@Chelsea MMC your post suggests that your firm were strong outlook users prior to coming to Smokeball. I think the Smokeball Calendar sync to Outlook is not designed to be used the way you are using it but there is a Smokeball centric workflow to achieve the same outcome.

AFAIK your Outlook addin for smokeball will put items on YOUR calendar but not on other users calendars - at least my firm has never used it this way. Instead, you can create calendar events in Smokeball for your attorney’s calendar and add reminders there. If the Attorney has synced their smokeball and outlook calendars (and the sync is working correctly/hasn’t broken) then they will get the event on their outlook calendar, but the reminder will come through the PC Smokeball application.

Jonathan is correct.  You can only sync a calendar in Outlook to the user you are logged in as in Smokeball.  You can open Smokeball and Outlook on the attorney’s computer and do a sync there.