Not sure if this is part of the problem, but the way I understand the Date folders is this: whatever is in a particular Date folder will be written into the game any time you launch it with a starting in-game date that is on or after the date specified by the folder, up until you launch it with a starting in-game date that is on or after the date of the next dated folder.
So if you have a Date folder 19390901, and the next one is 19400101, everything in 19390901 will be enabled every time you load the game and your in-game date is on or after Sept 1 1939, and it will continue to add all that stuff to the game until you've played to or past Jan 1 1940, at which point it will start enabling the stuff in the next folder instead the next time you exit the game and relaunch it.
If you want files be there on one specific day and that day only, you'd have to make Date folders for each individual day in order (19390901, 19390902, 19390903, etc.). But that would only work for you if you exited and re-entered the game every time the date changed in-game, otherwise you'd still be hearing Sept 1's broadcasts on Sept 2, 3, 4, and so on, until you exited and relaunched and Commander could enable stuff from the folder that applies to whatever your new in-game date is.
(Also if you are not rolling back Commander either manually or automatically, anything written into the game during one session will remain in the game until you either remove it manually or overwrite it with a different file of the same name.)
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