Hi Mark Andi and CodyMontgomery!
Thank you for posting in the Microsoft Community Forum.
I understand that you are having difficulty sending emails wherein you are getting an error message. I can only imagine the inconvenience when you can't send important documents. Let's work together to find a solution to this problem.
In the last 24 hours, there have been several users who have reported such an issue. Specifically, it's about sending an email with a PDF file as an attachment. Microsoft was aware of the issue, and our engineering team had already worked on the issue. And as of today this problem has been solved. Please check on your end if you are now able to send emails.
If you're still having this issue, please let me know so we can explore other options. This includes a workaround suggested by our engineers, which is to use a mail app like the Windows Mail app for Windows, for example. In essence, you just need to add your account to the app, and you'll be able to send an email with attachments. Please refer to this link. Set up email in the Mail app - Microsoft Support
Sincerely
ReynaldoB
Microsoft Community Forum Moderator