Fighting with deliverability issues to Outlook.com
Finally got it figured out (again), but a few things still need to be updated in code. Long version: Many, many months ago, I figured out how to get mail to the Inbox in Outlook.com. If you search Google, you'll see it's notoriously difficult as Outlook.com randomly bans IP addresses, and doesn't de-list IPs even with reasonable requests. Figured out a long term solution to this today.
Short version: Do not recommend Outlook.com's email service. They will randomly drop legitimate emails, and most end up in spam when it shouldn't.
Short version: Do not recommend Outlook.com's email service. They will randomly drop legitimate emails, and most end up in spam when it shouldn't.