Using Classic Outlook on Windows for personal email, calendar, and contact management
Hi Johnny,
I don't think this is related to your OS version. However, you could try to sign in to Outlook on Web - https://outlook.office.com/ and try to send a message with an attachment. This will help us to find out whether this is on account or app side.
If you can't send a message with attachment from Outlook on Web, please ask your admin whether there is an mail flow rule to restrict sending messages with attachment.
Best regards,
Nemanja