Using Classic Outlook on Windows for personal email, calendar, and contact management
Sorry to hear that your messages are no longer being delivered as expected. Could you please let me know whether you receive any Non-Delivery Report (NDR), bounce message, warning, or error after sending, or whether the messages remain in Sent Items without any indication of a problem? If you receive an NDR, please share the exact error code and wording, removing any personal information.
Also, does the problem affect recipients at all providers, or only some of them? Please try sending a normal message to a single recipient who previously stopped receiving your newsletter and ask them to check both their Inbox and Junk/Spam folder.
It would also be useful to know whether the same result occurs when sending directly from Outlook.com in a web browser instead of Classic Outlook.