Using Classic Outlook on Windows for personal email, calendar, and contact management
Hi, Jacob Vanator
Good day!
Thank you for posting to Microsoft Community. We are happy to help you!
According to your description, the issue of your concern that your created printing rules no longer work on your Outlook desktop client.
For narrowing down this issue, could you be kindly to provide us the screenshot of your Outlook's office account page by open Outlook > File > Office account.
Here are the steps to open private messages:
To view private messaging options> click your profile picture at the top on the right > select the My Profile option. Click View private message(I have sent a message to collect the information.
We appreciate your cooperation on this post. Thank you.
Sincerely,
Alex | Microsoft Community Moderator.