At the end of the 3-part comics series, which are the events after the final episodes, the operative is sent after River and Simon. So the breakout hologram scene must refer to events before the series. However the operative is in the current timeframe, he is viewing a past event. Also it is known that Simon spent “years" getting the clearances to gain access to River, something that could not have happened aftwrafter the evntsevents of the series, since he was a known “fugitive" by that time.