I've checked and no, it doesn't happen here. Tried with 450 passengers at KORD C16 with both jetways docked, doing Deboarding, Boarding and Pushback in this order.
Note that, on Deboarding, after all passengers has exited the plane, the crew and then the pilots will have to get out as well, so it will take some extra minutes *after* the passengers count is complete before Deboarding is really done. You'll see a message "Crew deboarded", then "Pilots Deboarded" and finally "Deboarding Complete".