Outlook 2010 crashes when attaching files using outlook or Sharefile attach button.

I'm not really able to reproduce this. At some point hitting the attach button causes outlook to crash. Then Outlook keeps crashing whenever the attach button is pressed (outlook or the SF plugin's button). At some point it stops. A couple days ago I ran a repair on outlook after this happened and it continued until I uninstalled the sharefile plugin. So I installed the latest plugin and it would happen until I enabled it. Then it worked again for a couple days until today when it's happened again. Any idea what would cause this? It works fine on our other computers with outlook 2010 (though they have Windows 7 and not Windows 10 ad this computer has).