I guess I have never looked at HISTORY. But there is a bug, well, two in the way DATES are recorded. Some dates are recorded in 2013, yes, SIX YEARS ago. That might mean the system can't deal with those older dates or they are showing up in your history much earlier than you expect. The other date bug seems to show images, at least in my case, as from the date of my last flights, not the current date. So for me, flights taken on March 20 showed up with dates of March 8. That might also cause issues with history or where flights show up.
Again, this might not be the issue but it could be. DJI is aware and working on an update.
Some have found that manually setting the time/date just before flying might fix it as long as you don't turn off the controller.