r/sysadmin/comments/1b9utjb/o365_emails_to_yahoocom_all_getting_deferred/

