Transiting Chiron square your natal Moon is a period, usually several months to more than a year, when Chiron, the asteroid that marks an old wound and where you later help others with the same thing, sits 90 degrees from the Moon in your birth chart. The Moon is your inner weather: what you need to feel safe, and how you react before you think. A square is two points that will not fit in one day, two needs pulling at different angles. What this transit does is put those two things in the same room and close the door.
Because Chiron turns retrograde every year, it often crosses the exact square degree three times, which is why the transit stretches out the way it does. You get one pass, then Chiron backs up and crosses again, then one last forward pass. That triple crossing is not cruelty; it is the transit giving you more than one look at the same thing.