Welcome to the Hubspot Community @ISCworldclass!
Sorry for all of the homework assignments, I just want to make sure I have a full picture of what is happening.
Thanks for helping.
Have you tried uninstalling and re-installing the Hubspot Sales Outlook Add-in? I know this probably sounds pretty elementary and it might not be the solution, but we have found it to successfully resolve some of the strange Hubspot Sales/Outlook issues.
I'm going to do some research, but let me know if that changes anything.
Let me know if this helps.
I hope this helps!