Dear Breck Demers,
Thank you for your reply.
At present, New support request (office.com) this is the only form we can try. Please understand that the community does not have the authority to process user data, so we can only make the above suggestion. You can click on "Help" - "Feedback" in the menu bar on the Outlook web page to report this issue.
Additionally, you can inquire with the chat support personnel whether subscribing to Office 365 can help improve this issue.
Once again, we apologize for any inconvenience caused.
Best Regards,
Ulrica.W - MSFT | Microsoft Community Support Specialist